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The synthesis of pyridoquinolines with dialkylaminopropylamine side chains
Author(s) -
Molock Frank F.,
Boykin David W.
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.5570200335
Subject(s) - chemistry , side chain , phenanthroline , saponification , quinoline , michael reaction , dimethyl acetylenedicarboxylate , medicinal chemistry , organic chemistry , polymer chemistry , catalysis , polymer , cycloaddition
Several new pyridoquinolines with dimethylaminopropyl side chain including 4,7‐bis(3′‐dimethylaminopropylamino)‐1,10‐phenanthroline ( 1 ), 4,10‐bis(3′‐dimethylaminopropylamino)‐1,7‐phenanthroline ( 2 ), 4,10‐bis(3′‐dimethylaminopropylamino)‐6‐methyl‐1,7‐phenanthroline ( 3 ), 4,6‐bis(3′‐dimethylaminopropylamino)‐10‐methylpyrido[3,2‐g]quinoline ( 4 ) and 4‐(3′‐dimethylaminopropyl)pyrrolo[lmn][4,7]phenanthroline (5) have been prepared. The compounds were prepared by a multi‐step synthesis which begins with Michael type addition of dimethyl acetylenedicarboxylate or diethyl ethoxymethylenemalonate to the appropriate phenylenediamine. The enamines obtained from the Michael addition were cyclized on heating at elevated temperatures to form the corresponding pyridoquinoline‐diester‐diones. The diester‐diones were saponified decarboxylated and converted into dichloropyridoquinolines which on reaction with dimethylaminopropylamine yielded the title compounds.