ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

A metal-free approach for in situ regioselective synthesis of isoxazoles via 1,3 dipolar cycloaddition reaction of nitrile oxide with propargyl bromide

Rajeshwar Reddy Aleti, Srinivasulu Cherukupalli, Sanjeev Dhawan, Vishal Kumar, Pankaj S. Girase, Sachin Mohite, and Rajshekhar Karpoormath

Department of Pharmaceutical Chemistry, College of Health Sciences, University of KwaZulu-Natal, Durban, South Africa

E-mail: karpoormath@ukzn.ac.za

Received: 8 August 2021  Accepted: 4 December 2021

Abstract:

Herein, we report a multi-component reaction (MCRs) to synthesise a range of 3-phenyl-5-(bromomethyl)isoxazoles analogues using DMF/water mixture as solvent, providing desired products in good to excellent yields. The reaction efficiently involves the 1,3-dipolar cycloaddition reaction between propargyl bromide and in situ-generated α-chloro aldoximes. The protocol proceeded well under mild metal-free conditions and showed a tolerance for a wide range of substituents.

Graphical abstract

Keywords: Isoxazole; Propargyl bromide; Metal-free; 1,3-dipolar cycloaddition; α-chloro aldoximes

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-021-02009-8

Chemical Papers 76 (5) 3005–3010 (2022)