Synthesis of N-alkyl-octahydroisoquinolin-1-one-8-carboxamide libraries using a tandem Diels-Alder/acylation sequence

J Comb Chem. 2007 Nov-Dec;9(6):1188-92. doi: 10.1021/cc700127f. Epub 2007 Sep 27.

Abstract

A synthetic sequence was developed in which a diene containing an attached secondary amine was reacted with maleic anhydride to afford the title structures in one step. The reaction involves a Diels-Alder reaction combined with a transacylation reaction of the imide group. A series of six scaffolds was constructed using this methodology. Each scaffold was subsequently reacted with 12 amines to afford a library containing 72 compounds.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Acylation
  • Alkadienes / chemistry
  • Alkanes / chemical synthesis*
  • Amines / chemistry*
  • Combinatorial Chemistry Techniques*
  • Cyclization
  • Isoquinolines / chemical synthesis*
  • Maleic Anhydrides / chemistry*
  • Models, Chemical
  • Stereoisomerism

Substances

  • Alkadienes
  • Alkanes
  • Amines
  • Isoquinolines
  • Maleic Anhydrides