Diels-Alder reactions of pyridine o-quinodimethane analogues generated from functionalised o-bis(chloromethyl)pyridines.

被引：32

作者：

Carly, PR ^{[1
]}

Cappelle, SL ^{[1
]}

Compernolle, F ^{[1
]}

Hoornaert, GJ ^{[1
]}

机构：

[1] KATHOLIEKE UNIV LEUVEN,DEPT CHEM,SYNTH ORGAN LAB,B-3001 HEVERLEE,BELGIUM

来源：

TETRAHEDRON | 1996年 / 52卷 / 36期

关键词：

D O I：

10.1016/0040-4020(96)00680-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The polyfunctional 2,3- and 3,4-o-bis(chloromethyl)pyridines 3, produced vip cycloaddition of the oxazinones 2 with propargyl chloride and 1,4-dichloro-2-butyne, were used as precursors of various pyridine o-quinodimethane analogues. The 2,3- and 3,4-dimethylenepyridine systems were generated via reductive 1,4-elimination with iodide and trapped in situ with various dienophiles to form the tetrahydroquinoline and -isoquinoline type adducts. A regiospecific cycloaddition was observed for the 3,4-dimethylenepyridine system with electron-rich dienophiles, i.e. dihydrofuran and ethyl vinyl ether, in contrast to the reaction with methyl acrylate. Copyright (C) 1996 Elsevier Science Ltd.

引用

页码：11889 / 11904

页数：16

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