Polymer-supported stereoselective synthesis of benzimidazolinopiperazinones

J Org Chem. 2012 Jul 6;77(13):5687-95. doi: 10.1021/jo300836c. Epub 2012 Jun 13.

Abstract

We describe the efficient synthesis of 4,7,8,10-tetrasubstituted-(((4S,10aS)-3-oxo-3,4,10,10a-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazin-2(1H)-yl)alkyl)amides on solid phase via tandem N-acyliminium ion cyclization-nucleophilic addition reactions. The synthesis proceeded with complete stereocontrol of a newly formed stereogenic center, provided crude material of high purity, and used commercially available building blocks under mild reaction conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzimidazoles / chemical synthesis*
  • Benzimidazoles / chemistry
  • Cyclization
  • Molecular Structure
  • Piperazines / chemical synthesis*
  • Piperazines / chemistry
  • Polymers / chemistry*
  • Stereoisomerism

Substances

  • Benzimidazoles
  • Piperazines
  • Polymers