Turkish Journal of Chemistry, Vol.36, No.1, 179-188, 2012
One-pot synthesis of fully substituted 1,3,4-oxadiazole derivatives from aromatic carboxylic acids, cyclobutanone and N-isocyaniminotriphenylphosphorane
Reactions of N-isocyaniminotriphenylphosphorane with cyclobutamone 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, (HNMR)-H-1, and (CNMR)-C-13 spectra, and mass spectrometry.
Keywords:N-isocyaniminotriphenylphosphorane;intramolecular aza-Wittig reaction;1,3,4-oxadiazole;aromatic carboxylic acid;cyclobutanone