SYNTHESIS AND REACTIVITY OF PYRROLO[3,2-E]INDOLE - REMOVAL OF A N-BOMGROUP FROM AN UNACTIVATED INDOLE

Authors
MACOR JE FORMAN JT POST RJ RYAN K
Citation
Je. Macor et al., SYNTHESIS AND REACTIVITY OF PYRROLO[3,2-E]INDOLE - REMOVAL OF A N-BOMGROUP FROM AN UNACTIVATED INDOLE, Tetrahedron letters, 38(10), 1997, pp. 1673-1676
Citations number
8
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
10
Year of publication
1997
Pages
1673 - 1676
Database
ISI
SICI code
0040-4039(1997)38:10<1673:SAROP->2.0.ZU;2-0
Abstract
A practical synthesis of pyrrolo[3,2-e]indole (1) is described. Differ ent hydrogenation conditions of the indol-4-ylacetonitrile (3) afforde d either 1-BOM-pyrrolo[3,2-e]indole (4, 42% from 5-nitroindole) or 1-h ydroxymethylpyrrolo[3,2-e]indole (5, 46% from 5-nitroindole). Removal of the benzyl group was found to be problematic, but could be accompli shed in moderate yield. Treatment bf the resulting 1-hydroxymethylpyrr olo[3,2-e]indole (5) with NaOH in THF afforded 1 (94% from 5). Limited studies on the chemistry of 1 are also presented. (C) 1997 Elsevier S cience Ltd.