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Synthesis of substituted dihydrobenzo[ f ]pyrimido[4,5‐ b ]‐quinolines as tetracyclic 5‐deaza nonclassical folates
Author(s) -
Donkor Isaac O.,
Gangjee Aleem,
Duah Francis K.
Publication year - 1990
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.5570270353
Subject(s) - chemistry , quinoline , structural isomer , aldehyde , stereochemistry , organic chemistry , catalysis
Abstract Cyclocondensation of 2,4,6‐triaminopyrimidine ( 10 ) with chlorovinyl aldehyde 7 afforded the linear regioisomer 9,1 1‐diamino‐5,6‐dihydrobenzo[ f ]pyrimido[4,5‐ c ]quinoline ( 1 ) while the cyclocondensation of 2,6‐diamino‐4‐hydroxypyrimidine ( 11 ) or 6‐amino‐2,4‐dihydroxypyrimidine ( 12 ) with chlorovinyl aldehyde 7 was regiospecific affording the linear regioisomers 9‐amino‐11‐oxo‐5,6‐dihydrobenzo[ f ]pyrimido[4,5‐ c ]quinoline ( 2 ) and 9,11‐dioxo‐5,6‐dihydrobenzo[ f ]pyrimido[4,5‐ c ]quinoline ( 3 ) respectively. The linear structures of these compounds were established by 1 H nmr and 13 C nmr spectral data.