An Efficient Synthesis of Novel 3-[(Heteroaryl-2-ylimino)-methyl]-4-hydroxy-chromen-2-ones and Analogue of Tetrazole Derivatives and Their Antibacterial Activity

Abstract

Synthesis of a series of the substituted [(pyridinyl and pyrimidin-2-ylimino)-ethyl]-4-hydroxy-chromen-2-ones and their tetrazole derivates is presented in this study. By catalytic condensation of 4-hydroxy-3-acetylcoumarine 2 and 2-aminopyridines 3(a-d), 3-[(pyridin-2-ylimino)-ethyl]-4-hydroxy-chromen-2-ones 4(a-d) are synthesized in high yield. During the condensation reaction of 2 and 4-amino-2,6-dihydroxypyrimidine 3e, 3-[1-(2,6-Dihydroxy-pyrimidin-4-ylimino)-ethyl]-4-hydroxy-chromen-2-one 4e as condensation products is synthesized. In following series, by cyclization reactions of compounds 4 (a-e) with sodium azide, analogue 3-substituted pyridin-2-yl and pyrimidin-2-yl-5-methyl-2,5-dihydro-1H-tetrazol-5-yl]-4-hydroxy-chromen-2-one 5(a-e) are synthesized the products. Structural characterization of the synthesized products is done on the basis of spectrometric data. Antibacterial activity of the compounds 4(a-e) and 5(a-e) against S. aureus, E. coli and Klebsiella was examined by measuring the inhibition zones around the disks marked with the corresponding products solution. The impact of substitutions in antimicrobial is also explored. Compounds with polar groups have shown significant antibacterial activity against these microorganisms.

Keywords

• 4-hydroxy-chromen-2-one
• condensation
• cyclization
• antibacterial
• zones of inhibition