Access to Some C5-Cyclised 2-Pyrones and 2-Pyridones via Direct Arylation; Retention of Chloride as a Synthetic Handle

Aisling M. Prendergast; Leticia M. Pardo; Ian J.S. Fairlamb; Gerard P. McGlacken

doi:10.1002/ejoc.201700980

Access to Some C5-Cyclised 2-Pyrones and 2-Pyridones via Direct Arylation; Retention of Chloride as a Synthetic Handle

Aisling M. Prendergast, Leticia M. Pardo, Ian J.S. Fairlamb, Gerard P. McGlacken^*

^*Corresponding author for this work

Chemistry

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

Abstract

The synthetic effort towards the functionalisation of C–H bonds on 2-pyrones and 2-pyridones has been enabled by the preferential reactivity of the C-3 position. Herein, we report a direct arylation protocol for the intramolecular coupling of 2-pyrones and 2-pyridones, allowing access to a previously unavailable class of C-5 cyclised products with an unstudied biological profile. A C–Cl bond was retained at C-3 during the direct arylation process allowing further derivatisation at C-3, using a Suzuki–Miyaura cross-coupling reaction.

Original language	English
Pages (from-to)	5119-5124
Number of pages	6
Journal	European Journal of Organic Chemistry
Volume	2017
Issue number	34
Early online date	11 Sept 2017
DOIs	https://doi.org/10.1002/ejoc.201700980
Publication status	Published - 13 Sept 2017

Bibliographical note

© 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

Keywords

C-H activation
Cross-coupling
Heterocycles
Palladium
Synthetic methods

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10.1002/ejoc.201700980

EJOC_2017_Fairlamb_co_author
© 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.
Accepted author manuscript, 931 KB

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abstract = "The synthetic effort towards the functionalisation of C–H bonds on 2-pyrones and 2-pyridones has been enabled by the preferential reactivity of the C-3 position. Herein, we report a direct arylation protocol for the intramolecular coupling of 2-pyrones and 2-pyridones, allowing access to a previously unavailable class of C-5 cyclised products with an unstudied biological profile. A C–Cl bond was retained at C-3 during the direct arylation process allowing further derivatisation at C-3, using a Suzuki–Miyaura cross-coupling reaction.",

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AU - Pardo, Leticia M.

AU - Fairlamb, Ian J.S.

AU - McGlacken, Gerard P.

N1 - © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

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AB - The synthetic effort towards the functionalisation of C–H bonds on 2-pyrones and 2-pyridones has been enabled by the preferential reactivity of the C-3 position. Herein, we report a direct arylation protocol for the intramolecular coupling of 2-pyrones and 2-pyridones, allowing access to a previously unavailable class of C-5 cyclised products with an unstudied biological profile. A C–Cl bond was retained at C-3 during the direct arylation process allowing further derivatisation at C-3, using a Suzuki–Miyaura cross-coupling reaction.

KW - C-H activation

KW - Cross-coupling

KW - Heterocycles

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KW - Synthetic methods

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Access to Some C5-Cyclised 2-Pyrones and 2-Pyridones via Direct Arylation; Retention of Chloride as a Synthetic Handle

Abstract

Bibliographical note

Keywords

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