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

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

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Received: 3 April 2008; in revised form: 24 April 2008 / Accepted: 24 April 2008 / Published: 1 May 2008
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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
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MDPI and ACS Style

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

AMA Style

Darwish ES. Facile Synthesis of Heterocycles via 2-Picolinium Bromide and Antimicrobial Activities of the Products. Molecules. 2008; 13(5):1066-1078.

Chicago/Turabian Style

Darwish, Elham S. 2008. "Facile Synthesis of Heterocycles via 2-Picolinium Bromide and Antimicrobial Activities of the Products." Molecules 13, no. 5: 1066-1078.


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