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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.
Pritchard, Gareth J.
Weaver, George W.
|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|
|Publisher Link: ||http://dx.doi.org/10.1002/ejoc.201601156|
|Appears in Collections:||Closed Access (Chemistry)|
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