3H-AZEPINES AND RELATED SYSTEMS .4. PREPARATION OF 3H-AZEPIN-2-ONES AND 6H-AZEPINO[2,1-B]QUINAZOLIN-12-ONES BY PHOTOINDUCED RING EXPANSIONS OF ARYL AZIDES

被引：38

作者：

LAMARA, K ^{[1
]}

SMALLEY, RK ^{[1
]}

机构：

[1] UNIV SALFORD,DEPT CHEM & APPL CHEM,SALFORD M5 4WT,LANCS,ENGLAND

来源：

TETRAHEDRON | 1991年 / 47卷 / 12-13期

关键词：

D O I：

10.1016/S0040-4020(01)96138-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photolysis of a series of p-substituted phenyl azides (p-X-C6H4N3; X = CO2Me, CO2Et, CN, CF3, SO2NH2, CO2CHPh2, COMe, CHO, and NO2) in 1:1 (nu/nu) 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-carboxylic acids, the former in admixture with decarboxylated material, and 6H-azepino[2,1-b]quinazolin-12-ones, are obtained by irradiation of 2-azidobenzoic acid and of 5-azidoisophthalic acid, respectively. The mode of formation of the azepino-quinazolinones is discussed.

引用

页码：2277 / 2290

页数：14