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

被引：124

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.

引用

页码：437 / 452

页数：16

共 40 条

[21] PALLADIUM(0)-CATALYZED CARBOXYLATIVE CYCLIZED COUPLING OF PROPARGYLIC ALCOHOL WITH ARYL HALIDES [J].