Synthesis of fluorine containing 1, 3, 4-oxadiazole derivatives as potential antifungal agents
Anil Kumar Mittal1, Dharm Veer Singh2, Satyaprakash Tripathi3*
Journal Title:Journal of Chemical, Biological and physical sciences
The synthesis of a number of 1, 3, 4-oxadiazole derivatives have been described 2, 4-Dichloro-sfluorobenzoyl
hydrazine (1) on reacting with aromatic acids in presence of phosphorus oxychloride
affords 5,2-Disubstituted-1, 3, 4-oxadiazoles or 2-Aroyl-5-(2,4-dichloro-5-fluorophenyl)-1,3,4-adiazoles
(2 a-i). Aroyl hydrazine on reacting with carbon disulphide under basic condition gives 5-(2, 4-Dichloro-
5-fluorophenyl)-1, 3, 4-oxadiazol-2-thione (3). Oxadiazol-2-thiones (3) are regioselectively
aminomethylated to give 3-(substituted methylamino)-5-(2, 4-dichloro-5-fluorphenyl)-1, 3, 4-
oxadiazol-2-thiones (4 a-i). Further, compounds (3) undergoes regioselective alkylation on treating
with alkyl / aroyl halides to give 2-Thioaryl-5-(2, 4-dichloro-5-fluorophenyl)-1, 3, 4-oxadiazoles (5 a-i).
Antifungal activity has been compared with Dithane M-45. A commercial fungicide, for their fungitoxic
action against Phytopthora infestance and Collectotricum falcatum, and the result correlated with
their structural features.