Benzoic Acid Catalyzed Annulations of α-Amino Acids and Aromatic Aldehydes Containing an ortho-Michael Acceptor: Access to 2,5-Dihydro-1H-benzo[c]azepines and 10,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a]azepines

Org Lett. 2015 Nov 6;17(21):5180-3. doi: 10.1021/acs.orglett.5b02484. Epub 2015 Oct 21.

Abstract

A novel one-pot efficient synthesis of 2,5-dihydro-1H-benzo[c]azepines and 10,11-dihydro-5H-benzo[e]pyrrolo[1,2-a]azepines from α-amino acids and aromatic aldehydes containing an ortho-Michael acceptor is reported via decarboxylative annulations without metal catalysts in yields of 52-91%. Under microwave irradiation, this protocol provides rapid access to polycyclic ring systems (only 5 min in most cases).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Amino Acids / chemistry*
  • Azepines / chemistry*
  • Benzoic Acid / chemistry*
  • Catalysis
  • Microwaves
  • Molecular Structure
  • Stereoisomerism

Substances

  • Aldehydes
  • Amino Acids
  • Azepines
  • Benzoic Acid