Development of a DABCO-Succinic Acid Based Catalytic System for the Aza-Michael Addition and Aza-Michael/Knoevenagel Tandem Reaction of Thiazolidine-2,4-dione to Electron Deficient Alkenes

J Org Chem. 2021 Dec 3;86(23):16785-16794. doi: 10.1021/acs.joc.1c02003. Epub 2021 Nov 10.

Abstract

A DABCO catalyzed aza-Michael addition of thiazolidine-2,4-dione to a variety of electron deficient alkenes has been developed. Additionally, a DABCO/succinic acid salt system has been designed that allows for the one pot tandem aza-Michael/Knoevenagel reaction of thiazolidine-2,4-dione to give difunctionalized thiazolidine-2,4-dione products. To the best of our knowledge, this is the first example of a one-pot tandem aza-Michael/Knoevenagel reaction involving thiazolidine-2,4-dione.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes*
  • Catalysis
  • Electrons
  • Molecular Structure
  • Piperazines
  • Succinic Acid*
  • Thiazolidinediones
  • Thiazolidines

Substances

  • Alkenes
  • Piperazines
  • Thiazolidinediones
  • Thiazolidines
  • thiazolidine-2,4-dione
  • Succinic Acid
  • triethylenediamine