The synthesis of azole derivatives from 3-[(4-methylphenyl)amino]- propanehydrazide and its N'-phenylcarbamoyl derivatives, and their antibacterial activity

Article abstract of DOI:10.1007/s00706-012-0799-0

5-[2-[(4-Methylphenyl)amino]ethyl]-1,3,4-oxadiazol- 2(3H)-thione, 5-[2-[(4-methylphenyl)amino]ethyl]- 1,3,4-oxadiazol-2(3H)-one, N-(2,5-dimethyl-1H-pyrrol-1-yl)- 3-[(4-methylphenyl)amino]propanamide, and a series of N-[(phenylcarbamoyl)amino]-3-[(4-methylphenyl)amino]- propanamides and 3-[(4-methylphenyl)(phenylcarbamoyl)- amino]-N-[(phenylcarbamoyl)amino] propanamides, and their thio analogues were synthesized from 3-[(4-methylphenyl)- amino]propanehydrazide. 1,3,4-Oxadiazole-2(3H)-thione was converted to 4-amino-2,4-dihydro-5-[2-[(4-methylphenyl)- amino]ethyl]-3H-1,2,4- triazole-3-thione, whereas cyclization of N'-phenylcarbamoyl derivatives provided thiazole, oxadiazoles, and thiadiazole, as well as triazole derivatives. Two of the synthesized compounds exhibited good antibacterial activity against Rhizobium radiobacter. Springer-Verlag 2012.