Synthesis of bioactive heterocyclic compounds using camphor

Abstract

The aim of the work was to synthesize novel heterocyclic compounds derived from camphor with antibacterial activity. The pyridazine, xanthene, pyranothiazole, pyridinothiazole, thiophene and pyrazole derivatives were produced from 4,11,11-trimethyl-9-phenyl-7-(2-phenylhydrazono)-3,4,5,6,7,9-hexahydro-1H-1,4-methanoxanthen-8(2H)-one (1). Thiophene derivatives 6a,b were produced according to the Gewald’s reaction for  thiophene synthesis. On the other hand, pyranothiazol derivatives 8a,b were synthesized by the multicomponent reactions between xanthene derivative 5, benzaldehyde and ethylcyanoacetate or malononitrile in ethanol/triethylamine. Whereas, pyridinothiazole derivative 9 was produced in ethanol/ammonium acetate by the multicomponent reaction between xanthene derivative 5, benzaldehyde and malononitrile. The antibacterial activity of the synthesized compounds was evaluated against E. coli bacteria. All synthesized compounds showed moderate activity against E. coli bacteria.   

KEY WORDS: Anti-microbial, Camphor, Heterocyclic, Pyrazol-3(2H)-one, Thiazol-4(5H)-one, Thieno[3,2-d]thiazole, Xanthenes

Bull. Chem. Soc. Ethiop. 2024, 38(4), 1069-1076.                                                         

DOI: https://dx.doi.org/10.4314/bcse.v38i4.20