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

Molecules 2008, 13, 1066-1078; DOI: 10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /molecules Article Facile Synthesis of Heterocycles via 2-Picolinium Bromide and Antimicrobial Activities of the Products Elham S. Darwish Department of Chemistry, Faculty of Science, University of Cairo, Giza, 12613, Egypt; E-mail: elham_darwish@ Received: 3 April 2008; in revised form: 24 April 2008 / Accepted: 24 April 2008 / Published: 1 May 2008 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. Keywords: Dihydrothiophene, indolizine, aniline derivatives, biological activity Introduction Many thiophene derivatives have been reported to exhibit interesting pharmaceutical properties, including antimicrobial [1], anticancer [2], anti-inflammatory [3], bacteriostatic and fungistatic activity [4]. Some other derivatives exhibit strong inhibition of NHE-1 and cardioprotective efficacy [5]. Indolizine derivatives also possess valuable biological