Tetrahedron Letters p. 1673 - 1676 (1997)
Update date:2022-08-02
Topics:
Macor, John E.
Forman, James T.
Post, Ronald J.
Ryan, Kevin
A practical synthesis of pyrrolo[3,2-e]indole (1) is described. Different hydrogenation conditions of the indol-4-ylacetonitrile (3) afforded either 1-BOM-pyrrolo[3,2-e]indole (4, 42% from 5-nitroindole) or 1-hydroxymethylpyrrolo[3,2-e]indole (5, 46% from 5-nitroindole). Removal of the benzyl group was found to be problematic, but could be accomplished in moderate yield. Treatment of the resulting 1-hydroxymethylpyrrolo[3,2-e]indole (5) with NaOH in THF afforded 1 (94% from 5). Limited studies on the chemistry of 1 are also presented.
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