Synthesis of novel β-aminocyclobutanecarboxylic acid derivatives by a solvent-free aza-Michael addition and subsequent ring closure

Org Biomol Chem. 2011 Oct 21;9(20):7085-91. doi: 10.1039/c1ob05872j. Epub 2011 Aug 24.

Abstract

Novel β-aminocyclobutanecarboxylic acid derivatives were prepared via a sequential solvent-free aza-Michael addition of benzophenone imine across 3-halopropylidenemalonates and base-induced ring closure. These highly substituted cyclobutanedicarboxylic acid derivatives were subjected to a reactivity study which demonstrated the tendency of these donor-acceptor substituted four-membered rings to be converted into their corresponding ring-opened products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aza Compounds / chemistry*
  • Carboxylic Acids / chemical synthesis*
  • Cyclobutanes / chemical synthesis*
  • Molecular Structure

Substances

  • 2-aminocyclobutanecarboxylic acid
  • Aza Compounds
  • Carboxylic Acids
  • Cyclobutanes