6533b82efe1ef96bd1293c3e

RESEARCH PRODUCT

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

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description

Thermal rearrangement of 3-acylisoxazole arylhydrazones allowed facile preparation of 2H-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.