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Synthesis of Triazolo[1,5-a]triazin-7-one Derivatives and Highly Functionalized [1,2,4]Triazoles

✍ Scribed by Montserrat Heras; David Font; Anthony Linden; José M. Villalgordo

Publisher: John Wiley and Sons
Year: 2003
Tongue: German
Weight: 161 KB
Volume: 86
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200390261

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✦ Synopsis

Abstract

The synthesis of novel triazolo[1,5‐a]triazin‐7‐ones is presented. Starting from 3‐amino‐5‐sulfanyl‐1,2,4‐triazole, the synthetic sequence involved alkylation with benzyl bromide, reaction with p‐nitrophenyl chloroformate followed by treatment with a primary amine, and condensation with diethoxymethyl acetate. Final oxidation of the thioether moiety with 3‐chloroperbenzoic acid provided 2‐(benzylsulfonyl)[1,2,4]triazolo[1,5‐a][1,3,5]triazin‐7‐ones 5a and 5b in good overall yields. Treatment of 5a and 5b with secondary amines provided highly functionalized [1,2,4]triazoles through an unexpected triazinone ring opening. A mechanism for this transformation is proposed.

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