☆ 4.6 Article

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

MOLECULES (2008)

Journal

MOLECULES

Volume 13, Issue 5, Pages 1066-1078

Publisher

MOLECULAR DIVERSITY PRESERVATION INT

DOI: 10.3390/molecules13051066

Keywords

dihydrothiophene; indolizine; aniline derivatives; biological activity

Categories

Biochemistry & Molecular Biology Chemistry, Multidisciplinary

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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 H-1- and C-13-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.

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