Synthesis of functionalized 5-imino-2,5-dihydro-furans through the reaction of isocyanides with activated acetylenes in the presence of ethyl bromopyruvate

Mol Divers. 2006 Aug;10(3):479-82. doi: 10.1007/s11030-006-9034-4. Epub 2006 Sep 12.

Abstract

The reaction between alkyl(aryl) isocyanides and dibenzoylacetylene in the presence of ethyl bromopyruvate leads to ethyl 3,4-dibenzoyl-2-bromomethyl-5-alkyl(aryl)imino-2,5-dihydro-furan-2-carboxylates in high yields. Dialkyl acetylenedicarboxylates react with tert-butyl isocyanide and ethyl bromopyruvate to produce 3,4-dialkyl 2-ethyl 2-bromomethyl-5-tert-butylimino-2,5-dihydro-furan-2,3,4-tricarboxylates.

MeSH terms

  • Alkynes / chemistry*
  • Cyanides / chemistry*
  • Cyclization
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Molecular Structure
  • Pyruvates / chemistry
  • Pyruvic Acid / chemistry

Substances

  • Alkynes
  • Cyanides
  • Furans
  • Pyruvates
  • bromopyruvate
  • Pyruvic Acid