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 disulfideto give the corresponding cycloadducts 6 and 8, respectively similar reactions ofcompound 3 with some electron-deficient alkenes in the presence of MnO2 yielded theproducts 11 and 12. In addition, reaction of 4 with arylidene cyanothioacetamide andmalononitrile 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 byelemental analysis as well as by 1H- and 13C-NMR, IR, and MS data. Both thestereochemistry and the regioselectivity of the studied reactions are discussed. Thebiological activity of the newly synthesized compounds was examined and showedpromising results.

Keywords

• Dihydrothiophene
• indolizine
• aniline derivatives
• biological activity