Reactions of enaminones with diazocarbonyl compounds


Gungor F. Ş. , HANCIOGLU N., Anac O.

Helvetica Chimica Acta, vol.96, no.3, pp.488-493, 2013 (Journal Indexed in SCI Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 96 Issue: 3
  • Publication Date: 2013
  • Doi Number: 10.1002/hlca.201200233
  • Title of Journal : Helvetica Chimica Acta
  • Page Numbers: pp.488-493

Abstract

The [Cu(acac)2]-catalyzed reactions of several tertiary enaminones with three diazocarbonyl compounds, i.e., dimethyl diazomalonate, ethyl diazoacetoacetate, and ethyl diazoacetate, yielded amino- and additionally carbonyl-substituted dihydrofurans, together with further furan derivatives. Due to the conjugation of α-carbonyl/α-Ph groups, reactions proceeded only via 1,5-electrocyclization of corresponding keto-ylides. On the other hand, in the absence of any α-substituent, tertiary enaminone and ethyl diazoacetate, reacted via an accompanying mechanism by a push-pull cyclopropane intermediate, to yield a 2,4-dicarbonyl-substituted furan in one step with moderate yield. Copyright © 2013 Verlag Helvetica Chimica Acta AG, Zürich, Switzerland.