A novel four-component reaction for the synthesis of disubstituted 1,3,4-oxadiazole derivatives.
The 1:1 imine intermediate generated by the addition of benzyl amine to cyclobutanone is trapped by (N-isocyanimino)triphenylphosphorane in the presence of an aromatic carboxylic acid leads to the formation of the corresponding iminophosphorane intermediate. Disubstituted 1,3,4-oxadiazole derivatives are formed via intramolecular aza-Wittig reaction of the iminophosphorane intermediate. The reactions were completed in neutral conditions at room temperature. The disubstituted 1,3,4-oxadiazole derivatives, were produced in excellent yields.
Ramazani
Ali
A
Chemistry Department, Zanjan University, PO Box 45195-313, Zanjan, Iran. aliramazani@gmail.com
Shajari
Nahid
N
Mahyari
Amir
A
Ahmadi
Yavar
Y
D001596:Benzylamines / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D003503:Cyclobutanes / Q000737:chemistry; D010069:Oxadiazoles / Q000138:chemical synthesis*
D001596:Benzylamines; D002264:Carboxylic Acids; D003503:Cyclobutanes; D010069:Oxadiazoles; C553737:cyclobutenone
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