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Paper | Regular issue | Vol 38, No. 5, 1994, pp.981-989
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6565
Ring Transformation of Heterocycles: Part 3. A Conversion of 4-Amino-Δ2-1,2,4-oxadiazolines into 2-Arylamino-1,3,4-thiadiazoles and Oxaanalogues

Ahmad Q. Hussein,* Mustafa M. El-Abadelah, Musa Z. Nazer, and Abdel M. Awadallah

*Chemistry Department, Faculty of Science, University of Jordan, Amman 11942, Jordan


4-Amino-Δ2-1,2,4-oxadiazolines (1) are transformed into the corresponding 2-arylamino-1,3,4-oxadiazoles (5) or thiadiazoles (6) via reaction with phenyl isocyanate ( or phenyl isothiocyanate), followed by brief treatment of the resulting adducts (2 and 3) with trifluoroacetic anhydride at ambient temperature. Treatment of compounds (1) with trifluoroacetic anhydride gave 2-trifluoromethyl-1,3,4-oxadiazoles (8).