Glyoxylic acid and MP-glyoxylate: efficient formaldehyde equivalents in the 3-CC of 2-aminoazines, aldehydes, and isonitriles

Org Lett. 2004 Dec 23;6(26):4989-92. doi: 10.1021/ol0478234.

Abstract

[reaction: see text] Glyoxylic acid, either in solution or immobilized on MP-carbonate (MP-glyoxylate), participates in an uncatalyzed 3-CC with 2-aminoazines and isonitriles to afford novel 2-unsubstituted-3-amino-imidazoheterocycles. MP-glyoxylate serves as a particularly efficient and experimentally convenient formaldehyde equivalent and readily liberates products through decarboxylation/self-release from the resin. These examples furthermore constitute the first application in which MP-CO3 serves as a solid support for transformations involving carboxylic acids.

MeSH terms

  • Aldehydes / chemistry*
  • Azoles / chemistry*
  • Cyclization
  • Glyoxylates / chemistry*
  • Imidazoles / chemical synthesis*
  • Imidazoles / chemistry
  • Molecular Structure
  • Nitriles / chemistry*

Substances

  • Aldehydes
  • Azoles
  • Glyoxylates
  • Imidazoles
  • Nitriles
  • glyoxylic acid