Synthesis of highly-functionalised pyridines via hetero-Diels-Alder methodology: reaction of 3-siloxy-1-aza-1,3-butadienes with electron deficient acetylenes

被引：67

作者：

Fletcher, Matthew D.

Hurst, Timothy E.

Miles, Timothy J.

Moody, Christopher J.

机构：

[1] Univ Exeter, Dept Chem, Exeter EX4 4QD, Devon, England

[2] Univ Coll N Wales, Dept Chem, Bangor LL57 2UW, Gwynedd, Wales

[3] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

[4] GlaxoSmithKline, Harlow CM19 5AW, Essex, England

来源：

TETRAHEDRON | 2006年 / 62卷 / 23期

基金：

英国工程与自然科学研究理事会;

关键词：

hetero-Diels-Alder reaction; pyridines; microwave irradiation;

D O I：

10.1016/j.tet.2006.03.051

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The hetero-Diels-Alder reaction between 1-aza-3-siloxy-1,3-butadienes and electron deficient acetylenes is described. The reactivity of a range of alpha,beta-unsaturated oximes and hydrazones is assessed in the synthesis of tri- and tetra-substituted pyridines bearing an oxygen functionality at C-3. Microwave irradiation has been employed to decrease the extended reaction times and increase the poor yields often associated with this reaction. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：5454 / 5463

页数：10

共 39 条

[1] INTRAMOLECULAR AND INTERMOLECULAR DIELS-ALDER REACTIONS OF ACYLHYDRAZONES DERIVED FROM METHACROLEIN AND ETHYLACROLEIN [J].