A new route to meso-formyl porphyrins

J Org Chem. 2004 Jul 23;69(15):5112-5. doi: 10.1021/jo049819b.

Abstract

Prior syntheses of porphyrins bearing meso-formyl groups have generally employed the Vilsmeier formylation of an acid-resistant copper or nickel porphyrin. A new approach for the synthesis of free base porphyrins bearing one or two (cis or trans) meso-formyl substituents entails the use of a dipyrromethane bearing an acetal group at the 5-position, a dipyrromethane-1-carbinol bearing an acetal group at the 5-position or carbinol position, or a dipyrromethane-1,9-dicarbinol bearing an acetal group at a carbinol position. Treatment of the resulting meso-acetal-substituted free base porphyrin to gentle acidic hydrolysis yields the corresponding meso-formyl porphyrin.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Copper / chemistry
  • Molecular Structure
  • Nickel / chemistry
  • Porphyrins / chemical synthesis*
  • Porphyrins / chemistry

Substances

  • Porphyrins
  • Copper
  • Nickel