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Quinoxalines X. a new and convenient synthesis of 1H-Pyrazolo [3,4-b] quinoxalines (Flavazoles)

✍ Scribed by Gerhard Sarodnick; Torsten Linker

Publisher: Journal of Heterocyclic Chemistry
Year: 2001
Tongue: English
Weight: 87 KB
Volume: 38
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570380404

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✦ Synopsis

Abstract

Dedicated to Professor Gerhard Kempter on the occasion of his 70^th^ birthday Quinoxaline‐2‐aldoximes and ‐ketoximes (6) react with hydrazine, alkylhydrazines or arylhydrazines under acidic conditions to afford l__H__‐pyrazolo[3,4‐b]quinoxalines (flavazoles) (1). Since the oximes (6) are easily available from phenylenediamine, the herein described methodology provides a convenient two step entry to various functionalized flavazoles. Furthermore, acylation and alkylation of the 1‐unsubstituted l__H__‐pyrazolo[3,4‐b]quinoxalines 7 proceeds smoothly and in good yield to afford 31 different flavazoles 11 and 12.

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