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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.