Synthesis of novel indolizine, pyrrolo[1,2-a] quinoline, and 4,5-dihydrothiophene derivatives via nitrogen ylides and their antimicrobial evaluation

Abstract

Treatment of 2-(2-bromoacetyl)-3H-benzo[f ]chromen-3-one with pyridine, quinoline, and 2-methylquinoline afforded the corresponding pyridinium, quinolinium and 2-methylquinolinium bromides. The latter salts underwent [3 + 2] 1,3-dipolar cycloaddition with some electron deficient acetylene and ethylene derivatives to give the corresponding indolizine and pyrrolo[1,2-a]quinoline derivatives. Moreover, 2-(2-bromoacetyl)-3H-benzo[f ]chromen-3-one reacted with arylidene cyanothioacetamides to afford the corresponding 2-amino-4,5-dihydrothiophene-3-carbonitriles. The synthesised compounds were characterised based on their elemental analysis and spectral data. Antimicrobial activity of some of the synthesised compounds was evaluated.