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Synthesis of a substituted tetrahydropyrimido[4,5‐ c ][2,7]naphthyridine as a tricyclic 5‐deaza nonclassical folate
Author(s) -
Gangjee Aleem,
Ohemeng Kwasi A.
Publication year - 1985
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.5570220450
Subject(s) - chemistry , tricyclic , aldehyde , condensation , organic chemistry , medicinal chemistry , stereochemistry , catalysis , physics , thermodynamics
Condensation of 2,6‐diamino‐4‐hydroxypyrimidine with 1‐benzoyl‐1,2,3,6‐tetrahydropyrimidine‐5‐carboxal‐dehyde (4) afforded a mixture of angular and linear tricyclic tetrahydropyrimidonaphthyridines. Separation of the mixture was affected by fractional precipitation. Condensation of 2,4,6‐triaminopyrimidine with 1‐benzoyl‐4‐chloro‐1,2,3,6‐tetrahydropyridine (5) was regiospecific and afforded only the substituted angular tetra‐hydropyrimido[4,5‐ c ][2,7]naphthyridine (2). The vinyl aldehyde 4 and the chlorovinyl aldehyde 5 were prepared by modifications of literature procedures.