Reactions of enaminones with diazocarbonyl compounds


Gungor F. Ş. , HANCIOGLU N., Anac O.

Helvetica Chimica Acta, cilt.96, sa.3, ss.488-493, 2013 (SCI Expanded İndekslerine Giren Dergi) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 96 Konu: 3
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1002/hlca.201200233
  • Dergi Adı: Helvetica Chimica Acta
  • Sayfa Sayıları: ss.488-493

Özet

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.