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Furan ring opening - indole ring closure: Synthesis of furo[2′,3′:3,4]-cyclohepta[1,2-b]indolium chlorides

✍ Scribed by Alexander V. Butin; Sergey K. Smirnov; Tatyana A. Stroganova

Publisher: Journal of Heterocyclic Chemistry
Year: 2006
Tongue: English
Weight: 365 KB
Volume: 43
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570430315

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✦ Synopsis

Abstract

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A new synthetic approach to furo[2′,3′:3,4]cyclohepta[1,2‐b]indolium chlorides is elaborated starting from 2‐acetylaminoaryldifurylmethanes or 2‐aminoaryldifurylmethanes under treatment with methanolic HCl solution. The reaction proceeds in three steps: recyclization, intramolecular cyclization, and disproportionation. In this case the furan ring takes part in building up both pyrrole and seven‐membered rings. The same salts can be obtained directly from 2‐acetylaminobenzaldehydes and 2‐methylfuran under similar conditions without isolation of corresponding 2‐acetylaminoaryldifurylmethanes.

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