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

Authors
BLACK DS CRAIG DC DEBDAS RB KUMAR N
Citation
Ds. Black et al., NITRONES AND OXAZIRIDINES .45. FORMATION OF PYRROLO[1,2-A]INDOLES BY INTRAMOLECULAR NITRONE CYCLOADDITION, Australian Journal of Chemistry, 46(5), 1993, pp. 603-622
Citations number
21
Categorie Soggetti
Chemistry
Journal title
Australian Journal of Chemistry → ACNP
ISSN journal
00049425
Volume
46
Issue
5
Year of publication
1993
Pages
603 - 622
Database
ISI
SICI code
0004-9425(1993)46:5<603:NAO.FO>2.0.ZU;2-V
Abstract
The N-allylindole-2-carbaldehydes (5)-(8) and related methyl ketones ( 9)-(12) undergo reaction with N-methylhydroxylamine to give the cycloa dducts (14)-(17) and (19)-(22), respectively. These adducts contain is oxazolidine rings fused to pyrrolo[1,2-a]indole systems. Corresponding cycloaddition of the N-propargylindole derivatives (24) and (25) coul d not be effected and the nitrone (26) was isolated. The adducts (14)- (17) underwent hydrogenolysis of the isoxazolidine N-O bond to give th e amino alcohols (27)-(30), together with traces of the alcohols (31)- (34). X-Ray crystallographic data for the cycloadducts (15) and (16b) are presented.