Synthesis of di-, tri-, and tetrasubstituted pyridines from (phenylthio)carboxylic acids and 2-[aryl(tosylimino)methyl]acrylates

Daniel Graham Stark, Timothy J. C. O’Riordan, Andrew David Smith

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34 Citations (Scopus)
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Abstract

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.
Original languageEnglish
Pages (from-to)6496-6499
JournalOrganic Letters
Volume16
Issue number24
Early online date8 Dec 2014
DOIs
Publication statusPublished - 19 Dec 2014

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