Synthesis of di-, tri-, and tetrasubstituted pyridines from (phenylthio)carboxylic acids and 2-[aryl(tosylimino)methyl]acrylates
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An isothiourea-catalyzed Michael addition–lactamization followed by the sulfide oxidation–elimination/N- to O-sulfonyl transfer sequence for the formation of 2,3,5- and 2,3-substituted pyridine 6-tosylates from (phenylthio)acetic acids and α,β-unsaturated ketimines is described. Incorporation of the valuable 2-sulfonate group allows derivatization to a range of di-, tri-, and tetrasubstituted pyridines.
Stark , D G , O’Riordan , T J C & Smith , A D 2014 , ' Synthesis of di-, tri-, and tetrasubstituted pyridines from (phenylthio)carboxylic acids and 2-[aryl(tosylimino)methyl]acrylates ' Organic Letters , vol In press . DOI: 10.1021/ol503360q
Copyright © 2014 American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/ol503360q
We thank the Royal Society (ADS), Syngenta/EPSRC (DGS), and the EPSRC National Mass Spectrometry Facility at Swansea University.
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