Nonconcerted Cycloaddition of 2H-Azirines to Acylketenes: A Route to N-Bridgehead Heterocycles

被引：15

作者：

Khlebnikov, Alexander F. ^{[1
]}

Novikov, Mikhail S. ^{[1
]}

Pakalnis, Viktoriia V. ^{[1
]}

Yufit, Dmitry S. ^{[2
]}

机构：

[1] St Petersburg State Univ, Dept Chem, St Petersburg 198504, Russia

[2] Univ Durham, Dept Chem, Durham DH1 3LE, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 22期

基金：

俄罗斯基础研究基金会;

关键词：

AZOMETHINE YLIDE; DIELS-ALDER; GENERATION; CARBENOIDS; BASE;

D O I：

10.1021/jo201563b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions of acylketenes, generated from diazo diketones, with 2-unsubstituted and 2-monosubstituted 3-aryl-2H-azirines lead to 1:1 or 2:1 adducts, which are derivatives of 5-oxa-1-azabicyclo[4.1.0]hept-3-ene or 5,7-dioxa-1-azabicyclo[4.4.1]undeca-3,8-diene. According to DFT B3LYP/6-31G(d) computations, the formation of (4+2)-monoadducts proceeds via a stepwise non-pericyclic mechanism. Reaction with methanol transforms quantitatively both 1:1 and 2:1 adducts into 1,4-oxazepine derivatives.

引用

页码：9344 / 9352

页数：9

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