Addition of benzylic and allylic organozinc and Grignard reagents to resin-bound imines to provide alpha-branched secondary amines bearing a wide variety of functional groups. Utility in the synthesis of beta-3 adrenergic receptor agonists

J Comb Chem. 2005 Jan-Feb;7(1):99-108. doi: 10.1021/cc0498682.

Abstract

Benzylic and allylic organozinc and Grignard reagents have been added to resin-bound imines to provide alpha-branched secondary amines. Many functional groups, including electrophilic groups, were compatible with this methodology. Three modules--a resin-bound primary amine, an aromatic aldehyde, and the organometallic--were independently varied to produce a combinatorial library of alpha-branched secondary amines designed as beta-3 adrenergic receptor agonists.

MeSH terms

  • Adrenergic beta-3 Receptor Agonists*
  • Adrenergic beta-Agonists / chemical synthesis*
  • Adrenergic beta-Agonists / chemistry
  • Amines / chemistry*
  • Benzene / chemistry*
  • Combinatorial Chemistry Techniques
  • Imines / chemistry*
  • Molecular Structure
  • Structure-Activity Relationship
  • Zinc / chemistry*

Substances

  • Adrenergic beta-3 Receptor Agonists
  • Adrenergic beta-Agonists
  • Amines
  • Imines
  • Zinc
  • Benzene