Four-component synthesis of 1,3,4-oxiadiazole derivatives from N-isocyaniminotriphenylphosphorane, aromatic carboxylic acids, aromatic bis-aldehydes, and secondary

作者：Ramazani Ali^*; Karimi Zahra; Souldozi Ali; Ahmadi Yavar

来源：Turkish Journal of Chemistry, 2012, 36(1): 81-91.

DOI：10.3906/kim-1107-19

• N-isocyaniminotriphenylphosphorane
• aromatic carboxylic acid
• aromatic bis-aldehydes
• 1,3,4-oxadiazole
• aza-Wittig reaction
• secondary amine

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.

• 出版日期2012