Document Type : Original Research Article

Authors

• Hamideh Javanbani ¹
• Ali Ramazani ²
• Sang Woo Joo ³
• Yavar Ahmadi ⁴
• Vahid Azizkhani ⁵
• Pegah Azimzadeh Asiabi ⁶

¹ University of Zanjan

² UNIVERSITY OF ZANJAN

³ Yeungnam University

⁴ Young Researchers and Elite Clube, Marand Branch, Islamic Azad University

⁵ Payame Noor University

⁶ Nuclear Science and Technology Research Institute

Abstract

Reactions of N-isocyaniminotriphenylphosphorane with cyclopentanone have been studied in the presence of aromatic carboxylic acids and primary amines, proceeds smoothly at room temperature under neutral conditions to afford sterically congested 1,3,4-oxadiazole derivatives by an intramolecular Aza-Wittig cyclization in CH2Cl2 in excellent yields. The structures of the products were deduced from their IR, Mass, ¹H NMR, and ¹³C NMR spectra. The reaction proceeds smoothly and cleanly under mild conditions and no side reactions were observed. The method offers a mild, simple, and efficient route for the preparation of fully substituted 1,3,4-oxadiazoles from cyclopentanone, primary amines, N-isocyaniminotriphenylphosphorane and aromatic carboxylic acids. Easy work-up, high yields and fairly mild reaction conditions make it a useful procedure in comparison to the modern synthetic methodologies.

Graphical Abstract

Keywords

• N-isocyaniminotriphenylphosphorane
• cyclopentanone
• aromatic carboxylic acids
• primary amines
• oxadiazole

Main Subjects

• Organic chemistry