Synthesis and Antimicrobial Activity of Some Novel bis Polyfunctional Pyridine, Pyran, and Thiazole Derivatives

In continuation of our efforts to find a new class of antimicrobial agents, treatment of N,N′-(1,4-phenylene)bis(2-cyanoacetamide) (1) with formaldehyde and either benzoylacetonitrile or malononitrile to afford pyridine derivatives 5 and 8, respectively. Similarly, treatment of 1 with different types of aldehydes afforded benzylidene derivatives 9–15, followed by the reaction with rmalononitrile dime to give polyfunctional pyridine derivative 18. Moreover, cyanoacetamide 1 was reacted with chalcone, benzylidenemalononitrile, and 1,3-diketone to afford pyran derivatives 21, 25, and 28, respectively, followed by the reaction with ammonium acetate to afford polyfunctional pyridine derivatives 22, 26, and 29, respectively. Furthermore, thiazole derivative 32 was prepared via treatment of 1 with elemental sulfur and phenyl isothiocyanate. The newly synthesized compounds were evaluated as antimicrobial activities.