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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 32, Number 8
BKCSDE 32(8)
August 20, 2011 

Preparation of Fully Substituted 1,3,4-Oxadiazole Derivatives from N-Isocyaniminotriphenylphosphorane, (E)-Cinnamic Acids, Chloroacetone and Primary Amines
Ali Ramazani*, Fatemeh Zeinali Nasrabadi, Zahra Karimi, Morteza Rouhani
N-Isocyaniminotriphenylphosphorane, Chloroacetone, (E)-Cinnamic acid, 1,3,4-Oxadiazole, aza-Wittig reaction
The 1:1 imine intermediate generated by the addition of primary amine to chloroacetone is trapped by Nisocyaniminotriphenylphosphorane in the presence of (E)-cinnamic acids and the corresponding iminophosphorane intermediate was formed. 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.
2700 - 2704
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