Cyclization of N-benzyl cyanoacetamide: Novel synthesis and biological activity of pyrrole,pyrimidine, and pyran derivatives

Heteroannulation of N-Benzyl cyanoacetamide 1 to a new series of heterocycles has been developed. Thus, reaction of 1 with different polarized π systems afforded pyrrolo 4 , pyridone 6 , pyridine 8 , and diazapene 10 derivatives, respectively. N-Benzyl cyanoacetamide that undergo condensation reaction with salicylaldehyde yielded pyran derivative 11 . Nitrosation of 11 furnished condensed pyran 13 . Compound 11 reacted with benzaldehyde, carbon disulfide (cyclizing agent), and ammonium thiocyanate to provide pyrane 17 , thiazine 18 , and thiourea 20 derivatives, respectively. Cinnamoyl isothiocyanate was reacted with compound 11 to produce non-isolable thiourea derivative 21 . The newly synthesized compounds have been characterized by infrared (IR), proton nuclear magnetic resonance (¹H NMR), and carbon nuclear magnetic resonance (¹³C NMR) spectral data. The compounds were then evaluated for antibacterial and anticancer activities.