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A simple one pot synthesis of condensed 1,2,4-triazines by using the tandem aN-SNipso and SNH-SNipsa reactions

✍ Scribed by Oleg N. Chupakhin; Gennady L. Rusinov; Dmitry G. Beresnev; Valery N. Charushin; Hans Neunhoeffer

Publisher: Journal of Heterocyclic Chemistry
Year: 2001
Tongue: English
Weight: 84 KB
Volume: 38
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570380414

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✦ Synopsis

A new synthetic approach to condensed 1,2,4-triazines based on using the tandem A N -S N ipso and S N H -S N ipso reactions has been developed. 5-Methoxy-3-penyl-1,2,4-triazine and its N 1 -methyl quaternary salt were found to react with C,N-, C,O-and N,N'-bifunctional nucleophiles (m-phenylenediamine, resorcinol, semicarbazide and ureas) into triazacarbazoles, benzofuro[2,3-e][1,2,4]-triazines, and 6-azapurine derivatives. In all cases nucleophiles attack first the unsubstituted C-6 carbon of the triazine ring, while the final stage is replacement of the methoxy group affording cyclization products.

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