Palladium-catalyzed heteroannulation with acetylenic carbinols as synthons - Synthesis of quinolines and 2,3-dihydro-4(1H)-quinolones

被引：72

作者：

Mahanty, JS ^{[1
]}

De, M ^{[1
]}

Das, P ^{[1
]}

Kundu, NG ^{[1
]}

机构：

[1] INDIAN ASSOC CULTIVAT SCI,DEPT ORGAN CHEM,CALCUTTA 700032,W BENGAL,INDIA

来源：

TETRAHEDRON | 1997年 / 53卷 / 39期

关键词：

D O I：

10.1016/S0040-4020(97)00852-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

omicron-Iodoanilides 4 reacted with terminal acetylenic carbinols 5 under palladium-catalyzed conditions to yield omicron-substituted anilides 6. Most of the anilides 6 could be cyclized with NaOEt/EtOH to 2-arylquinolines 2. omicron-Iodoanilines 7 reacted with carbinols 5 leading to 8 which on palladium(II) assisted cyclisation afforded substituted quinolines 2. An excellent synthesis of the alkaloid dubamine (2n) is reported. Also, the anilides 6 on acid-catalyzed rearrangement, deprotection and cyclisation led to the 2-aryl-2,3-dihydro-4(1H)-quinolones 16. (C) 1997 Elsevier Science Ltd.

引用

页码：13397 / 13418

页数：22

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