Efficient preparation of 2-indolyl-1-nitroalkane derivatives employing nitroalkenes as versatile Michael acceptors: new practical linear approach to alkyl 9h-beta-carboline-4-carboxylate

J Org Chem. 2005 Mar 4;70(5):1941-4. doi: 10.1021/jo048776w.

Abstract

The combination of cerium(III) chloride heptahydrate and sodium iodide supported on silica gel is known to promote Michael-type additions. Continuing our work on solvent-free conditions, the CeCl3.7H2O-NaI-SiO2 system catalyzes the addition of a variety of indoles and nitroalkenes, giving 2-indolyl-1-nitroalkane derivatives in good yields. Development of this method has resulted in a new protocol for the synthesis of 4-substituted beta-carbolines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkanes / chemical synthesis*
  • Alkenes / chemistry*
  • Carbolines / chemical synthesis*
  • Carboxylic Acids / chemical synthesis*
  • Molecular Structure
  • Nitro Compounds / chemical synthesis*

Substances

  • Alkanes
  • Alkenes
  • Carbolines
  • Carboxylic Acids
  • Nitro Compounds