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Synthesis of new 2,2′-disubstituted 5,5′-dimethyl-4,4′-bitriazoles and 2-(4-Triazolyl)quinoxalines

✍ Scribed by Francesco Paolo Invidiata; Stefania Aiello; Giancarlo Furno'; Enrico Aiello; Daniele Simoni; Riccardo Rondanin

Publisher: Journal of Heterocyclic Chemistry
Year: 2000
Tongue: English
Weight: 382 KB
Volume: 37
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570370221

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✦ Synopsis

Abstract

Thermal rearrangement of 3‐acylisoxazole arylhydrazones allowed facile preparation of 2__H__‐1,2,3‐triazoles which were firstly reacted with isoamyl nitrite and then with an opportune arylhydrazine to produce the corresponding α‐hydroxyiminohydrazones 8a‐h. The reaction of compounds 8a‐h with phosphorus pentachloride afforded the desired 4,4′‐bitriazoles 1a‐h. The α‐hydroxyiminoketone derivative 7 or the α‐diketone 14 reacted easily with 1,2‐phenylenediamine to afford 1,2,3‐triazoles 2a‐c bearing the quinoxaline moiety at position 4. Improved yields of the quinoxalines 2a‐c were obtained when 1,2‐phenylenediamine was reacted with the dioxime 15.

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