Published Online: 15 SEP 2010
Copyright © 2010 John Wiley & Sons, Inc. All rights reserved.
Comprehensive Organic Name Reactions and Reagents
How to Cite
2010. Aza-Claisen Rearrangement. Comprehensive Organic Name Reactions and Reagents. 29:123–127.
- Published Online: 15 SEP 2010
Choose one or more boxes to highlight terms.
In the aza-Claisen rearrangement cleavage of one bond and the formation of a new bond take place. However, in this reaction, one allyl carbon atom is displaced by a nitrogen atom and the carbon-nitrogen bond is the bond to break. The nitrogen atom in aza-Claisen rearrangement has been reported either in a heterocycle or a quaternary amine (ammonium salt). The extension of heterocycle ring or cleavage of ammonium salt has been found to be the important factor which drive this reaction. The reaction between N-methylpyrrole and dimethyl acetylenedicarboxylate (DMAD) is one of the earliest reaction of of the aza-Claisen rearrangement. This reaction has wide application for the synthesis of variety types of nitrogen-containing compounds
- dimethyl acetylenedicarboxylate (DMAD);
- nitrogen-containing heterocycle;