Synthetic strategies for 5- and 6-membered ring azaheterocycles facilitated by iminyl radicals

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Abstract

The totality of chemical space is so immense that only a small fraction can ever be explored. Computational searching has indicated that bioactivity is associated with a comparatively small number of ring-containing structures. Pyrrole, indole, pyridine, quinoline, quinazoline and related 6-membered ring-containing aza-arenes figure prominently. This review focuses on the search for fast, efficient and environmentally friendly preparative methods for these rings with specific emphasis on iminyl radical mediated procedures. Oxime derivatives, particularly oxime esters and oxime ethers, are attractive precursors for these radicals. Their use is described in conventional thermolytic, microwave-assisted and UV-vis based preparative procedures. Photoredox catalyzed protocols involving designer oxime ethers are also covered. Choice can be made amongst these synthetic strategies for a wide variety of 5- and 6-membered ring heterocycles including phenanthridine and related aza-arenes. Applications to selected natural products and bioactive molecules including trispheridine, vasconine, luotonin A and rutaecarpine are included.
Original languageEnglish
JournalMolecules
Volume21
Issue number5
DOIs
Publication statusPublished - 18 May 2016

Keywords

  • Organic synthesis
  • Radicals
  • Hetercycles
  • Photoredox catalysis
  • Natural products

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