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

DOI

10.3906/kim-1102-3

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

First Page

179

Last Page

188

Recommended Citation

HOLAGH, MOHSEN VALIZADEH; MAHARRAMV, ABEL MOHAMMADALI OGLU; ALLAHVERDIYEV, MIRZA ALIAKBAR OGLU; RAMAZANI, ALI; AHMADI, YAVAR; and SOULDOZI, ALI (2012) "One-pot synthesis of fully substituted 1,3,4-oxadiazole derivatives from aromatic carboxylic acids, cyclobutanone and N-isocyaniminotriphenylphosphorane," Turkish Journal of Chemistry: Vol. 36: No. 1, Article 14. https://doi.org/10.3906/kim-1102-3
Available at: https://journals.tubitak.gov.tr/chem/vol36/iss1/14