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

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Synthetic strategies for 5- and 6-membered ring azaheterocycles facilitated by iminyl radicals. / Walton, John Christopher.

In: Molecules, Vol. 21, No. 5, 18.05.2016.

Research output: Contribution to journalReview article

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Walton, JC 2016, 'Synthetic strategies for 5- and 6-membered ring azaheterocycles facilitated by iminyl radicals' Molecules, vol 21, no. 5. DOI: 10.3390/molecules21050660

APA

Walton, J. C. (2016). Synthetic strategies for 5- and 6-membered ring azaheterocycles facilitated by iminyl radicals. Molecules, 21(5). DOI: 10.3390/molecules21050660

Vancouver

Walton JC. Synthetic strategies for 5- and 6-membered ring azaheterocycles facilitated by iminyl radicals. Molecules. 2016 May 18;21(5). Available from, DOI: 10.3390/molecules21050660

Author

Walton, John Christopher / Synthetic strategies for 5- and 6-membered ring azaheterocycles facilitated by iminyl radicals.

In: Molecules, Vol. 21, No. 5, 18.05.2016.

Research output: Contribution to journalReview article

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@article{f27b4fda158e4776a5be3795539c5085,
title = "Synthetic strategies for 5- and 6-membered ring azaheterocycles facilitated by iminyl radicals",
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.",
keywords = "Organic synthesis, Radicals, Hetercycles, Photoredox catalysis, Natural products",
author = "Walton, {John Christopher}",
note = "The author thanks EaStCHEM for financial support.",
year = "2016",
month = "5",
doi = "10.3390/molecules21050660",
volume = "21",
journal = "Molecules",
issn = "1420-3049",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "5",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - Synthetic strategies for 5- and 6-membered ring azaheterocycles facilitated by iminyl radicals

AU - Walton,John Christopher

N1 - The author thanks EaStCHEM for financial support.

PY - 2016/5/18

Y1 - 2016/5/18

N2 - 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.

AB - 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.

KW - Organic synthesis

KW - Radicals

KW - Hetercycles

KW - Photoredox catalysis

KW - Natural products

U2 - 10.3390/molecules21050660

DO - 10.3390/molecules21050660

M3 - Review article

VL - 21

JO - Molecules

T2 - Molecules

JF - Molecules

SN - 1420-3049

IS - 5

ER -

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ID: 242607988