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

Molecules

关键词: Dihydrothiophene;    indolizine;    aniline derivatives;    biological activity;   

DOI  :  10.3390/molecules13051066

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2008 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland.