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Reaction of 9‐substituted 1‐aminoadenine with hydrazine
Author(s) -
Asano Shoji,
Itano Keiji,
Kohda Kohfuku,
Yamagata Yuriko
Publication year - 1996
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.5570330419
Subject(s) - chemistry , hydrazine (antidepressant) , methanol , imidazole , solvent , medicinal chemistry , organic chemistry , reaction mechanism , catalysis , chromatography
Reaction of 9‐substituted (methyl or benzyl) 1‐aminoadenines 1 with hydrazine afforded 9‐substituted 6‐hydrazinopurines 2 and 1‐substituted 5‐ammo‐4‐(4‐amino‐1,2,4‐triazol‐3‐yl)imidazole ( 4 ). The product ratio of 2 to 4 rose with increasing amounts of methanol used as the solvent. When the same reaction was carried out using 1,9‐dimethyladenine instead of 1 , compounds 2 and 4 were also obtained with N 6 ,9‐dimethyladenine. A possible mechanism for formation of 2 and 4 is discussed.