Bicyclic Amidine-Triggered Cyclization of o-Alkynylisocyanobenzenes: Synthesis of Lactam-Derived Quinolines

J Org Chem. 2023 Jul 7;88(13):8379-8386. doi: 10.1021/acs.joc.3c00405. Epub 2023 Jun 13.

Abstract

Efficient access to the synthesis of lactam-derived quinoline through a bicyclic amidine-triggered cyclization reaction from readily prepared o-alkynylisocyanobenzenes has been developed. The reaction was initiated by nucleophilic attack of the bicyclic amidines to o-alkynylisocyanobenzenes, subsequently with intramolecular cyclization to produce a DBU-quinoline-based amidinium salt, followed by hydrolysis to afford the lactam-derived quinoline in moderate to good yields.

MeSH terms

  • Amidines
  • Cyclization
  • Hydrolysis
  • Lactams*
  • Quinolines*

Substances

  • Lactams
  • Quinolines
  • Amidines