Condensation of 4-phenyl-3,5-dicarboethoxycyclopentane-1,2-dione with primary amines

Condensation of the title compound ( 1 ) with primary aromatic amines gave the dianilides ( 2 ), which cyclized to cyclopenta1,2-c:4,3-c′]diquinolines ( 3 ). Treatment of 1 with o-phenylenediamine or 2,3-diaminopyridine afforded cyclopenta2,1-b:3,4- b ′]bis1,5]benzodiazepine ( 4 ) and bis1,5]pyridob]diazepine derivative ( 5 ), respectively. Whereas, with o-aminophenol a mixture of 2c and cyclopenta2,1- b :3,4- b ′]bis1,5]benzoxazepine ( 7 ) was obtained. Pechmann reaction of 1 with m-cresol gave the bis1]benzopyrane ( 9 ). Mannich reaction of 1 with benzylamine afforded the 3-azabicyclo3.2.1]octane system ( 10 ).