Trapping of photochemical intermediates as a tool in organic synthesis. Preparation of spiroaziridinopyridones, a new heterocyclic system

被引：10

作者：

Donati, D ^{[1
]}

Fusi, S ^{[1
]}

Ponticelli, F ^{[1
]}

机构：

[1] Univ Siena, Dept Chem, I-53100 Siena, Italy

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 52期

关键词：

condensed pyridines; photochemical intermediates trapping; ketenimines; aziridines;

D O I：

10.1016/S0040-4039(02)02438-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Whereas alkyl lithium and Grignard reagents both at rt and at -80degreesC thermally react with 3-methylisoxazolo[5,4-b]pyridine giving alkylation and/or isoxazole ring opening products, sodium malonate and sodium boron hydride react only under UV irradiation. Selective trappings of ketenimine or azirine intermediates give an enaminopyridone or two diasteroisomeric spiroaziridinopirydones. Regioselective opening of the aziridine ring with perchloric acid gives 3(1-amino-ethyl)-1H-pyridin-2-one. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：9527 / 9530

页数：4

共 7 条

[1] Aminocyclopentitols from N-alkylpyridinium salts:: A photochemical approach [J].