LITHIUM ALUMINUM HYDRIDE REDUCTION PRODUCTS FROM HETEROCYCLES CONTAINING AN ISOINDOLONE NUCLEUS

被引:20
作者
AEBERLI, P
HOULIHAN, WJ
机构
[1] Sandcz Pharmaceuticals, Hanover
关键词
D O I
10.1021/jo01258a042
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The lithium aluminum hydride reduction of a number of fused isoindolones (1) has been carried out in refluxing diethyl ether or tetrahydrofuran. Product composition was dependent on the type of heteroatom Y and the size of the fused ring A. All compounds where Y = O (5a-c, 8,11) gave isoindolines as the major product while those with Y = NR (13b and c, 26) gave isoindoles. When Y = NH the products were either medium-sized heterocycles (14 and 23) or isoindoles (15c and d, 19, 22a-c). A mechanism is proposed to account for the variation in product composition. © 1969, American Chemical Society. All rights reserved.
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页码:1720 / &
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