One-pot synthesis of fully substituted 1,3,4-oxadiazole derivatives from aromatic carboxylic acids, cyclobutanone and N-isocyaniminotriphenylphosphorane

Authors: MOHSEN VALIZADEH HOLAGH, ABEL MOHAMMADALI OGLU MAHARRAMV, MIRZA ALIAKBAR OGLU ALLAHVERDIYEV, ALI RAMAZANI, YAVAR AHMADI, ALI SOULDOZI

Abstract: Reactions of N-isocyaniminotriphenylphosphorane with cyclobutanone in the presence of aromatic (or heteroaromatic) carboxylic acids proceeded smoothly at room temperature and in neutral conditions to afford sterically congested 1-(5-aryl-1,3,4-oxadiazol-2-yl)- 1-cyclobutanol derivatives in high yields. The reaction proceeded smoothly and cleanly under mild conditions and no side reactions were observed. The structures of the products were deduced from their IR, ^1HNMR, and ^{13}CNMR spectra, and mass spectrometry.

Keywords: N-isocyaniminotriphenylphosphorane, intramolecular aza-Wittig reaction, 1,3,4-oxadiazole, aromatic carboxylic acid, cyclobutanone

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