Three-Component Synthesis of
Some Novel N-Heterocycle Methyl-O-oxime Ethers

Mohammad Navid Soltani Rad; Somayeh Behrouz; Abdo Reza Nekoei; Zeinab Faghih; Ali Khalafi-Nezhad

doi:10.1055/s-0031-1289599

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Synthesis 2011(24): 4068-4076
DOI: 10.1055/s-0031-1289599

PAPER

Three-Component Synthesis of Some Novel N-Heterocycle Methyl-O-oxime Ethers

Mohammad Navid Soltani Rad*^a, Somayeh Behrouz*^a, Abdo Reza Nekoei^a, Zeinab Faghih^b, Ali Khalafi-Nezhad^b
^a Department of Chemistry, Shiraz University of Technology, Shiraz 71555-313, Iran
Fax: +98(711)7354520; e-Mail: soltani@sutech.ac.ir; e-Mail: behrouz@sutech.ac.ir;
^b Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran

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Publication History

Received 12 August 2011
Publication Date:
09 November 2011 (online)

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Abstract

A convenient and highly efficient protocol for one-pot synthesis of some novel N-heterocycle methyl-O-oxime ethers is described. In this method, three-component coupling of different types of ketoximes, with methylene iodide and nitrogen heterocycles, including imidazoles, benzimidazole, benzotriazole, and theophylline in the presence of an equimolar mixture of K₂CO₃/Et₃N in refluxing MeCN furnished the corresponding N-heterocycle methyl-O-oxime ethers in good yields. This methodology is highly efficient for the synthesis of various structurally diverse N-heterocycle methyl-O-oxime ethers. The results of quantum mechanical studies on reaction intermediates are discussed.

Key words

three-component reaction (3CR) - oxime - O-oxime ether - methylene iodide - N-heterocycle

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