ISSN: 1813-0410

Author : M.Radhi, Sajid


Synthesis of Some New 1, 3, 4-Oxadiazole Derivatives Containing Azo Group from 5-[4-(p- Methoxyphenyl)azophenyl]- 2-thiol- 1, 3, 4 – oxadiozole

Zaid H.Abood; Rahman T. Haiwal; Sawsan K.Abbas; Sajid M.Radhi; Rabab K.Hameem

journal of kerbala university, 2008, Volume 4, Issue 1, Pages 147-160

In this paper , the synthesis of 1,3,4-Oxadiazole derivatives containing azo group were achieved from 5-[4- ( P-methoxyphenyl ) azo phenyl ]-2- thiol-1,3,4-Oxadiazole [4].Treatment of compound [4] with ethyl 1- chloroacetate in alcoholic potassium hydroxide resulted in the formation of 2-thioester derivative [5] which was then converted to acid hydaizide derivative [6] by the reaction with hydrazine hydrate in ethanol .The reaction of hydrazide with carbon disulfide in alcoholic potassium hydroxide afforded 2 - [5 - (4 -(P - methoxyphenyl ) azophenyl ) -1,3,4 – oxadizol- 2 -yl methylthio ] - 1,3,4 - oxadiazole -5- thiol [7] . the latter was treated with propargyl bromide in basic media to give (5- propynyl)thio derivative [ 8 ] which was then treated with formaldehyde and piperidine to give5-(4-piperidino)butynylthio derivative[9]. Compound [7] was also treated with n-butyl chloride in basic media to give 5 - thioalkyl derivative [ 10 ] which was then oxidized with potassium permanganate in acidic media to give 5-sulfonylalkyl derivative [11]. The structures of the sythesised compounds were confirmed by melting points ,FT-IR spectra as well as elemental microanalysis.