Turkish Journal of Chemistry, Vol.36, No.1, 81-91, 2012
Four-component synthesis of 1,3,4-oxiadiazole derivatives from N-isocyaniminotriphenylphosphorane, aromatic carboxylic acids, aromatic bis-aldehydes, and secondary
The 1:1 iminium intermediate generated by the addition of a secondary amine to aromatic bis-aldehydes (isophthalaldehyde and terphthalaldehyde) is trapped by the N-isocyaniminotriphenylphosphorane in the presence of a aromatic carboxylic acid derivative, which leads to the formation of corresponding iminophosphorane intermediate. Then disubstituted 1,3,4-oxadiazole derivatives are formed via intramolecular aza-Wittig reaction of the iminophosphorane intermediates. The reactions were completed in neutral conditions at room temperature and the corresponding disubstituted 1,3,4-oxadiazole derivatives were produced in excellent yields.
Keywords:N-isocyaniminotriphenylphosphorane;aromatic carboxylic acid;aromatic bis-aldehydes;1,3,4-oxadiazole;aza-Wittig reaction;secondary amine