Facile synthesis of heterocycles via 2-picolinium bromide and antimicrobial activities of the products.
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 MnO(2) yielded the products 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 by elemental analysis as well as by (1)H- and (13)C-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.
Darwish
Elham S
ES
Department of Chemistry, Faculty of Science, University of Cairo, Giza, 12613, Egypt. elham_darwish@yahoo.com
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D005658:Fungi / Q000187:drug effects; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D010847:Picolines / Q000737:chemistry*; D013057:Spectrum Analysis
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D006571:Heterocyclic Compounds; D010847:Picolines; C530793:2-picoline