Barton esters for initiator-free radical cyclisation with heteroaromatic substitution

Robert Coyle; Karen Fahey; Fawaz Aldabbagh

doi:10.1039/c3ob27313j

Barton esters for initiator-free radical cyclisation with heteroaromatic substitution

Robert Coyle, Karen Fahey, Fawaz Aldabbagh

National University of Ireland, Galway

Research output: Contribution to journal › Article › peer-review

19 Citations (Scopus)

Abstract

S-(1-Oxido-2-pyridinyl)-1,1,3,3-tetramethylthiouronium hexafluorophosphate (HOTT) facilitates the first examples of efficient radical cyclisation with (hetero)aromatic substitution via Barton ester intermediates. Cyclopropyl and alkyl radicals allow access to five, six and seven-membered alicyclic-ring fused heterocycles with and without an additional fused cyclopropane, including the skeleton of the anti-cancer agent, cyclopropamitosene, expanded, and diazole analogues. Radical initiators are not required for cyclisation from carboxylic acid precursors.

Original language	English
Pages (from-to)	1672-1682
Number of pages	11
Journal	Organic and Biomolecular Chemistry
Volume	11
Issue number	10
DOIs	https://doi.org/10.1039/c3ob27313j
Publication status	Published - 14 Mar 2013
Externally published	Yes

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abstract = "S-(1-Oxido-2-pyridinyl)-1,1,3,3-tetramethylthiouronium hexafluorophosphate (HOTT) facilitates the first examples of efficient radical cyclisation with (hetero)aromatic substitution via Barton ester intermediates. Cyclopropyl and alkyl radicals allow access to five, six and seven-membered alicyclic-ring fused heterocycles with and without an additional fused cyclopropane, including the skeleton of the anti-cancer agent, cyclopropamitosene, expanded, and diazole analogues. Radical initiators are not required for cyclisation from carboxylic acid precursors.",

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AU - Fahey, Karen

AU - Aldabbagh, Fawaz

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N2 - S-(1-Oxido-2-pyridinyl)-1,1,3,3-tetramethylthiouronium hexafluorophosphate (HOTT) facilitates the first examples of efficient radical cyclisation with (hetero)aromatic substitution via Barton ester intermediates. Cyclopropyl and alkyl radicals allow access to five, six and seven-membered alicyclic-ring fused heterocycles with and without an additional fused cyclopropane, including the skeleton of the anti-cancer agent, cyclopropamitosene, expanded, and diazole analogues. Radical initiators are not required for cyclisation from carboxylic acid precursors.

AB - S-(1-Oxido-2-pyridinyl)-1,1,3,3-tetramethylthiouronium hexafluorophosphate (HOTT) facilitates the first examples of efficient radical cyclisation with (hetero)aromatic substitution via Barton ester intermediates. Cyclopropyl and alkyl radicals allow access to five, six and seven-membered alicyclic-ring fused heterocycles with and without an additional fused cyclopropane, including the skeleton of the anti-cancer agent, cyclopropamitosene, expanded, and diazole analogues. Radical initiators are not required for cyclisation from carboxylic acid precursors.

UR - https://www.scopus.com/pages/publications/84874044708

U2 - 10.1039/c3ob27313j

DO - 10.1039/c3ob27313j

M3 - Article

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AN - SCOPUS:84874044708

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JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 10

ER -

Barton esters for initiator-free radical cyclisation with heteroaromatic substitution

Abstract

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