Access to some C5-cyclised 2 pyrones and 2-pyridones via direct arylation; retention of chloride as a synthetic handle
McGlacken, Gerard P.; Fairlamb, Ian; Prendergast, Aisling; Pardo, Leticia
Date:
2017-08-04
Copyright:
© 2017, John Wiley & Sons Ltd. This is the peer reviewed version of the following article: McGlacken, G. P., Fairlamb, I., Prendergast, A. and Pardo, L. (2017) 'Access to some C5-cyclised 2 pyrones and 2-pyridones via direct arylation; retention of chloride as a synthetic handle', European Journal of Organic Chemistry, 2017(34), pp. 5119-5124, which has been published in final form at http://dx.doi.org/ 10.1002/ejoc.201700980. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
Full text restriction information:
Access to this article is restricted until 12 months after publication by request of the publisher.
Restriction lift date:
2018-08-04
Citation:
McGlacken, G. P., Fairlamb, I., Prendergast, A. and Pardo, L. (2017) 'Access to some C5-cyclised 2 pyrones and 2-pyridones via direct arylation; retention of chloride as a synthetic handle', European Journal of Organic Chemistry, 2017(34), pp. 5119-5124. doi:10.1002/ejoc.201700980
Abstract:
The synthetic effort towards the functionalisation of C-H bonds on 2 pyrones and 2-pyridones has been funnelled 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, which we have demonstrated with a proof-of-principle Suzuki-Miyaura cross-coupling reaction.
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