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

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

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DGS_ADS_Pyridines_Org_Lett_Final.pdf (515.4Kb)

Date

19/12/2014

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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.

Citation

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. 16 , no. 24 , pp. 6496-6499 . https://doi.org/10.1021/ol503360q

Publication

Organic Letters

Status

Peer reviewed

DOI

https://doi.org/10.1021/ol503360q

ISSN

1523-7060

Type

Journal article

Rights

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

Description

We thank the Royal Society (ADS), Syngenta/EPSRC (DGS), and the EPSRC National Mass Spectrometry Facility at Swansea University.

Collections

University of St Andrews Research

URI

http://hdl.handle.net/10023/7896