NITRONES AND OXAZIRIDINES .45. FORMATION OF PYRROLO[1,2-A]INDOLES BY INTRAMOLECULAR NITRONE CYCLOADDITION

被引：11

作者：

BLACK, DS

CRAIG, DC

DEBDAS, RB

KUMAR, N

机构：

[1] School of Chemistry, University of New South Wales, Kensington, 2033, P.O. Box 1, N.S.W

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1993年 / 46卷 / 05期

关键词：

D O I：

10.1071/CH9930603

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The N-allylindole-2-carbaldehydes (5)-(8) and related methyl ketones (9)-(12) undergo reaction with N-methylhydroxylamine to give the cycloadducts (14)-(17) and (19)-(22), respectively. These adducts contain isoxazolidine rings fused to pyrrolo[1,2-a]indole systems. Corresponding cycloaddition of the N-propargylindole derivatives (24) and (25) could not be effected and the nitrone (26) was isolated. The adducts (14)-(17) underwent hydrogenolysis of the isoxazolidine N-O bond to give the amino alcohols (27)-(30), together with traces of the alcohols (31)-(34). X-Ray crystallographic data for the cycloadducts (15) and (16b) are presented.

引用

页码：603 / 622

页数：20

共 21 条

[1] COPE REARRANGEMENT AND INTERNAL CYCLOADDITION OF "5-ALLYL-3,3,5-TRIMETHYL-1-PYRROLINE 1-OXIDE [J].