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

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

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

Author(s) -

Prendergast Aisling M.,

Pardo Leticia M.,

Fairlamb Ian J. S.,

McGlacken Gerard P.

Publication year - 2017

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201700980

Subject(s) - chemistry , intramolecular force , reactivity (psychology) , combinatorial chemistry , chloride , coupling reaction , stereochemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology

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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