Fischer indole synthesis in low melting mixtures

Org Lett. 2012 Sep 7;14(17):4568-71. doi: 10.1021/ol302034r. Epub 2012 Aug 20.

Abstract

Functionalized indoles are synthezised under mild conditions in a tartaric acid-dimethylurea melt. The melt serves as the solvent and as the catalyst. Under these reaction conditions, sensitive functional groups such as N-Boc, N-Cbz, or azides are stable, and indolenines are obtained regioselectively in excellent yields. The practical use of the method is demonstrated in the synthesis of the hormone melatonin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Chemistry, Organic / methods
  • Combinatorial Chemistry Techniques
  • Heterocyclic Compounds, 3-Ring / chemical synthesis*
  • Heterocyclic Compounds, 3-Ring / chemistry
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Heterocyclic Compounds, 3-Ring
  • Indoles