Preparation of 1,5-methano-2,3,4,5- tetrahydro-1H-3-benzazepine via Pd-catalyzed cyclization

Org Lett. 2004 Jul 8;6(14):2357-60. doi: 10.1021/ol049316s.

Abstract

[reaction: see text] A new approach to prepare 1,5-methano-2,3,4,5-tetrahydro-1H-3-benzanepine (1) is discussed. This strategy utilized a tandem Michael addition and Pd-catalyzed cyclization to afford cyanobenzofulvene acetal 13. This indene intermediate (13) was subjected to hydrogenolysis to provide an amino ester (12) and was cyclized with base to afford lactam 5. The lactam (5) was reduced with borane to afford the desired benzazepine (1).

MeSH terms

  • Benzazepines / chemical synthesis*
  • Catalysis
  • Combinatorial Chemistry Techniques*
  • Cyclization
  • Indicators and Reagents
  • Lactams / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemical synthesis*
  • Molecular Structure
  • Palladium / chemistry*

Substances

  • Benzazepines
  • Indicators and Reagents
  • Lactams
  • Palladium
  • Methane