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Biginelli reaction

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Rovnyak, G. C.; Atwal, K. S.; Hedberg, A.; Kimball, S. D.; Moreland, S.; Gougoutas, J. Z.; O'Reilly, B. C.; Schwartz, J.; Malley, M. F. (1992). "Dihydropyrimidine calcium channel blockers. 4. Basic 3-substituted-4-aryl-1,4-dihydropyrimidine-5-carboxylic acid esters. Potent antihypertensive agents".
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This scheme begins with rate determining nucleophilic addition by the urea to the aldehyde. The ensuing condensation step is catalyzed by the addition of acid, resulting in the imine nitrogen. The β-ketoester then adds to the imine bond and consequently the ring is closed by the nucleophilic attack
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El Maatougui, Abdelaziz; Azuaje, Jhonny; González-Gómez, Manuel; Miguez, Gabriel; Crespo, Abel; Carbajales, Carlos; Escalante, Luz; García-Mera, Xerardo; Gutiérrez-de-Terán, Hugo; Sotelo, Eddy (2016-03-10). "Discovery of Potent and Highly Selective A2B Adenosine Receptor Antagonist Chemotypes".
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Crespo, Abel; El Maatougui, Abdelaziz; Biagini, Pierfrancesco; Azuaje, Jhonny; Coelho, Alberto; Brea, José; Loza, María Isabel; Cadavid, María Isabel; García-Mera, Xerardo; Gutiérrez-de-Terán, Hugo; Sotelo, Eddy (2013-10-03).
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Song, Dailei; Wang, Runxia; Chen, Yongli; Zhang, Shaohua; Liu, Chunsheng; Luo, Genxiang (2008). "Copper(II) trifluoroacetate catalyzed synthesis of 3,4- dihydropyrimidin-2(1H)-ones under solvent-free conditions".
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Hu, E. H.; Sidler, D. R.; Dolling, U.-H. (1998). "Unprecedented Catalytic Three Component One-Pot Condensation Reaction: An Efficient Synthesis of 5-Alkoxycarbonyl- 4-aryl-3,4-dihydropyrimidin-2(1H)-ones".
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Kappe, C. O. (2000). "Highly versatile solid phase synthesis of biofunctional 4-aryl-3,4-dihydropyrimidines using resin-bound isothiourea building blocks and multidirectional resin cleavage".
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Folkers, K.; Johnson, T. B. (1933). "Researches on Pyrimidines. CXXXVI. The Mechanism of Formation of Tetrahydropyrimidines by the Biginelli Reaction1".
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Kappe, C.O. (1997). "A Reexamination of the Mechanism of the Biginelli Dihydropyrimidine Synthesis. Support for anN-Acyliminium Ion Intermediate1".
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has reported first enzymatic synthesis for Biginelli reaction via yeast catalysed protocol in high yields. The reaction has also been reported
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Wipf, P.; Cunningham, A. (1995). "A solid phase protocol of the biginelli dihydropyrimidine synthesis suitable for combinatorial chemistry".
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Folkers, K.; Harwood, H. J.; Johnson, T. B. (1932). "Researches on Pyrimidines. Cxxx. Synthesis of 2-Keto-1,2,3,4-Tetrahydropyrimidines".
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The reaction mechanism of the Biginelli reaction is a series of bimolecular reactions leading to the desired dihydropyrimidinone.
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Sweet, F.; Fissekis, J. D. (1973). "Synthesis of 3,4-dihydro-2(1H)-pyrimidinones and the mechanism of the Biginelli reaction".
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Kumar, Atul; Maurya, Ram Awatar (2007). "An efficient bakers' yeast catalyzed synthesis of 3,4-dihydropyrimidin-2-(1H)-ones".
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by the amine onto the carbonyl group. This final step ensues a second condensation and results in the Biginelli compound.
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More recently products of the Biginelli reaction have been investigated as potential selective
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reported a modification to the Biginelli reaction that consistently generated higher yields.
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Kappe, C. Oliver (2005) "The Biginelli Reaction", in: J. Zhu and H. Bienaymé (eds.):
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Dihydropyrimidinones, the products of the Biginelli reaction, are widely used in the
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Kappe, C. O.; Stadler, A. (2004). "The Biginelli Dihydropyrimidine Synthesis".
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Kappe, C. O. (1993). "100 years of the biginelli dihydropyrimidine synthesis".
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protocols utilizing different linker combinations have been published.
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Zaugg, H. E.; Martin, W. B. (1965). "Α-Amidoalkylations at Carbon".
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antagonists. Including highly selective tricyclic compounds.
212:. The nucleophilic addition of urea gives the intermediate 122: 739: 344: 767: 432: 216:, which quickly dehydrates to give the desired product 196:
According to a mechanism proposed by Sweet in 1973 the
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This mechanism is superseded by one by Kappe in 1997:
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Erlenmeyer–Plöchl azlactone and amino-acid synthesis
3223:Divinylcyclopropane-cycloheptadiene rearrangement 471: 246: 4297: 155:such as copper(II) trifluoroacetate hydrate and 1016: 3483:Thermal rearrangement of aromatic hydrocarbons 2117:Thermal rearrangement of aromatic hydrocarbons 314:"Ueber Aldehyduramide des Acetessigäthers. II" 4212:Lectka enantioselective beta-lactam synthesis 1472: 1002: 311: 278: 3991:Inverse electron-demand Diels–Alder reaction 1812:Heterogeneous metal catalyzed cross-coupling 959:Panda, S.S.; Khanna, P.; Khanna, L. (2012). 564: 382: 3333:Lobry de Bruyn–Van Ekenstein transformation 929: 823: 1009: 995: 281:"Ueber Aldehyduramide des Acetessigäthers" 147:in 1891. The reaction can be catalyzed by 3823:Petrenko-Kritschenko piperidone synthesis 3278:Fritsch–Buttenberg–Wiechell rearrangement 961:"Biginelli Reaction: A Green Perspective" 914: 879: 672: 3986:Intramolecular Diels–Alder cycloaddition 475:Reaction Kinetics and Catalysis Letters 227:The mechanism of the Biginelli reaction 4331:Nitrogen heterocycle forming reactions 4298: 4006:Metal-centered cycloaddition reactions 3658:Debus–Radziszewski imidazole synthesis 1602:Bodroux–Chichibabin aldehyde synthesis 895:O'Reilly, B. C.; Atwal, K. S. (1987). 860:O'Reilly, B. C.; Atwal, K. S. (1987). 128:. It is named for the Italian chemist 4152:Diazoalkane 1,3-dipolar cycloaddition 4056:Vinylcyclopropane (5+2) cycloaddition 3961:Diazoalkane 1,3-dipolar cycloaddition 3733:Hurd–Mori 1,2,3-thiadiazole synthesis 3228:Dowd–Beckwith ring-expansion reaction 2395:Hurd–Mori 1,2,3-thiadiazole synthesis 1471: 1308:LFER solvent coefficients (data page) 990: 188: 95:that creates 3,4-dihydropyrimidin-2(1 4311:Carbon-carbon bond forming reactions 2963:Sharpless asymmetric dihydroxylation 2200:Methoxymethylenetriphenylphosphorane 3088:Allen–Millar–Trippett rearrangement 13: 4227:Nitrone-olefin (3+2) cycloaddition 4222:Niementowski quinazoline synthesis 4011:Nitrone-olefin (3+2) cycloaddition 3936:Azide-alkyne Huisgen cycloaddition 3798:Niementowski quinazoline synthesis 3553:Azide-alkyne Huisgen cycloaddition 2858:Meerwein–Ponndorf–Verley reduction 2410:Leimgruber–Batcho indole synthesis 405: 233: 222: 134: 14: 4342: 4051:Trimethylenemethane cycloaddition 3753:Johnson–Corey–Chaykovsky reaction 3618:Cadogan–Sundberg indole synthesis 3598:Bohlmann–Rahtz pyridine synthesis 3558:Baeyer–Emmerling indole synthesis 2365:Cadogan–Sundberg indole synthesis 1857:Johnson–Corey–Chaykovsky reaction 4147:Cook–Heilbron thiazole synthesis 3976:Hexadehydro Diels–Alder reaction 3803:Niementowski quinoline synthesis 3633:Cook–Heilbron thiazole synthesis 3578:Bischler–Möhlau indole synthesis 3488:Tiffeneau–Demjanov rearrangement 3118:Baker–Venkataraman rearrangement 2276:Horner–Wadsworth–Emmons reaction 1947:Mizoroki-Heck vs. Reductive Heck 1832:Horner–Wadsworth–Emmons reaction 1343:Neighbouring group participation 16:Multicomponent chemical reaction 3683:Fiesselmann thiophene synthesis 3513:Westphalen–LettrĂ© rearrangement 3493:Vinylcyclopropane rearrangement 3323:Kornblum–DeLaMare rearrangement 2968:Epoxidation of allylic alcohols 2878:Noyori asymmetric hydrogenation 2813:Kornblum–DeLaMare rearrangement 2488:Gallagher–Hollander degradation 952: 923: 888: 853: 817: 789: 761: 733: 689: 645:ACS Medicinal Chemistry Letters 631: 594: 558: 143:This reaction was developed by 4142:Chichibabin pyridine synthesis 3628:Chichibabin pyridine synthesis 3588:Blum–Ittah aziridine synthesis 3423:Ring expansion and contraction 1692:Cross dehydrogenative coupling 699:Journal of Medicinal Chemistry 530: 501: 465: 426: 376: 338: 305: 272: 247:Advances in Biginelli reaction 1: 4112:Bischler–Napieralski reaction 4070:Heterocycle forming reactions 3723:Hemetsberger indole synthesis 3583:Bischler–Napieralski reaction 3498:Wagner–Meerwein rearrangement 3468:Sommelet–Hauser rearrangement 3448:Seyferth–Gilbert homologation 3313:Ireland–Claisen rearrangement 3308:Hofmann–Martius rearrangement 3068:2,3-sigmatropic rearrangement 2683:Corey–Winter olefin synthesis 2608:Barton–McCombie deoxygenation 2251:Corey–Winter olefin synthesis 2205:Seyferth–Gilbert homologation 2072:Seyferth–Gilbert homologation 580:10.1016/S0960-894X(99)00572-7 399:10.1016/S0040-4020(01)87971-0 266: 208:leading to the carbenium ion 204:and the aryl aldehyde is the 178:, and alpha-1-a-antagonists. 4321:Multiple component reactions 4217:Lehmstedt–Tanasescu reaction 4177:Gabriel–Colman rearrangement 4132:Bucherer carbazole synthesis 4127:Borsche–Drechsel cyclization 4107:Bernthsen acridine synthesis 4092:Bamberger triazine synthesis 4077:Algar–Flynn–Oyamada reaction 3788:Nazarov cyclization reaction 3653:De Kimpe aziridine synthesis 3608:Bucherer carbazole synthesis 3603:Borsche–Drechsel cyclization 3373:Nazarov cyclization reaction 3353:Meyer–Schuster rearrangement 3283:Gabriel–Colman rearrangement 3033:Wolffenstein–Böters reaction 2918:Reduction of nitro compounds 2768:Grundmann aldehyde synthesis 2573:Algar–Flynn–Oyamada reaction 1982:Olefin conversion technology 1977:Nozaki–Hiyama–Kishi reaction 1772:Gabriel–Colman rearrangement 1662:Claisen-Schmidt condensation 1607:Bouveault aldehyde synthesis 946:10.1016/j.tetlet.2007.04.130 711:10.1021/acs.jmedchem.5b01586 552:10.1016/0040-4039(95)01660-A 238:Biginelli reaction mechanism 7: 4192:Hantzsch pyridine synthesis 3971:Enone–alkene cycloadditions 3793:Nenitzescu indole synthesis 3713:Hantzsch pyridine synthesis 3678:Ferrario–Ackermann reaction 3328:Kowalski ester homologation 3293:Halogen dance rearrangement 3138:Benzilic acid rearrangement 2563:Akabori amino-acid reaction 2523:Von Braun amide degradation 2468:Barbier–Wieland degradation 2420:Nenitzescu indole synthesis 2400:Kharasch–Sosnovsky reaction 2291:Julia–Kocienski olefination 2195:Kowalski ester homologation 1892:Kowalski ester homologation 1867:Julia–Kocienski olefination 1622:Cadiot–Chodkiewicz coupling 1547:Aza-Baylis–Hillman reaction 1492:Acetoacetic ester synthesis 1203:Dynamic binding (chemistry) 1193:Conrotatory and disrotatory 1168:Charge remote fragmentation 449:10.1002/0471264180.or063.01 360:10.1002/0471264180.or014.02 10: 4347: 4257:Robinson–Gabriel synthesis 4207:Kröhnke pyridine synthesis 4041:Retro-Diels–Alder reaction 3981:Imine Diels–Alder reaction 3768:Kröhnke pyridine synthesis 3383:Newman–Kwart rearrangement 3358:Mislow–Evans rearrangement 3268:Fischer–Hepp rearrangement 3213:Di-Ď€-methane rearrangement 2993:Stephen aldehyde synthesis 2728:Eschweiler–Clarke reaction 2445:Williamson ether synthesis 1762:Fujiwara–Moritani reaction 1667:Combes quinoline synthesis 1632:Carbonyl olefin metathesis 1333:More O'Ferrall–Jencks plot 1258:Grunwald–Winstein equation 1228:Electron-withdrawing group 1163:Catalytic resonance theory 978:10.2174/138527212799499859 4267:Urech hydantoin synthesis 4247:Pomeranz–Fritsch reaction 4172:Fischer oxazole synthesis 4069: 3906:1,3-Dipolar cycloaddition 3896: 3878:Urech hydantoin synthesis 3848:Reissert indole synthesis 3833:Pomeranz–Fritsch reaction 3763:Knorr quinoline synthesis 3693:Fischer oxazole synthesis 3623:Camps quinoline synthesis 3543:1,3-Dipolar cycloaddition 3531: 3443:Semipinacol rearrangement 3418:Ramberg–Bäcklund reaction 3403:Piancatelli rearrangement 3343:McFadyen–Stevens reaction 3098:Alpha-ketol rearrangement 3046: 2853:McFadyen–Stevens reaction 2798:Kiliani–Fischer synthesis 2718:Elbs persulfate oxidation 2643:Bouveault–Blanc reduction 2603:Baeyer–Villiger oxidation 2541: 2458: 2435:Schotten–Baumann reaction 2338: 2311:Ramberg–Bäcklund reaction 2218: 2190:Kiliani–Fischer synthesis 2170: 2032:Ramberg–Bäcklund reaction 2017:Pinacol coupling reaction 2012:Piancatelli rearrangement 1907:Liebeskind–Srogl coupling 1757:Fujimoto–Belleau reaction 1480: 1474:List of organic reactions 1338:Negative hyperconjugation 1083: 1025: 487:10.1007/s11144-008-5379-2 332:10.1002/cber.189102402126 299:10.1002/cber.189102401228 78: 52:Organic Chemistry Portal 46: 21: 4242:Pictet–Spengler reaction 4157:Einhorn–Brunner reaction 4122:Boger pyridine synthesis 4016:Oxo-Diels–Alder reaction 3931:Aza-Diels–Alder reaction 3828:Pictet–Spengler reaction 3728:Hofmann–Löffler reaction 3718:Hegedus indole synthesis 3688:Fischer indole synthesis 3563:Bartoli indole synthesis 3518:Willgerodt rearrangement 3348:McLafferty rearrangement 3258:Ferrier carbocyclization 3073:2,3-Wittig rearrangement 3063:1,2-Wittig rearrangement 2903:Parikh–Doering oxidation 2893:Oxygen rebound mechanism 2558:Adkins–Peterson reaction 2450:Yamaguchi esterification 2390:Hegedus indole synthesis 2355:Bartoli indole synthesis 2226:Bamford–Stevens reaction 2142:Weinreb ketone synthesis 2102:Stork enamine alkylation 1877:Knoevenagel condensation 1747:Ferrier carbocyclization 1637:Castro–Stephens coupling 1263:Hammett acidity function 1253:Free-energy relationship 1198:Curtin–Hammett principle 1183:Conformational isomerism 568:Bioorg. Med. Chem. Lett. 413:Multicomponent Reactions 4202:Knorr pyrrole synthesis 4137:Bucherer–Bergs reaction 4082:Allan–Robinson reaction 4061:Wagner-Jauregg reaction 3853:Ring-closing metathesis 3778:Larock indole synthesis 3758:Knorr pyrrole synthesis 3613:Bucherer–Bergs reaction 3478:Stieglitz rearrangement 3458:Skattebøl rearrangement 3428:Ring-closing metathesis 3288:Group transfer reaction 3253:Favorskii rearrangement 3193:Cornforth rearrangement 3123:Bamberger rearrangement 3028:Wolff–Kishner reduction 2848:Markó–Lam deoxygenation 2743:Fleming–Tamao oxidation 2738:Fischer–Tropsch process 2425:Oxymercuration reaction 2405:Knorr pyrrole synthesis 2231:Barton–Kellogg reaction 2137:Wagner-Jauregg reaction 2057:Ring-closing metathesis 2047:Reimer–Tiemann reaction 2037:Rauhut–Currier reaction 1952:Nef isocyanide reaction 1912:Malonic ester synthesis 1882:Knorr pyrrole synthesis 1817:High dilution principle 1752:Friedel–Crafts reaction 1687:Cross-coupling reaction 1612:Bucherer–Bergs reaction 1597:Blanc chloromethylation 1587:Blaise ketone synthesis 1562:Baylis–Hillman reaction 1557:Barton–Kellogg reaction 1532:Allan–Robinson reaction 1438:Woodward–Hoffmann rules 1173:Charge-transfer complex 415:, Wiley-VCH, Weinheim, 176:antihypertensive agents 4316:Condensation reactions 4306:Ring forming reactions 4167:Feist–Benary synthesis 3941:Bradsher cycloaddition 3911:4+4 Photocycloaddition 3868:Simmons–Smith reaction 3813:Paternò–BĂĽchi reaction 3673:Feist–Benary synthesis 3663:Dieckmann condensation 3413:Pummerer rearrangement 3393:Oxy-Cope rearrangement 3368:Myers allene synthesis 3318:Jacobsen rearrangement 3233:Electrocyclic reaction 3208:Demjanov rearrangement 3163:Buchner ring expansion 3133:Beckmann rearrangement 3113:Aza-Cope rearrangement 3108:Arndt–Eistert reaction 3083:Alkyne zipper reaction 3003:Transfer hydrogenation 2978:Sharpless oxyamination 2953:Selenoxide elimination 2838:Lombardo methylenation 2763:Griesbaum coozonolysis 2673:Corey–Itsuno reduction 2648:Boyland–Sims oxidation 2588:Angeli–Rimini reaction 2236:Boord olefin synthesis 2180:Arndt–Eistert reaction 2172:Homologation reactions 1972:Nitro-Mannich reaction 1887:Kolbe–Schmitt reaction 1697:Cross-coupling partner 1617:Buchner ring expansion 1537:Arndt–Eistert reaction 1303:Kinetic isotope effect 1050:Rearrangement reaction 916:10.3987/R-1987-05-1189 881:10.3987/R-1987-05-1185 312:Biginelli, P. (1891). 279:Biginelli, P. (1891). 239: 228: 183:Adenosine A2b receptor 140: 139:The Biginelli reaction 4026:Pauson–Khand reaction 3863:Sharpless epoxidation 3818:Pechmann condensation 3698:Friedländer synthesis 3648:Davis–Beirut reaction 3503:Wallach rearrangement 3473:Stevens rearrangement 3408:Pinacol rearrangement 3388:Overman rearrangement 3303:Hofmann rearrangement 3298:Hayashi rearrangement 3263:Ferrier rearrangement 3218:Dimroth rearrangement 3203:Curtius rearrangement 3198:Criegee rearrangement 3178:Claisen rearrangement 3168:Carroll rearrangement 3103:Amadori rearrangement 3093:Allylic rearrangement 2973:Sharpless epoxidation 2708:Dess–Martin oxidation 2633:Bohn–Schmidt reaction 2493:Hofmann rearrangement 2296:Kauffmann olefination 2219:Olefination reactions 2157:Wurtz–Fittig reaction 1992:Palladium–NHC complex 1872:Kauffmann olefination 1827:Homologation reaction 1677:Corey–House synthesis 1657:Claisen rearrangement 1453:Yukawa–Tsuno equation 1413:Swain–Lupton equation 1393:Spherical aromaticity 1328:Möbius–HĂĽckel concept 1113:Aromatic ring current 1075:Substitution reaction 263:green methodologies. 237: 226: 200:of ethylacetoacetate 138: 41:Ring forming reaction 4232:Paal–Knorr synthesis 4102:Barton–Zard reaction 4046:Staudinger synthesis 3996:Ketene cycloaddition 3966:Diels–Alder reaction 3946:Cheletropic reaction 3926:Alkyne trimerisation 3808:Paal–Knorr synthesis 3773:Kulinkovich reaction 3748:Jacobsen epoxidation 3668:Diels–Alder reaction 3463:Smiles rearrangement 3453:Sigmatropic reaction 3338:Lossen rearrangement 3188:Corey–Fuchs reaction 3153:Boekelheide reaction 3148:Bergmann degradation 3078:Achmatowicz reaction 2863:Methionine sulfoxide 2663:Clemmensen reduction 2623:Bergmann degradation 2553:Acyloin condensation 2518:Strecker degradation 2473:Bergmann degradation 2440:Ullmann condensation 2306:Peterson olefination 2281:Hydrazone iodination 2261:Elimination reaction 2162:Zincke–Suhl reaction 2082:Sonogashira coupling 2042:Reformatsky reaction 2002:Peterson olefination 1967:Nierenstein reaction 1897:Kulinkovich reaction 1712:Diels–Alder reaction 1672:Corey–Fuchs reaction 1652:Claisen condensation 1522:Alkyne trimerisation 1497:Acyloin condensation 1463:ÎŁ-bishomoaromaticity 1423:Thorpe–Ingold effect 1035:Elimination reaction 4252:Prilezhaev reaction 4237:Pellizzari reaction 3916:(4+3) cycloaddition 3883:Van Leusen reaction 3858:Robinson annulation 3843:Pschorr cyclization 3838:Prilezhaev reaction 3568:Bergman cyclization 3523:Wolff rearrangement 3508:Weerman degradation 3398:Pericyclic reaction 3378:Neber rearrangement 3273:Fries rearrangement 3158:Brook rearrangement 3143:Bergman cyclization 2988:Staudinger reaction 2933:Rosenmund reduction 2923:Reductive amination 2888:Oppenauer oxidation 2678:Corey–Kim oxidation 2653:Cannizzaro reaction 2528:Weerman degradation 2503:Isosaccharinic acid 2415:Mukaiyama hydration 2271:Hofmann elimination 2256:Dehydrohalogenation 2241:Chugaev elimination 2062:Robinson annulation 2007:Pfitzinger reaction 1777:Gattermann reaction 1722:Wulff–Dötz reaction 1702:Dakin–West reaction 1627:Carbonyl allylation 1572:Bergman cyclization 1358:Kennedy J. P. Orton 1278:Hammond's postulate 1248:Flippin–Lodge angle 1218:Electromeric effect 1143:Beta-silicon effect 1128:Baker–Nathan effect 933:Tetrahedron Letters 811:10.1021/ja01348a040 783:10.1021/ja00807a040 755:10.1021/ja01336a054 617:10.1021/jm00095a023 22:Biginelli reaction 4001:McCormack reaction 3951:Conia-ene reaction 3783:Madelung synthesis 3573:Biginelli reaction 3363:Mumm rearrangement 3248:Favorskii reaction 3183:Cope rearrangement 3173:Chan rearrangement 2938:Rubottom oxidation 2868:Miyaura borylation 2833:Lipid peroxidation 2828:Lindgren oxidation 2808:Kornblum oxidation 2803:Kolbe electrolysis 2748:Fukuyama reduction 2658:Carbonyl reduction 2508:Marker degradation 2370:Diazonium compound 2360:Boudouard reaction 2339:Carbon-heteroatom 2266:Grieco elimination 2052:Rieche formylation 1997:Passerini reaction 1927:Meerwein arylation 1847:Hydroxymethylation 1742:Favorskii reaction 1642:Chan rearrangement 1577:Biginelli reaction 1502:Aldol condensation 1348:2-Norbornyl cation 1323:Möbius aromaticity 1318:Markovnikov's rule 1213:Effective molarity 1158:BĂĽrgi–Dunitz angle 1148:Bicycloaromaticity 319:Chemische Berichte 286:Chemische Berichte 240: 229: 206:rate-limiting step 198:aldol condensation 189:Reaction mechanism 141: 105:ethyl acetoacetate 90:multiple-component 86:Biginelli reaction 57:biginelli-reaction 4293: 4292: 4289: 4288: 4285: 4284: 4277:Wohl–Aue reaction 3921:6+4 Cycloaddition 3738:Iodolactonization 3058:1,2-rearrangement 3023:Wohl–Aue reaction 2943:Sabatier reaction 2908:Pinnick oxidation 2873:Mozingo reduction 2818:Leuckart reaction 2773:Haloform reaction 2688:Criegee oxidation 2668:Collins oxidation 2618:Benkeser reaction 2613:Bechamp reduction 2583:Andrussow process 2568:Alcohol oxidation 2478:Edman degradation 2385:Haloform reaction 2334: 2333: 2321:Takai olefination 2286:Julia olefination 2112:Takai olefination 1987:Olefin metathesis 1862:Julia olefination 1787:Grignard reaction 1767:Fukuyama coupling 1682:Coupling reaction 1647:Chan–Lam coupling 1517:Alkyne metathesis 1512:Alkane metathesis 1368:Phosphaethynolate 1273:George S. Hammond 1233:Electronic effect 1188:Conjugated system 1070:Stereospecificity 1065:Stereoselectivity 1030:Addition reaction 1019:organic reactions 839:10.1021/jo971010u 833:(21): 7201–7204. 799:J. Am. Chem. Soc. 777:(26): 8741–8749. 771:J. Am. Chem. Soc. 743:J. Am. Chem. Soc. 657:10.1021/ml400185v 651:(11): 1031–1036. 611:(17): 3254–3263. 546:(43): 7819–7822. 540:Tetrahedron Lett. 524:10.1021/jo970846u 436:Organic Reactions 421:978-3-527-30806-4 393:(32): 6937–6963. 157:boron trifluoride 93:chemical reaction 82: 81: 4338: 4272:Wenker synthesis 4262:StollĂ© synthesis 4117:Bobbitt reaction 4087:Auwers synthesis 4031:Povarov reaction 3956:Cyclopropanation 3894: 3893: 3888:Wenker synthesis 3643:Darzens reaction 3593:Bobbitt reaction 3438:Schmidt reaction 3243:Enyne metathesis 3018:Whiting reaction 3013:Wharton reaction 2958:Shapiro reaction 2948:Sarett oxidation 2913:PrĂ©vost reaction 2723:Emde degradation 2533:Wohl degradation 2513:Ruff degradation 2483:Emde degradation 2380:Grignard reagent 2316:Shapiro reaction 2301:McMurry reaction 2168: 2167: 2132:Ullmann reaction 2097:StollĂ© synthesis 2087:Stetter reaction 2077:Shapiro reaction 2067:Sakurai reaction 1962:Negishi coupling 1942:Minisci reaction 1937:Michael reaction 1922:McMurry reaction 1917:Mannich reaction 1797:Hammick reaction 1792:Grignard reagent 1732:Enyne metathesis 1717:Doebner reaction 1707:Darzens reaction 1552:Barbier reaction 1542:Auwers synthesis 1469: 1468: 1443:Woodward's rules 1408:Superaromaticity 1398:Spiroaromaticity 1298:Inductive effect 1293:Hyperconjugation 1268:Hammett equation 1208:Edwards equation 1060:Regioselectivity 1011: 1004: 997: 988: 987: 982: 981: 966:Curr. Org. Chem. 956: 950: 949: 927: 921: 920: 918: 909:(5): 1189–1192. 892: 886: 885: 883: 874:(5): 1185–1188. 857: 851: 850: 821: 815: 814: 805:(9): 3751–3758. 793: 787: 786: 765: 759: 758: 749:(9): 3784–3791. 737: 731: 730: 705:(5): 1967–1983. 693: 687: 686: 676: 635: 629: 628: 598: 592: 591: 562: 556: 555: 534: 528: 527: 505: 499: 498: 469: 463: 462: 430: 424: 409: 403: 402: 380: 374: 373: 342: 336: 335: 326:(2): 2962–2967. 309: 303: 302: 276: 145:Pietro Biginelli 130:Pietro Biginelli 74: 59: 31:Pietro Biginelli 19: 18: 4346: 4345: 4341: 4340: 4339: 4337: 4336: 4335: 4296: 4295: 4294: 4281: 4182:Gewald reaction 4065: 3892: 3873:Skraup reaction 3708:Graham reaction 3703:Gewald reaction 3534: 3527: 3049: 3042: 2998:Swern oxidation 2983:Stahl oxidation 2928:Riley oxidation 2883:Omega oxidation 2843:Luche reduction 2793:Jones oxidation 2758:Glycol cleavage 2753:Ganem oxidation 2698:Davis oxidation 2693:Dakin oxidation 2628:Birch reduction 2578:Amide reduction 2544: 2537: 2498:Hooker reaction 2460: 2454: 2342: 2340: 2330: 2326:Wittig reaction 2214: 2210:Wittig reaction 2185:Hooker reaction 2166: 2147:Wittig reaction 2122:Thorpe reaction 2107:Suzuki reaction 2092:Stille reaction 2027:Quelet reaction 1902:Kumada coupling 1852:Ivanov reaction 1842:Hydrovinylation 1822:Hiyama coupling 1782:Glaser coupling 1592:Blaise reaction 1582:Bingel reaction 1567:Benary reaction 1484: 1482: 1476: 1467: 1363:Passive binding 1283:Homoaromaticity 1133:Baldwin's rules 1108:Antiaromaticity 1103:Anomeric effect 1079: 1021: 1015: 985: 957: 953: 928: 924: 893: 889: 858: 854: 822: 818: 794: 790: 766: 762: 738: 734: 694: 690: 636: 632: 599: 595: 563: 559: 535: 531: 506: 502: 470: 466: 459: 431: 427: 410: 406: 381: 377: 370: 343: 339: 310: 306: 277: 273: 269: 251:In 1987, Atwal 249: 191: 172:calcium channel 70: 55: 17: 12: 11: 5: 4344: 4334: 4333: 4328: 4326:Name reactions 4323: 4318: 4313: 4308: 4291: 4290: 4287: 4286: 4283: 4282: 4280: 4279: 4274: 4269: 4264: 4259: 4254: 4249: 4244: 4239: 4234: 4229: 4224: 4219: 4214: 4209: 4204: 4199: 4194: 4189: 4187:Hantzsch ester 4184: 4179: 4174: 4169: 4164: 4159: 4154: 4149: 4144: 4139: 4134: 4129: 4124: 4119: 4114: 4109: 4104: 4099: 4097:Banert cascade 4094: 4089: 4084: 4079: 4073: 4071: 4067: 4066: 4064: 4063: 4058: 4053: 4048: 4043: 4038: 4036:Prato reaction 4033: 4028: 4023: 4018: 4013: 4008: 4003: 3998: 3993: 3988: 3983: 3978: 3973: 3968: 3963: 3958: 3953: 3948: 3943: 3938: 3933: 3928: 3923: 3918: 3913: 3908: 3902: 3900: 3891: 3890: 3885: 3880: 3875: 3870: 3865: 3860: 3855: 3850: 3845: 3840: 3835: 3830: 3825: 3820: 3815: 3810: 3805: 3800: 3795: 3790: 3785: 3780: 3775: 3770: 3765: 3760: 3755: 3750: 3745: 3740: 3735: 3730: 3725: 3720: 3715: 3710: 3705: 3700: 3695: 3690: 3685: 3680: 3675: 3670: 3665: 3660: 3655: 3650: 3645: 3640: 3635: 3630: 3625: 3620: 3615: 3610: 3605: 3600: 3595: 3590: 3585: 3580: 3575: 3570: 3565: 3560: 3555: 3550: 3545: 3539: 3537: 3529: 3528: 3526: 3525: 3520: 3515: 3510: 3505: 3500: 3495: 3490: 3485: 3480: 3475: 3470: 3465: 3460: 3455: 3450: 3445: 3440: 3435: 3430: 3425: 3420: 3415: 3410: 3405: 3400: 3395: 3390: 3385: 3380: 3375: 3370: 3365: 3360: 3355: 3350: 3345: 3340: 3335: 3330: 3325: 3320: 3315: 3310: 3305: 3300: 3295: 3290: 3285: 3280: 3275: 3270: 3265: 3260: 3255: 3250: 3245: 3240: 3235: 3230: 3225: 3220: 3215: 3210: 3205: 3200: 3195: 3190: 3185: 3180: 3175: 3170: 3165: 3160: 3155: 3150: 3145: 3140: 3135: 3130: 3128:Banert cascade 3125: 3120: 3115: 3110: 3105: 3100: 3095: 3090: 3085: 3080: 3075: 3070: 3065: 3060: 3054: 3052: 3048:Rearrangement 3044: 3043: 3041: 3040: 3038:Zinin reaction 3035: 3030: 3025: 3020: 3015: 3010: 3008:Wacker process 3005: 3000: 2995: 2990: 2985: 2980: 2975: 2970: 2965: 2960: 2955: 2950: 2945: 2940: 2935: 2930: 2925: 2920: 2915: 2910: 2905: 2900: 2895: 2890: 2885: 2880: 2875: 2870: 2865: 2860: 2855: 2850: 2845: 2840: 2835: 2830: 2825: 2820: 2815: 2810: 2805: 2800: 2795: 2790: 2785: 2783:Hydrogenolysis 2780: 2775: 2770: 2765: 2760: 2755: 2750: 2745: 2740: 2735: 2733:Étard reaction 2730: 2725: 2720: 2715: 2710: 2705: 2700: 2695: 2690: 2685: 2680: 2675: 2670: 2665: 2660: 2655: 2650: 2645: 2640: 2638:Bosch reaction 2635: 2630: 2625: 2620: 2615: 2610: 2605: 2600: 2595: 2590: 2585: 2580: 2575: 2570: 2565: 2560: 2555: 2549: 2547: 2543:Organic redox 2539: 2538: 2536: 2535: 2530: 2525: 2520: 2515: 2510: 2505: 2500: 2495: 2490: 2485: 2480: 2475: 2470: 2464: 2462: 2456: 2455: 2453: 2452: 2447: 2442: 2437: 2432: 2427: 2422: 2417: 2412: 2407: 2402: 2397: 2392: 2387: 2382: 2377: 2375:Esterification 2372: 2367: 2362: 2357: 2352: 2346: 2344: 2336: 2335: 2332: 2331: 2329: 2328: 2323: 2318: 2313: 2308: 2303: 2298: 2293: 2288: 2283: 2278: 2273: 2268: 2263: 2258: 2253: 2248: 2243: 2238: 2233: 2228: 2222: 2220: 2216: 2215: 2213: 2212: 2207: 2202: 2197: 2192: 2187: 2182: 2176: 2174: 2165: 2164: 2159: 2154: 2152:Wurtz reaction 2149: 2144: 2139: 2134: 2129: 2124: 2119: 2114: 2109: 2104: 2099: 2094: 2089: 2084: 2079: 2074: 2069: 2064: 2059: 2054: 2049: 2044: 2039: 2034: 2029: 2024: 2022:Prins reaction 2019: 2014: 2009: 2004: 1999: 1994: 1989: 1984: 1979: 1974: 1969: 1964: 1959: 1954: 1949: 1944: 1939: 1934: 1929: 1924: 1919: 1914: 1909: 1904: 1899: 1894: 1889: 1884: 1879: 1874: 1869: 1864: 1859: 1854: 1849: 1844: 1839: 1837:Hydrocyanation 1834: 1829: 1824: 1819: 1814: 1809: 1807:Henry reaction 1804: 1799: 1794: 1789: 1784: 1779: 1774: 1769: 1764: 1759: 1754: 1749: 1744: 1739: 1734: 1729: 1724: 1719: 1714: 1709: 1704: 1699: 1694: 1689: 1684: 1679: 1674: 1669: 1664: 1659: 1654: 1649: 1644: 1639: 1634: 1629: 1624: 1619: 1614: 1609: 1604: 1599: 1594: 1589: 1584: 1579: 1574: 1569: 1564: 1559: 1554: 1549: 1544: 1539: 1534: 1529: 1524: 1519: 1514: 1509: 1507:Aldol reaction 1504: 1499: 1494: 1488: 1486: 1481:Carbon-carbon 1478: 1477: 1466: 1465: 1460: 1458:Zaitsev's rule 1455: 1450: 1445: 1440: 1435: 1430: 1425: 1420: 1415: 1410: 1405: 1403:Steric effects 1400: 1395: 1390: 1385: 1380: 1375: 1370: 1365: 1360: 1355: 1350: 1345: 1340: 1335: 1330: 1325: 1320: 1315: 1310: 1305: 1300: 1295: 1290: 1285: 1280: 1275: 1270: 1265: 1260: 1255: 1250: 1245: 1240: 1235: 1230: 1225: 1220: 1215: 1210: 1205: 1200: 1195: 1190: 1185: 1180: 1175: 1170: 1165: 1160: 1155: 1150: 1145: 1140: 1135: 1130: 1125: 1120: 1115: 1110: 1105: 1100: 1095: 1090: 1084: 1081: 1080: 1078: 1077: 1072: 1067: 1062: 1057: 1055:Redox reaction 1052: 1047: 1042: 1040:Polymerization 1037: 1032: 1026: 1023: 1022: 1014: 1013: 1006: 999: 991: 984: 983: 972:(4): 507–520. 951: 922: 887: 852: 816: 788: 760: 732: 688: 630: 593: 557: 529: 500: 464: 457: 425: 404: 375: 368: 337: 304: 270: 268: 265: 248: 245: 190: 187: 168:pharmaceutical 149:Brønsted acids 80: 79: 76: 75: 68: 61: 60: 53: 49: 48: 44: 43: 38: 37:Reaction type 34: 33: 28: 24: 23: 15: 9: 6: 4: 3: 2: 4343: 4332: 4329: 4327: 4324: 4322: 4319: 4317: 4314: 4312: 4309: 4307: 4304: 4303: 4301: 4278: 4275: 4273: 4270: 4268: 4265: 4263: 4260: 4258: 4255: 4253: 4250: 4248: 4245: 4243: 4240: 4238: 4235: 4233: 4230: 4228: 4225: 4223: 4220: 4218: 4215: 4213: 4210: 4208: 4205: 4203: 4200: 4198: 4197:Herz reaction 4195: 4193: 4190: 4188: 4185: 4183: 4180: 4178: 4175: 4173: 4170: 4168: 4165: 4163: 4160: 4158: 4155: 4153: 4150: 4148: 4145: 4143: 4140: 4138: 4135: 4133: 4130: 4128: 4125: 4123: 4120: 4118: 4115: 4113: 4110: 4108: 4105: 4103: 4100: 4098: 4095: 4093: 4090: 4088: 4085: 4083: 4080: 4078: 4075: 4074: 4072: 4068: 4062: 4059: 4057: 4054: 4052: 4049: 4047: 4044: 4042: 4039: 4037: 4034: 4032: 4029: 4027: 4024: 4022: 4019: 4017: 4014: 4012: 4009: 4007: 4004: 4002: 3999: 3997: 3994: 3992: 3989: 3987: 3984: 3982: 3979: 3977: 3974: 3972: 3969: 3967: 3964: 3962: 3959: 3957: 3954: 3952: 3949: 3947: 3944: 3942: 3939: 3937: 3934: 3932: 3929: 3927: 3924: 3922: 3919: 3917: 3914: 3912: 3909: 3907: 3904: 3903: 3901: 3899: 3898:Cycloaddition 3895: 3889: 3886: 3884: 3881: 3879: 3876: 3874: 3871: 3869: 3866: 3864: 3861: 3859: 3856: 3854: 3851: 3849: 3846: 3844: 3841: 3839: 3836: 3834: 3831: 3829: 3826: 3824: 3821: 3819: 3816: 3814: 3811: 3809: 3806: 3804: 3801: 3799: 3796: 3794: 3791: 3789: 3786: 3784: 3781: 3779: 3776: 3774: 3771: 3769: 3766: 3764: 3761: 3759: 3756: 3754: 3751: 3749: 3746: 3744: 3743:Isay reaction 3741: 3739: 3736: 3734: 3731: 3729: 3726: 3724: 3721: 3719: 3716: 3714: 3711: 3709: 3706: 3704: 3701: 3699: 3696: 3694: 3691: 3689: 3686: 3684: 3681: 3679: 3676: 3674: 3671: 3669: 3666: 3664: 3661: 3659: 3656: 3654: 3651: 3649: 3646: 3644: 3641: 3639: 3638:Cycloaddition 3636: 3634: 3631: 3629: 3626: 3624: 3621: 3619: 3616: 3614: 3611: 3609: 3606: 3604: 3601: 3599: 3596: 3594: 3591: 3589: 3586: 3584: 3581: 3579: 3576: 3574: 3571: 3569: 3566: 3564: 3561: 3559: 3556: 3554: 3551: 3549: 3546: 3544: 3541: 3540: 3538: 3536: 3533:Ring forming 3530: 3524: 3521: 3519: 3516: 3514: 3511: 3509: 3506: 3504: 3501: 3499: 3496: 3494: 3491: 3489: 3486: 3484: 3481: 3479: 3476: 3474: 3471: 3469: 3466: 3464: 3461: 3459: 3456: 3454: 3451: 3449: 3446: 3444: 3441: 3439: 3436: 3434: 3433:Rupe reaction 3431: 3429: 3426: 3424: 3421: 3419: 3416: 3414: 3411: 3409: 3406: 3404: 3401: 3399: 3396: 3394: 3391: 3389: 3386: 3384: 3381: 3379: 3376: 3374: 3371: 3369: 3366: 3364: 3361: 3359: 3356: 3354: 3351: 3349: 3346: 3344: 3341: 3339: 3336: 3334: 3331: 3329: 3326: 3324: 3321: 3319: 3316: 3314: 3311: 3309: 3306: 3304: 3301: 3299: 3296: 3294: 3291: 3289: 3286: 3284: 3281: 3279: 3276: 3274: 3271: 3269: 3266: 3264: 3261: 3259: 3256: 3254: 3251: 3249: 3246: 3244: 3241: 3239: 3236: 3234: 3231: 3229: 3226: 3224: 3221: 3219: 3216: 3214: 3211: 3209: 3206: 3204: 3201: 3199: 3196: 3194: 3191: 3189: 3186: 3184: 3181: 3179: 3176: 3174: 3171: 3169: 3166: 3164: 3161: 3159: 3156: 3154: 3151: 3149: 3146: 3144: 3141: 3139: 3136: 3134: 3131: 3129: 3126: 3124: 3121: 3119: 3116: 3114: 3111: 3109: 3106: 3104: 3101: 3099: 3096: 3094: 3091: 3089: 3086: 3084: 3081: 3079: 3076: 3074: 3071: 3069: 3066: 3064: 3061: 3059: 3056: 3055: 3053: 3051: 3045: 3039: 3036: 3034: 3031: 3029: 3026: 3024: 3021: 3019: 3016: 3014: 3011: 3009: 3006: 3004: 3001: 2999: 2996: 2994: 2991: 2989: 2986: 2984: 2981: 2979: 2976: 2974: 2971: 2969: 2966: 2964: 2961: 2959: 2956: 2954: 2951: 2949: 2946: 2944: 2941: 2939: 2936: 2934: 2931: 2929: 2926: 2924: 2921: 2919: 2916: 2914: 2911: 2909: 2906: 2904: 2901: 2899: 2896: 2894: 2891: 2889: 2886: 2884: 2881: 2879: 2876: 2874: 2871: 2869: 2866: 2864: 2861: 2859: 2856: 2854: 2851: 2849: 2846: 2844: 2841: 2839: 2836: 2834: 2831: 2829: 2826: 2824: 2823:Ley oxidation 2821: 2819: 2816: 2814: 2811: 2809: 2806: 2804: 2801: 2799: 2796: 2794: 2791: 2789: 2788:Hydroxylation 2786: 2784: 2781: 2779: 2778:Hydrogenation 2776: 2774: 2771: 2769: 2766: 2764: 2761: 2759: 2756: 2754: 2751: 2749: 2746: 2744: 2741: 2739: 2736: 2734: 2731: 2729: 2726: 2724: 2721: 2719: 2716: 2714: 2713:DNA oxidation 2711: 2709: 2706: 2704: 2703:Deoxygenation 2701: 2699: 2696: 2694: 2691: 2689: 2686: 2684: 2681: 2679: 2676: 2674: 2671: 2669: 2666: 2664: 2661: 2659: 2656: 2654: 2651: 2649: 2646: 2644: 2641: 2639: 2636: 2634: 2631: 2629: 2626: 2624: 2621: 2619: 2616: 2614: 2611: 2609: 2606: 2604: 2601: 2599: 2596: 2594: 2593:Aromatization 2591: 2589: 2586: 2584: 2581: 2579: 2576: 2574: 2571: 2569: 2566: 2564: 2561: 2559: 2556: 2554: 2551: 2550: 2548: 2546: 2540: 2534: 2531: 2529: 2526: 2524: 2521: 2519: 2516: 2514: 2511: 2509: 2506: 2504: 2501: 2499: 2496: 2494: 2491: 2489: 2486: 2484: 2481: 2479: 2476: 2474: 2471: 2469: 2466: 2465: 2463: 2457: 2451: 2448: 2446: 2443: 2441: 2438: 2436: 2433: 2431: 2430:Reed reaction 2428: 2426: 2423: 2421: 2418: 2416: 2413: 2411: 2408: 2406: 2403: 2401: 2398: 2396: 2393: 2391: 2388: 2386: 2383: 2381: 2378: 2376: 2373: 2371: 2368: 2366: 2363: 2361: 2358: 2356: 2353: 2351: 2348: 2347: 2345: 2341:bond forming 2337: 2327: 2324: 2322: 2319: 2317: 2314: 2312: 2309: 2307: 2304: 2302: 2299: 2297: 2294: 2292: 2289: 2287: 2284: 2282: 2279: 2277: 2274: 2272: 2269: 2267: 2264: 2262: 2259: 2257: 2254: 2252: 2249: 2247: 2246:Cope reaction 2244: 2242: 2239: 2237: 2234: 2232: 2229: 2227: 2224: 2223: 2221: 2217: 2211: 2208: 2206: 2203: 2201: 2198: 2196: 2193: 2191: 2188: 2186: 2183: 2181: 2178: 2177: 2175: 2173: 2169: 2163: 2160: 2158: 2155: 2153: 2150: 2148: 2145: 2143: 2140: 2138: 2135: 2133: 2130: 2128: 2125: 2123: 2120: 2118: 2115: 2113: 2110: 2108: 2105: 2103: 2100: 2098: 2095: 2093: 2090: 2088: 2085: 2083: 2080: 2078: 2075: 2073: 2070: 2068: 2065: 2063: 2060: 2058: 2055: 2053: 2050: 2048: 2045: 2043: 2040: 2038: 2035: 2033: 2030: 2028: 2025: 2023: 2020: 2018: 2015: 2013: 2010: 2008: 2005: 2003: 2000: 1998: 1995: 1993: 1990: 1988: 1985: 1983: 1980: 1978: 1975: 1973: 1970: 1968: 1965: 1963: 1960: 1958: 1957:Nef synthesis 1955: 1953: 1950: 1948: 1945: 1943: 1940: 1938: 1935: 1933: 1932:Methylenation 1930: 1928: 1925: 1923: 1920: 1918: 1915: 1913: 1910: 1908: 1905: 1903: 1900: 1898: 1895: 1893: 1890: 1888: 1885: 1883: 1880: 1878: 1875: 1873: 1870: 1868: 1865: 1863: 1860: 1858: 1855: 1853: 1850: 1848: 1845: 1843: 1840: 1838: 1835: 1833: 1830: 1828: 1825: 1823: 1820: 1818: 1815: 1813: 1810: 1808: 1805: 1803: 1802:Heck reaction 1800: 1798: 1795: 1793: 1790: 1788: 1785: 1783: 1780: 1778: 1775: 1773: 1770: 1768: 1765: 1763: 1760: 1758: 1755: 1753: 1750: 1748: 1745: 1743: 1740: 1738: 1735: 1733: 1730: 1728: 1725: 1723: 1720: 1718: 1715: 1713: 1710: 1708: 1705: 1703: 1700: 1698: 1695: 1693: 1690: 1688: 1685: 1683: 1680: 1678: 1675: 1673: 1670: 1668: 1665: 1663: 1660: 1658: 1655: 1653: 1650: 1648: 1645: 1643: 1640: 1638: 1635: 1633: 1630: 1628: 1625: 1623: 1620: 1618: 1615: 1613: 1610: 1608: 1605: 1603: 1600: 1598: 1595: 1593: 1590: 1588: 1585: 1583: 1580: 1578: 1575: 1573: 1570: 1568: 1565: 1563: 1560: 1558: 1555: 1553: 1550: 1548: 1545: 1543: 1540: 1538: 1535: 1533: 1530: 1528: 1525: 1523: 1520: 1518: 1515: 1513: 1510: 1508: 1505: 1503: 1500: 1498: 1495: 1493: 1490: 1489: 1487: 1483:bond forming 1479: 1475: 1470: 1464: 1461: 1459: 1456: 1454: 1451: 1449: 1448:Y-aromaticity 1446: 1444: 1441: 1439: 1436: 1434: 1433:Walsh diagram 1431: 1429: 1426: 1424: 1421: 1419: 1418:Taft equation 1416: 1414: 1411: 1409: 1406: 1404: 1401: 1399: 1396: 1394: 1391: 1389: 1388:ÎŁ-aromaticity 1386: 1384: 1381: 1379: 1376: 1374: 1371: 1369: 1366: 1364: 1361: 1359: 1356: 1354: 1351: 1349: 1346: 1344: 1341: 1339: 1336: 1334: 1331: 1329: 1326: 1324: 1321: 1319: 1316: 1314: 1313:Marcus theory 1311: 1309: 1306: 1304: 1301: 1299: 1296: 1294: 1291: 1289: 1288:HĂĽckel's rule 1286: 1284: 1281: 1279: 1276: 1274: 1271: 1269: 1266: 1264: 1261: 1259: 1256: 1254: 1251: 1249: 1246: 1244: 1243:Evelyn effect 1241: 1239: 1236: 1234: 1231: 1229: 1226: 1224: 1223:Electron-rich 1221: 1219: 1216: 1214: 1211: 1209: 1206: 1204: 1201: 1199: 1196: 1194: 1191: 1189: 1186: 1184: 1181: 1179: 1176: 1174: 1171: 1169: 1166: 1164: 1161: 1159: 1156: 1154: 1151: 1149: 1146: 1144: 1141: 1139: 1138:Bema Hapothle 1136: 1134: 1131: 1129: 1126: 1124: 1121: 1119: 1116: 1114: 1111: 1109: 1106: 1104: 1101: 1099: 1096: 1094: 1091: 1089: 1086: 1085: 1082: 1076: 1073: 1071: 1068: 1066: 1063: 1061: 1058: 1056: 1053: 1051: 1048: 1046: 1043: 1041: 1038: 1036: 1033: 1031: 1028: 1027: 1024: 1020: 1012: 1007: 1005: 1000: 998: 993: 992: 989: 979: 975: 971: 968: 967: 962: 955: 947: 943: 939: 935: 934: 926: 917: 912: 908: 904: 903: 898: 891: 882: 877: 873: 869: 868: 863: 856: 848: 844: 840: 836: 832: 829: 828: 827:J. Org. Chem. 820: 812: 808: 804: 801: 800: 792: 784: 780: 776: 773: 772: 764: 756: 752: 748: 745: 744: 736: 728: 724: 720: 716: 712: 708: 704: 700: 692: 684: 680: 675: 670: 666: 662: 658: 654: 650: 646: 642: 634: 626: 622: 618: 614: 610: 607: 606: 605:J. Med. Chem. 597: 589: 585: 581: 577: 573: 570: 569: 561: 553: 549: 545: 542: 541: 533: 525: 521: 517: 514: 513: 512:J. Org. Chem. 504: 496: 492: 488: 484: 480: 476: 468: 460: 454: 450: 446: 442: 438: 437: 429: 422: 418: 414: 408: 400: 396: 392: 388: 387: 379: 371: 365: 361: 357: 353: 350: 349: 341: 333: 329: 325: 321: 320: 315: 308: 300: 296: 293:: 1317–1319. 292: 288: 287: 282: 275: 271: 264: 262: 258: 254: 244: 236: 232: 225: 221: 219: 215: 211: 207: 203: 199: 194: 186: 184: 179: 177: 173: 169: 164: 162: 158: 154: 150: 146: 137: 133: 131: 127: 124: 120: 117: 113: 109: 106: 102: 98: 94: 91: 87: 77: 73: 69: 66: 63: 62: 58: 54: 51: 50: 45: 42: 39: 36: 35: 32: 29: 26: 25: 20: 3572: 3238:Ene reaction 2598:Autoxidation 2459:Degradation 2350:Azo coupling 2127:Ugi reaction 1727:Ene reaction 1576: 1527:Alkynylation 1378:Polyfluorene 1373:Polar effect 1238:Electrophile 1153:Bredt's rule 1123:Baird's rule 1093:Alpha effect 969: 964: 954: 940:(26): 4569. 937: 931: 925: 906: 902:Heterocycles 900: 890: 871: 867:Heterocycles 865: 855: 830: 825: 819: 802: 797: 791: 774: 769: 763: 746: 741: 735: 702: 698: 691: 648: 644: 633: 608: 603: 596: 574:(1): 49–51. 571: 566: 560: 543: 538: 532: 518:(10): 3454. 515: 510: 503: 478: 474: 467: 440: 434: 428: 412: 407: 390: 384: 378: 351: 346: 340: 323: 317: 307: 290: 284: 274: 260: 252: 250: 241: 230: 217: 213: 209: 201: 195: 192: 180: 170:industry as 165: 142: 125: 118: 116:benzaldehyde 107: 100: 96: 85: 83: 72:RXNO:0000236 67:ontology ID 47:Identifiers 27:Named after 1737:Ethenolysis 1383:Ring strain 1353:Nucleophile 1178:Clar's rule 1118:Aromaticity 386:Tetrahedron 348:Org. React. 161:solid-phase 153:Lewis acids 4300:Categories 4021:Ozonolysis 3548:Annulation 2898:Ozonolysis 1017:Topics in 481:(2): 385. 458:0471264180 369:0471264180 267:References 257:Atul Kumar 174:blockers, 159:. Several 151:and/or by 110:, an aryl 3535:reactions 3050:reactions 2545:reactions 2461:reactions 2343:reactions 1485:reactions 719:0022-2623 665:1948-5875 443:: 1–116. 114:(such as 1428:Vinylogy 1098:Annulene 1045:Reagents 847:11671828 727:26824742 683:24900602 588:10636241 495:93287161 112:aldehyde 1088:A value 674:4027370 625:1387168 121:), and 99:)-ones 845:  725:  717:  681:  671:  663:  623:  586:  493:  455:  419:  366:  354:: 88. 253:et al. 491:S2CID 103:from 88:is a 843:PMID 723:PMID 715:ISSN 679:PMID 661:ISSN 621:PMID 584:PMID 453:ISBN 417:ISBN 364:ISBN 123:urea 84:The 974:doi 942:doi 911:doi 876:doi 835:doi 807:doi 779:doi 751:doi 707:doi 669:PMC 653:doi 613:doi 576:doi 548:doi 520:doi 483:doi 445:doi 395:doi 356:doi 328:doi 295:doi 261:via 65:RSC 4302:: 970:16 963:. 938:48 936:. 907:26 905:. 899:. 872:26 870:. 864:. 841:. 831:62 803:54 775:95 747:55 721:. 713:. 703:59 701:. 677:. 667:. 659:. 647:. 643:. 619:. 609:35 582:. 572:10 544:36 516:63 489:. 479:95 477:. 451:. 441:63 439:. 391:49 389:. 362:. 352:14 324:24 322:. 316:. 291:24 289:. 283:. 220:. 132:. 1010:e 1003:t 996:v 980:. 976:: 948:. 944:: 919:. 913:: 884:. 878:: 849:. 837:: 813:. 809:: 785:. 781:: 757:. 753:: 729:. 709:: 685:. 655:: 649:4 627:. 615:: 590:. 578:: 554:. 550:: 526:. 522:: 497:. 485:: 461:. 447:: 423:. 401:. 397:: 372:. 358:: 334:. 330:: 301:. 297:: 218:5 214:4 210:2 202:1 126:3 119:2 108:1 101:4 97:H

Index

Pietro Biginelli
Ring forming reaction
biginelli-reaction
RSC
RXNO:0000236
multiple-component
chemical reaction
ethyl acetoacetate
aldehyde
benzaldehyde
urea
Pietro Biginelli
The Biginelli reaction
Pietro Biginelli
Brønsted acids
Lewis acids
boron trifluoride
solid-phase
pharmaceutical
calcium channel
antihypertensive agents
Adenosine A2b receptor
aldol condensation
rate-limiting step
The mechanism of the Biginelli reaction
Biginelli reaction mechanism
Atul Kumar
"Ueber Aldehyduramide des Acetessigäthers"
Chemische Berichte
doi

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