Synthesis of 2-Cinnamoyl-l,3-indandione Derivatives and their Reactions with Hydrazine, Hydroxylamine Hydrochloride, Thiourea, Secondary Amines and Diethyl Oxalate

E l S a y e d A f s a h , F a t h y A b d e l K a d e r A m e r a n d H a s s a n E t m a n Chemistry Department, Faculty of Science, Mansoura University, Mansoura, A. R. Egypt Z. Naturforsch. 84b, 502-506 (1979); received October 25, 1978 2-Cinnamoyl-1,3-indandione Derivatives A series of 2-cinnamoyl-l,3-indandiones (2a-e) were obtained by condensing 1 with aldehydes. Treatment of 2 a with hydrazine or hydroxylamine hydrochloride gave 2-(5-phenyl-2-pyrazolinyl or -isoxazolinyl)-1,3-indandione (3 and 5) respectively, and when treated with thiourea gave 2-(6-phenyl-2-thioxo-4-pyrimidinyl)-l,3-indandione (6). The formation of 2-(/3-piperidino-, -morpholinoand -arylmercaptohydrocinnamoyl)1,3-indandiones (7a-b and 8a-b) from 2 a was investigated. Compound 7 b when treated with hydrazine gave 9. The 2-(a,/?-dimorpholinohydrocinnamoyl) derivative (11) was obtained by the action of morpholine on the dibromo derivative (10). The Michael condensation of 2 a with ethyl acetoacetate or acetyl acetone was investigated. Treatment of 1 with benzaldehyde in (3:1) molar ratio gave 14, which reacted with diethyl oxalate to give 15. Cyclization of 15 with polyphosphoric acid lead to the formation of 16.