Synthesis of novel heterocyclic structures via reaction of isocyanides with S-trans-enones.
The reaction of enone 1, bearing an internal nucleophilic moiety, i.e., furan or pyrrole (X = O, NR'), with isocyanides is presented. The formation of products resulting from the reaction of the zwitterionic intermediate 2 with a second equivalent of isocyanide prior to cyclization to give 3, as well as the direct formation of 4 from 2, is described.
Winkler
Jeffrey D
JD
Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104, USA. winkler@sas.upenn.edu
Asselin
Sylvie M
SM
D003486:Cyanides / Q000737:chemistry*; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure
D003486:Cyanides; D006575:Heterocyclic Compounds, 3-Ring; D007659:Ketones