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A novel synthesis of indole derivatives by the reaction of N-arylhydroxamic acids with malononitrile

✍ Scribed by Yukihiko Tomioka; Kimiko Ohkubo; Hiroshi Maruoka

Publisher: Journal of Heterocyclic Chemistry
Year: 2007
Tongue: English
Weight: 386 KB
Volume: 44
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570440222

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✦ Synopsis

Abstract

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An approach to indole derivatives from N‐arylhydroxamic acids and malononitrile via a [3,3]‐sigmatropic rearrangement and intramolecular cyclization is described. Reactions of N‐arylhydroxamic acids 1a‐c, 2a‐c and 3a‐c with malononitrile in the presence of triethylamine at room temperature gave the corresponding α‐cyanoacetamide derivatives 4a‐c, 5a‐c, 6a‐c, 7a‐c and 8a‐c. Thermal treatment of 4a‐c, 5a‐c and 7a‐c with a base, e.g. triethylamine and sodium methoxide, caused intramolecular cyclization and deacylation to afford the corresponding indole derivatives 9‐11.

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