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Studies on the chemistry of pharmacologically active heterocycles. Part I. Acid hydrolysis of hydrazino‐1,2,4‐triazine derivatives
Author(s) -
Daneshtalab M.,
Khalaj A.,
Lalezari I.
Publication year - 1979
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.5570160444
Subject(s) - chemistry , nucleophile , triazine , hydrolysis , acid hydrolysis , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis
The acid hydrolysis of 3‐hydrazino‐5,6‐disubstituted‐1,2,4‐triazine, 3,5‐dihydrazino‐6‐substituted‐1,2,4‐triazine, and 2‐hydrazinopyrimidine derivatives was studied. It was found that the reaction proceeded through the formation of 3‐keto and 3,5‐diketo derivatives of the related 2,3‐dihydro, 2,3,4,5‐tetrahydro‐1,2,4‐triazines, and 2‐keto derivatives of 1,2‐dihydropyrimidines. It was concluded from these reactions that in 1,2,4‐triazine derivatives the C‐5 carbon is more reactive than the C‐3 carbon toward nucleophiles. The reaction mechanism is discussed.