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Molecules 2008, 13(5), 1066-1078; doi:10.3390/molecules13051066

Facile Synthesis of Heterocycles via 2-Picolinium Bromide and Antimicrobial Activities of the Products

Department of Chemistry, Faculty of Science, University of Cairo, Giza, 12613, Egypt
Received: 3 April 2008 / Revised: 24 April 2008 / Accepted: 24 April 2008 / Published: 1 May 2008
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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 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 Dihydrothiophene; indolizine; aniline derivatives; biological activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Darwish, E.S. Facile Synthesis of Heterocycles via 2-Picolinium Bromide and Antimicrobial Activities of the Products. Molecules 2008, 13, 1066-1078.

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