2-SUBSTITUTED-3-ACYLINDOLES THROUGH THE PALLADIUM-CATALYZED CARBONYLATIVE CYCLIZATION OF 2-ALKYNYLTRIFLUOROACETANILIDES WITH ARYL HALIDES AND VINYL TRIFLATES

被引：123
作者：
ARCADI, A
CACCHI, S
CARNICELLI, V
MARINELLI, F
机构：
[1] UNIV ROMA LA SAPIENZA,DIPARTIMENTO STUDI CHIM & TECNOL SOSTANZE BIOL AT,I-00185 ROME,ITALY
[2] UNIV URBINO,FAC SCI,IST CHIM ORGAN,I-61020 URBINO,ITALY
[3] UNIV LAQUILA,DIPARTIMENTO CHIM INGN CHIM & MAT,I-67100 LAQUILA,ITALY
来源：
TETRAHEDRON | 1994年 / 50卷 / 02期
关键词：
D O I：
10.1016/S0040-4020(01)80766-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The palladium-catalysed reaction of readily accessible 2-alkynyltrifluoroacetanilides with aryl halides and vinyl triflates under a carbon monoxide atmosphere (1 or 7 atm) and in the presence of potassium carbonate produces 2-substituted-3-acyl indoles in fair to good yield. The acidity of the nitrogen-hydrogen bond proved to be of primary importance for the success of the reaction. The methodology has been applied to the synthesis of pravadoline, a drug that shows analgesic activity against postoperative pain in man.
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页码：437 / 452
页数：16
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