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Molecules 2016, 21(5), 660; doi:10.3390/molecules21050660

Synthetic Strategies for 5- and 6-Membered Ring Azaheterocycles Facilitated by Iminyl Radicals

University of St. Andrews, EaStCHEM School of Chemistry, St. Andrews, Fife KY16 9ST, UK
Academic Editor: Fawaz Aldabbagh
Received: 5 April 2016 / Revised: 11 May 2016 / Accepted: 16 May 2016 / Published: 18 May 2016
(This article belongs to the Special Issue Free Radicals in Organic Synthesis)

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. View Full-Text
Keywords: organic synthesis; radicals; heterocycles; photoredox catalysis; natural products organic synthesis; radicals; heterocycles; photoredox catalysis; natural products
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Walton, J.C. Synthetic Strategies for 5- and 6-Membered Ring Azaheterocycles Facilitated by Iminyl Radicals. Molecules 2016, 21, 660.

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