Scaffold-directed and traceless synthesis of tricyclic quinoxalinone imidazoles under microwave irradiation: for SCS-09 special issue-combinatorial approaches to drug discovery

Mol Divers. 2011 Feb;15(1):101-7. doi: 10.1007/s11030-010-9244-7. Epub 2010 Mar 20.

Abstract

Traceless synthesis of 2-aminoimidazoquinoxalinones has been performed on soluble polymer support under open-vessel microwave dielectric heating. The reaction progression is monitored directly by the conventional proton NMR which indicated no release of the substrate from the support. Fmoc-deprotected amino acid polymer conjugates react with 1,5-difluoro-2,4-dinitro benzene to yield polymer bound dinitro fluoro amines, which are further substituted by various primary amines to yield PEG-immobilized dinitrodiamines. Simultaneous reduction of aromatic meta-dinitro group leads to the traceless release of 2-quinoxalinones, followed by N-hetero cyclization with various isothiocyanates in the presence of mercury(II)chloride to furnish 2-aminoimidazoquinolinone rings with three points of diversity at rapid pace.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Combinatorial Chemistry Techniques / methods*
  • Cyclization
  • Dinitrofluorobenzene / analogs & derivatives
  • Dinitrofluorobenzene / chemistry
  • Drug Discovery / methods*
  • Imidazoles / chemical synthesis*
  • Imidazoles / chemistry*
  • Microwaves*
  • Small Molecule Libraries / chemical synthesis
  • Small Molecule Libraries / chemistry

Substances

  • Imidazoles
  • Small Molecule Libraries
  • Dinitrofluorobenzene
  • 1,5-difluoro-2,4-dinitrobenzene