1,3-dipolar cycloadditions from tricyclic hemiaminals. Synthesis of the quinocarcin core through catalyst-free generation of azomethine ylides

Org Biomol Chem. 2011 Sep 21;9(18):6271-7. doi: 10.1039/c1ob05181d. Epub 2011 Jul 19.

Abstract

The generation of azomethine ylides from the readily accessible hemiaminals 3 and 8 or from iminium salt 10 was studied. Compounds 8 gave anti- and syn-cycloadducts containing the quinocarcin core through a catalyst-free dehydration process.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Azo Compounds / chemical synthesis*
  • Azo Compounds / chemistry
  • Cyclization
  • Imines / chemistry
  • Isoquinolines / chemical synthesis*
  • Isoquinolines / chemistry
  • Thiosemicarbazones / chemical synthesis*
  • Thiosemicarbazones / chemistry

Substances

  • Amines
  • Azo Compounds
  • Imines
  • Isoquinolines
  • Thiosemicarbazones
  • azomethine
  • quinocarcin