Diels-Alder cycloaddition of 2-azadienes to methyl 2-(2,6-dichlorophenyl)-2H-azirine-3-carboxylate in the synthesis of methyl 4-oxo-1,3 diazabicyclo[4.1.0]heptane-6-carboxylates

被引：16

作者：

Alves, MJ ^{[1
]}

Duraes, MM ^{[1
]}

Fortes, AG ^{[1
]}

机构：

[1] Univ Minho, Dept Quim, P-4700320 Braga, Portugal

来源：

TETRAHEDRON | 2004年 / 60卷 / 31期

关键词：

2-azadienes; 2H-azirines; Diels-Alder cycloaddition;

D O I：

10.1016/j.tet.2004.06.004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A number of fused 4-oxo-1,3-diazabicyclo[4.1.0]heptane-6-carboxylates, a new type of compound, have been obtained by Diels-Alder cycloaddition between nucleophilic 2-azadienes and an electrophilic 2H-azirine. The reactions are completely endo- and regioselective, the azirine being added by its less hindered face to the diene. There are two isomers 7 and 8 formed from dienes 1 due either to isomerization of the cycloadducts 7 and 8 or by isomerization of the C=N bond of the diene during the reaction. The isomer 10 is formed from diene 2e, and a single diastereoisomer structure 4a-i is formed from dienes 11. Some pyrimidones 8a, 7c/8c, 7e, 10, 11d have been hydrolyzed leading to functionalised aziridines 12, 13 and 15. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：6541 / 6553

页数：13

共 19 条

[1] Diastereoselective synthesis of aziridines from (1R)-10-(N,N-dialkylsulfamoyl)isobornyl 2H-azirine-3-carboxylates [J].