Synthesis of Various Fused Heterocyclic Rings from Oxoindenyl Esters and their Pharmacological and Antimicrobial Evaluations

Abstract

Methyl (Z)-2-O-carboxyphenyl-3-(3,4,5-trimethoxyphenyl)acrylate 1 was prepared and cyclized in different conditions to give the indenone 2. Also, 1 was utilized to synthesize the isochroman dione derivatives 8, 10, 12, and 13 and isoquinoline derivatives 16 and 18. On the other hand, the reactions of 2 with some nucleophilic reagents such as Grignard reagents and hydrazine derivatives afforded the novel heterocyclic systems 3, 4a,b, 5, 6, and 7. Isochroman dione 12 was allowed to react with primary amines to give 14, 15, 17, and 19. The structures of the synthesized new compounds have been elucidated by spectroscopic data: IR, 1H-NMR, 13C-NMR, mass spectra, and elemental analyses. The antimicrobial and anticancer activities have been evaluated.