ZnCl2-Promoted Intramolecular Hetero-Diels-Alder Reaction of o-Alkynylphenylcarbodiimides for Synthesis of Dihydrodibenzo[b,g][1,8]naphthyridines

Chem Pharm Bull (Tokyo). 2016 Sep 1;64(9):1364-9. doi: 10.1248/cpb.c16-00363. Epub 2016 Jun 16.

Abstract

The ZnCl2-promoted intramolecular hetero-Diels-Alder reaction of N-(ortho-propargylphenyl)-N'-arylcarbodiimides, in which the aryl-N=C moiety functioned as a 2-azabuta-1,3-diene, 4π component, has been achieved. By this method, very rare 5,12-dihydrodibenzo[b,g][1,8]naphthyridines and fully aromatized dibenzo[b,g][1,8]naphthyridines were successfully synthesized.

MeSH terms

  • Alkynes / chemistry*
  • Chlorides / chemistry*
  • Cycloaddition Reaction
  • Imides / chemistry*
  • Molecular Structure
  • Naphthyridines / chemical synthesis*
  • Naphthyridines / chemistry
  • Zinc Compounds / chemistry*

Substances

  • Alkynes
  • Chlorides
  • Imides
  • Naphthyridines
  • Zinc Compounds
  • dihydrodibenzo(b,g)(1,8)naphthyridine
  • zinc chloride