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An application of the mannich reaction using hydroxylamine and some of its derivatives. 6‐Substituted‐2,4‐diamino‐5,6,7,8‐tetrahydropyrimido[4,5‐ d pyrimidines
Author(s) -
Delia Thomas J.,
Kirt Diane D.,
Sami Salah M.
Publication year - 1983
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.5570200131
Subject(s) - chemistry , hydroxylamine , mannich reaction , substituent , amine gas treating , ring (chemistry) , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis
Hydroxylamine and some of its O ‐substituted derivatives ( 2 ) have been used as the amine component in Mannich reactions with 2,4,6‐triaminopyrimidine ( 1 ). The resulting 6‐substituted tetrahydropyrimido[4,5‐ d ]‐pyrimidines ( 3 ) contain an N‐0 bond linking the substituent to the ring. These results extend the utility of this modified Mannich reaction to otherwise inaccessible substituents. Reaction conditions, spectral data and certain limitations of the reaction are discussed.