A highly efficient biomimetic aromatization of Hantzsch-1,4-dihydropyridines with t-butylhydroperoxide, catalysed by iron(III) phthalocyanine chloride

Bioorg Med Chem. 2008 Oct 15;16(20):9276-82. doi: 10.1016/j.bmc.2008.09.004. Epub 2008 Sep 5.

Abstract

Rapid aromatization of Hantzsch-1,4-DHPs with t-butylhydroperoxide catalysed by iron(III) phthalocyanine chloride is described. The reaction proceeds smoothly at room temperature within 1-35 min and the products of high purity were isolated in excellent yields. To explain the reactivity of this catalytical system plausible mechanism have been proposed to involve formation of high-valent oxoferryl species as in cytochrome P450 itself.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biomimetic Materials / chemistry*
  • Catalysis
  • Chlorides / chemistry*
  • Dihydropyridines / chemistry*
  • Indoles / chemistry*
  • Iron Compounds / chemistry*
  • Isoindoles
  • Molecular Structure
  • Oxidants / chemistry
  • Oxidation-Reduction
  • Solvents
  • tert-Butylhydroperoxide / chemistry*

Substances

  • Chlorides
  • Dihydropyridines
  • Indoles
  • Iron Compounds
  • Isoindoles
  • Oxidants
  • Solvents
  • 1,4-dihydropyridine
  • tert-Butylhydroperoxide
  • phthalocyanine