Highly selective domino multicyclizations for forming polycyclic fused acridines and azaheterocyclic skeletons

Org Lett. 2013 Apr 5;15(7):1540-3. doi: 10.1021/ol400322v. Epub 2013 Mar 18.

Abstract

Highly selective four-component domino multicyclizations for the synthesis of new fused acridines and azaheterocyclic skeletons have been established by mixing common reactants in isobutyric acid under microwave irradiation. The reactions proceeded at fast rates and were conducted to completion within 20-30 min. Up to seven new chemical bonds, four rings, and four stereocenters were assembled in a convenient one-pot operation. The resulting hexacyclic and pentacyclic fused acridines and their stereochemistry have been fully characterized and determined by X-ray structural analysis.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acridines / chemical synthesis*
  • Acridines / chemistry
  • Crystallography, X-Ray
  • Cyclization
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Microwaves
  • Molecular Structure
  • Stereoisomerism

Substances

  • Acridines
  • Heterocyclic Compounds, 4 or More Rings