Tetrahedron

3H-Azepines and related systems. Part 4. Preparation of 3H-azepin-2-ones and 6H-azepino [2, 1-b] quinazolin-12-ones by photo-induced ring expansions of aryl …

K Lamara, RK Smalley

Index: Lamara, Kaddour; Smalley, Robert K. Tetrahedron, 1991 , vol. 47, # 12-13 p. 2277 - 2290

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Citation Number: 34

Abstract

Photolysis of a series of p-substituted phenyl azides (pX-C6H4N3; X= CO2Me, CO2Et, CN, CF3, SO2NH2, CO2CHPh2, COMe, CHO, and NO2) in 1: 1 (v/v) THF-water solution produces, in the majority of cases, a 5-substituted-3H-azepine-2-one. In a like manner, 3H- azepin-2-one-3-carboxylates can be prepared from 5-substituted-2-azidobenzoates, providing the 5-substituent is electron-withdrawing. 3H-Azepin-2-one mono-and di- ...