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Reactions of diazo derivatives of 5‐membered heterocycles with hydrazines
Author(s) -
Shealy Y. Fulmer,
O'Dell C. Allen
Publication year - 1973
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570100528
Subject(s) - chemistry , diazo , hydrazine (antidepressant) , yield (engineering) , semicarbazide , carboxamide , imidazole , organic chemistry , medicinal chemistry , materials science , chromatography , metallurgy
Interaction of hydrazine or dimethylhydrazine with 5‐diazoimidazole‐4‐carboxamide produced, presumably via tetrazenes, high yields of 5‐azidoimidazole‐4‐carboxamide. In contrast, when semicarbazide reacted with either the diazoimidazole or the analogous diazo‐1,2,3‐triazole, the yield of the azidoheterocycle was low, and the yield of biurea, and presumably the aminoheterocycle, was high. 3‐Azidopyrazole‐4‐carboxamide was obtained from a reaction of hydrazine with the diazopyrazole. Both azido and amino derivatives were formed from reactions of diazo‐imidazole esters with hydrazine or thiosemicarbazide.