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.
N-isocyaniminotriphenylphosphorane, aromatic carboxylic acid, aromatic bis-aldehydes, 1, 3, 4-oxadiazole, aza-Wittig reaction, secondary amine
RAMAZANI, ALI; KARIMI, ZAHRA; SOULDOZI, ALI; and AHMADI, YAVAR
"Four-component synthesis of 1,3,4-oxadiazole derivatives from N-isocyaniminotriphenylphosphorane, aromatic carboxylic acids, aromatic bis-aldehydes, and secondary amines,"
Turkish Journal of Chemistry: Vol. 36:
1, Article 6.
Available at: https://journals.tubitak.gov.tr/chem/vol36/iss1/6