Synthesis and alkylation of 1-alkyl(aryl)-4-cyano-3-dicyanomethylene-substituted carbo[c]fused pyridines. Molecular and crystal structure of 2-(4-cyano-1-methyl-5,6,7,8-tetrahydroisoquinolin-3-yl)-2-(2-oxo-2-phenylethyl)malononitrile and 10-amino-8-phenyl-5-(2-chlorophenyl)-1,2,3,4-tetrahydro-7H-pyrido[2′,3′:3,4]cyclopenta[1,2-c]isoquinoline-7,7,9-tricarbonitrile

Abstract

Condensation of 2-acyl-1-( N -morpholinyl)cycloalkene with malononitrile dimer results in 1-alkyl-(aryl)-4-cyano-3-dicyanomethylene-substituted carbo[ c ]fused pyridines. Reaction of the latter with alkyl halides affords the corresponding 2-alkyl-2-(3-isoquinolinyl)malononitrile, 1-amino-2-(4-bromobenzoyl)-5-(2-chlorophenyl)-6,7,8,9-tetrahydro-3 H -cyclopenta[ c ]isoquinoline-3,3-dicarbonitrile and 10-amino-8-phenyl-5-(2-chlorophenyl)-1,2,3,4-tetrahydro-7 H -pyrido[2′,3′:3,4]cyclopenta[1,2- c ]isoquinoline-7,7,9-tricarbonitrile. Structure of the latter and of 2-(1-methyl-4-cyano-5,6,7,8-tetrahydroisoquinolin-3-yl)-2-(2-oxo-2-phenylethyl)-malononitrile was investigated by XRD.