An improved synthesis of pyran-3,5-dione: application to the synthesis of ABT-598, a potassium channel opener, via Hantzsch reaction

J Org Chem. 2006 Feb 17;71(4):1725-7. doi: 10.1021/jo052226w.

Abstract

Ketoester 1 is cyclized to give pyran-3,5-dione 2 in 78% yield using a parallel addition of ketoester 1 and base NaO(t)Bu in refluxing THF. Compared to the previously reported procedures, these optimized conditions have significantly increased the yield of this transformation and the quality of pyran 2 and prove to be suitable for large-scale preparation. An application of 2 to the synthesis of ABT-598, a potassium channel opener, is demonstrated.

MeSH terms

  • Cyclization
  • Esters / chemistry
  • Potassium Channels / agonists*
  • Pyrans / chemical synthesis*
  • Pyrones / chemical synthesis*
  • tert-Butyl Alcohol

Substances

  • Esters
  • Potassium Channels
  • Pyrans
  • Pyrones
  • tert-Butyl Alcohol