Facile and selective synthesis of chloronicotinaldehydes by the Vilsmeier reaction

被引：59

作者：

Gangadasu, B. ^{[1
]}

Narender, P. ^{[1
]}

Bharath, S. ^{[1
]}

Ravinder, Kumar M. ^{[1
]}

Rao, B. Ananda ^{[1
]}

Ramesh, Ch. ^{[1
]}

Raju, B. China ^{[1
]}

Rao, V. Jayathirtha ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Chem Div 2, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON | 2006年 / 62卷 / 35期

关键词：

enamides; Vilsmeier reaction; diphosgene/triphosgene; chloronicotinaldehydes; selectivity; mechanism;

D O I：

10.1016/j.tet.2006.06.026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Eleven enamides were prepared by adopting different procedures. The various enamides prepared were subjected to Vilsmeier reaction using (i) POCl3/DMF; (ii) diphosgene/DMF; (iii) triphosgene/DMFleading to the formation of various multisubstituted chloronicotinaldehydes. Studies carried out indicate that Vilsmeier reagent concentration and the replacement of POCl3 by diphosgene or triphosgene, provides excellent selectivity and higher yields. Under modified reaction conditions one can get only chloronicotinaldehydes and not the chloropyridines as products. The various advantages in using diphosgene and triphosgene are illustrated. The mechanism of formation of chloronicotinaldehyde was discussed. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：8398 / 8403

页数：6

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