New three-component reaction: novel formation of a seven-membered ring by the unexpected reaction at the gamma-position of the beta-keto ester

Org Lett. 2007 Apr 26;9(9):1687-90. doi: 10.1021/ol070402c. Epub 2007 Apr 5.

Abstract

[reaction: see text] The novel three-component reaction of aromatic aldehydes, ethylenediamine, and beta-keto esters is described. In this reaction, beta-keto esters react at the gamma-position which is generally unreactive to produce the seven-membered ring compounds. Products have secondary amines and beta-enamino esters, which can serve in further functionalizations to produce molecular diversity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Crystallography, X-Ray
  • Esters / chemical synthesis
  • Esters / chemistry*
  • Models, Molecular
  • Molecular Structure

Substances

  • Aldehydes
  • Esters