A new regiospecific method for the synthesis of substituted phenanthridines and benzo[j]phenanthridines via aromatic annelation of 1-N-benzenesulfonyl-3-[bis(methylthio)methylene]-1,2,3,4-tetrahydroquinoline-4-one

被引：32

作者：

Patra, PK ^{[1
]}

Suresh, JR ^{[1
]}

Ila, H ^{[1
]}

Junjappa, H ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

TETRAHEDRON | 1998年 / 54卷 / 34期

关键词：

D O I：

10.1016/S0040-4020(98)00609-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new efficient method for the synthesis of substituted phenanthridines, benzo[j]phenanthridines and naphtho[2,1-j]phenanthridines is described. The method involves reaction of alpha-oxoketene dithioacetal 2 with allyl (3a), methallyl (3b), benzyl (11a-f) and 1-naphthylmethyl (20) magnesium halides followed by cyclization of the resulting carbinolacetals in the presence of BF3.Et2O in refluxing benzene. The dihydrophenanthridines thus obtained were aromatized by treatment with a base in the presence of phase transfer catalyst. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：10167 / 10178

页数：12

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