Base-promoted annulation of α-hydroxy ketones and dimethyl but-2-ynedioate: straightforward access to pyrano[4,3-a]quinolizine-1,4,6(2H)-triones and 2H-pyran-2,5(6H)-diones

Org Biomol Chem. 2014 Nov 7;12(41):8128-31. doi: 10.1039/c4ob01858c. Epub 2014 Sep 18.

Abstract

A novel and efficient cascade annulation of tertiary α-hydroxy ketones and dimethyl but-2-ynedioate is reported. The reaction, which only requires a base as the promoter, provides a straightforward access to polysubstituted pyrano[4,3-a]quinolizine-1,4,6(2H)-triones and 2H-pyran-2,5(6H)-diones under very mild reaction conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemical synthesis*
  • Alkynes / chemistry
  • Crystallography, X-Ray
  • Dicarboxylic Acids / chemistry*
  • Ketones / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Pyrones / chemical synthesis*
  • Pyrones / chemistry
  • Quinolizines / chemistry*

Substances

  • Alkynes
  • Dicarboxylic Acids
  • Ketones
  • Pyrones
  • Quinolizines