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Title: Pyridone functionalization: regioselective deprotonation of 6-methylpyridin-2(1H)- and -4(1H)-one derivatives
Authors: Fernandez D.-R., Beatriz
Elsegood, Mark R.J.
Fairley, Gary
Pritchard, Gareth J.
Weaver, George W.
Keywords: Heterocycles
Issue Date: 2016
Publisher: © Wiley-VCH Verlag
Citation: FERNANDEZ D.-R., B. ... et al, 2016. Pyridone functionalization: regioselective deprotonation of 6-methylpyridin-2(1H)- and -4(1H)-one derivatives. European Journal of Organic Chemistry, doi: 10.1002/ejoc.201601156.
Abstract: Selective functionalization at the α-methyl group of 1-substituted pyridin-2(1H)- and 4(1H)-ones (2- and 4-pyridones) can be achieved by appropriate choice of base. n-Butyllithium was found to effect clean 6(2)-methyl deprotonation of 1-benzyl-2- and -4-pyridone derivatives, while potassium hexamethyldisilazide (KHMDS) was the preferred reagent for methyl deprotonation of the corresponding 1-methyl-2- and -4-pyridones. Deprotonation proceeds smoothly at –78 °C, and the resulting anions react readily with a wide range of electrophiles (aldehydes, ketones, alkylating reagents, and an azo compound) under precise temperature control to form usefully functionalized 2- and 4-pyridones and quinolizinones.
Description: This paper is embargoed until twelve months after publication.
Sponsor: We thank AstraZeneca and Loughborough University for financial support, and the Engineering and Physical Sciences Research Council (EPSRC) UK National Mass Spectrometry Facility at Swansea for mass spectra.
Version: Accepted for publication
DOI: 10.1002/ejoc.201601156
URI: https://dspace.lboro.ac.uk/2134/22799
Publisher Link: http://dx.doi.org/10.1002/ejoc.201601156
ISSN: 1434-193X
Appears in Collections:Closed Access (Chemistry)

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