Synthetic Potential of Regio- and Stereoselective Ring Expansion Reactions of Six-Membered Carbo- and Heterocyclic Ring Systems: A Review

Int J Mol Sci. 2023 Apr 3;24(7):6692. doi: 10.3390/ijms24076692.

Abstract

Ring expansion reactions fascinate synthetic chemists owing to their importance in synthesizing biologically active compounds and their efficacy in medicinal chemistry. The present review summarizes a number of synthetic methodologies, including stereoselective and regioselective pathways adopted by scientists, for framing medium- to large-size carbo- and heterocycles involving lactams, lactone, azepine and azulene derivatives via ring expansion of six-membered carbo- and heterocycles that have been reported from 2007-2022. Numerous rearrangement and cycloaddition reactions involving Tiffeneau-Demjanov rearrangement, Aza-Claisen rearrangement, Schmidt rearrangement, Beckmann rearrangement, etc., have been described in this regard.

Keywords: azepine; azulene; biological activities; heterocyclic ring expansion; six-member rings.

Publication types

  • Review

MeSH terms

  • Chemistry, Pharmaceutical
  • Cyclization
  • Cycloaddition Reaction
  • Heterocyclic Compounds* / chemistry
  • Lactams*

Substances

  • Lactams
  • Heterocyclic Compounds