Turkish Journal of Chemistry
Abstract
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.
DOI
10.3906/kim-1107-19
Keywords
N-isocyaniminotriphenylphosphorane, aromatic carboxylic acid, aromatic bis-aldehydes, 1, 3, 4-oxadiazole, aza-Wittig reaction, secondary amine
First Page
81
Last Page
91
Recommended Citation
RAMAZANI, A, KARIMI, Z, SOULDOZI, A, & AHMADI, Y (2012). 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 36 (1): 81-91. https://doi.org/10.3906/kim-1107-19
