Facile synthesis of heterocycles via 2-picolinium bromide and antimicrobial activities of the products

Abstract

The 2-picolinium N-ylide 4, generated in situ from the N-acylmethyl-2- picolinium bromide 3, underwent cycloaddition to N-phenylmaleimide or carbon disulfide to give the corresponding cycloadducts 6 and 8, respectively similar reactions of compound 3 with some electron-deficient alkenes in the presence of MnO2 yielded the products 11 and 12. In addition, reaction of 4 with arylidene cyanothioacetamide and malononitrile derivatives afforded the thiophene and aniline derivatives 15 and 17, respectively. Heating of picolinium bromide 3 with triethylamine in benzene furnished 2-(2-thienyl)indolizine (18). The structures of the isolated products were confirmed by elemental analysis as well as by 1H- and 13C-NMR, IR, and MS data. Both the stereochemistry and the regioselectivity of the studied reactions are discussed. The biological activity of the newly synthesized compounds was examined and showed promising results. © 2008 by the author(s); licensee Molecular Diversity Preservation International.