Issue 73, 2014

Improved microwave synthesis of unsymmetrical N,N'-diaryl-1,2-aminoethane and imidazolidinium salts as precursors of N-heterocyclic carbenes

Abstract

Lithium aluminium hydride reduction of bis-unsymmetric-diaryloxamides 3 is difficult to accomplish especially for the sterically hindered mesityl derivative. Using microwaves LAH reduction of 3a,d was successful in a short time, however, with cleavage of the ether linkage to give compounds 11a,d. Extension of this method enabled the reduction of bis-oxamide derivatives 13 to the corresponding tetraamine derivative 14 which was then converted to the bis-imidazolidinium salt 15. Application of this method led to rapid reduction of unsymmetric N,N'-diaryloxamides 16 to the corresponding N,N'-diarylethylenediamines 17 which were converted to their corresponding imidazolidinium salts 18.

Graphical abstract: Improved microwave synthesis of unsymmetrical N,N'-diaryl-1,2-aminoethane and imidazolidinium salts as precursors of N-heterocyclic carbenes

Supplementary files

Article information

Article type
Paper
Submitted
23 Jun 2014
Accepted
18 Aug 2014
First published
18 Aug 2014

RSC Adv., 2014,4, 38869-38876

Author version available

Improved microwave synthesis of unsymmetrical N,N'-diaryl-1,2-aminoethane and imidazolidinium salts as precursors of N-heterocyclic carbenes

Y. A. Ibrahim, N. A. Al-Awadi, T. F. Al-Azemi and E. John, RSC Adv., 2014, 4, 38869 DOI: 10.1039/C4RA06128D

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