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Kostanecki acylation

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94: 56: 253:"3-Benzoylquinoxalin-2(1H)-one in the Kostanecki-Robinson Reaction. Synthesis and Structure of 2-Oxo-4-phenylpyrano[2,3-b]quinoxaline" 134: 129: 314: 309: 251:
Mamedov, V. A.; Kalinin, A. A.; Gubaidullin, A. T.; Litvinov, I. A.; Levin, Ya. A. (2003).
8: 319: 293:, Weissberger, A. and Taylor, E. C., eds.; Wiley & Sons: New York, vol. 31, p. 495. 272: 79: 155: 175: 37: 21: 276: 264: 252: 233: 202: 167: 41: 291:
Chromenes, Chromanones, and Chromones from The Chemistry of Heterocyclic Compounds
93: 36:-hydroxyaryl ketones with aliphatic acid anhydrides, followed by cyclization. If 268: 303: 237: 179: 154:
Gaspar, A.; Matos, M. J. O.; Garrido, J.; Uriarte, E.; Borges, F. (2014).
206: 55: 171: 117: 112: 106: 29: 221: 86: 45: 25: 250: 193:
Sethna, S. M.; Shah, N. M. (1945). "The Chemistry of Coumarins".
49: 67:
The mechanism consists of three well-differentiated reactions:
153: 75:-acylation with formation of a tetrahedral intermediate 219: 156:"Chromone: A Valid Scaffold in Medicinal Chemistry" 301: 222:"Ueber eine Bildungsweise von Chromonderivaten" 82:to cyclize and to form a hydroxydihydrochromone 226:Berichte der Deutschen Chemischen Gesellschaft 192: 220:v. Kostanecki, St.; Różycki, A. (1901). 89:group to form the chromone (or coumarin) 302: 257:Chemistry of Heterocyclic Compounds 13: 92: 54: 14: 331: 135:Baker–Venkataraman rearrangement 44:) is used, a particular type of 283: 244: 213: 186: 147: 1: 140: 62: 7: 123: 100: 10: 336: 238:10.1002/cber.19010340119 269:10.1023/A:1023028927007 130:Allan–Robinson reaction 97: 59: 96: 58: 289:Ellis, G. P. (1977) 20:is a method used in 18:Kostanecki acylation 207:10.1021/cr60113a001 85:Elimination of the 98: 80:aldol condensation 60: 315:Organic reactions 172:10.1021/cr400265z 38:benzoic anhydride 22:organic synthesis 327: 294: 287: 281: 280: 248: 242: 241: 217: 211: 210: 195:Chemical Reviews 190: 184: 183: 160:Chemical Reviews 151: 42:benzoyl chloride 32:by acylation of 335: 334: 330: 329: 328: 326: 325: 324: 300: 299: 298: 297: 288: 284: 249: 245: 218: 214: 191: 187: 152: 148: 143: 126: 103: 78:Intramolecular 65: 12: 11: 5: 333: 323: 322: 317: 312: 310:Name reactions 296: 295: 282: 243: 212: 185: 166:(9): 4960–92. 145: 144: 142: 139: 138: 137: 132: 125: 122: 121: 120: 115: 110: 109:(flavopiridol) 102: 99: 91: 90: 83: 76: 64: 61: 9: 6: 4: 3: 2: 332: 321: 318: 316: 313: 311: 308: 307: 305: 292: 286: 278: 274: 270: 266: 263:(1): 96–100. 262: 258: 254: 247: 239: 235: 231: 227: 223: 216: 208: 204: 200: 196: 189: 181: 177: 173: 169: 165: 161: 157: 150: 146: 136: 133: 131: 128: 127: 119: 116: 114: 111: 108: 105: 104: 95: 88: 84: 81: 77: 74: 70: 69: 68: 57: 53: 52:is obtained. 51: 47: 43: 39: 35: 31: 27: 23: 19: 290: 285: 260: 256: 246: 229: 225: 215: 198: 194: 188: 163: 159: 149: 72: 66: 33: 17: 15: 232:: 102–109. 304:Categories 141:References 320:Coumarins 118:Flavoxate 113:Dimefline 107:Alvocidib 63:Mechanism 48:called a 30:coumarins 26:chromones 277:98794444 201:: 1–62. 180:24555663 124:See also 101:Examples 87:hydroxyl 46:chromone 24:to form 71:Phenol 50:flavone 275:  178:  273:S2CID 176:PMID 40:(or 16:The 265:doi 234:doi 203:doi 168:doi 164:114 28:or 306:: 271:. 261:39 259:. 255:. 230:34 228:. 224:. 199:36 197:. 174:. 162:. 158:. 279:. 267:: 240:. 236:: 209:. 205:: 182:. 170:: 73:O 34:O

Index

organic synthesis
chromones
coumarins
benzoic anhydride
benzoyl chloride
chromone
flavone

aldol condensation
hydroxyl

Alvocidib
Dimefline
Flavoxate
Allan–Robinson reaction
Baker–Venkataraman rearrangement
"Chromone: A Valid Scaffold in Medicinal Chemistry"
doi
10.1021/cr400265z
PMID
24555663
doi
10.1021/cr60113a001
"Ueber eine Bildungsweise von Chromonderivaten"
doi
10.1002/cber.19010340119
"3-Benzoylquinoxalin-2(1H)-one in the Kostanecki-Robinson Reaction. Synthesis and Structure of 2-Oxo-4-phenylpyrano[2,3-b]quinoxaline"
doi
10.1023/A:1023028927007
S2CID

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