New opportunities with the Duff reaction

J Org Chem. 2008 Aug 1;73(15):5989-92. doi: 10.1021/jo800700b. Epub 2008 Jul 3.

Abstract

The Duff reaction (HMTA, AcOH or TFA) was studied on substituted [6 + 5] heterocyclic compounds. This reaction provides a useful route to aldehydes for compounds bearing sensitive amide functions. It gives also access to tricyclic lactams of potential biological interest. The formation of an aminomethyl intermediate in the Duff reaction mechanism is unequivocally demonstrated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Heterocyclic Compounds / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure

Substances

  • Heterocyclic Compounds