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

Show simple item record

Files in this item

Name:: DGS_ADS_Pyridines_Org_Lett_Final.pdf
Size:: 515.4Kb
Format:: PDF

View/Open

Item metadata

dc.contributor.author	Stark, Daniel Graham
dc.contributor.author	O’Riordan, Timothy J. C.
dc.contributor.author	Smith, Andrew David
dc.date.accessioned	2015-12-08T00:11:21Z
dc.date.available	2015-12-08T00:11:21Z
dc.date.issued	2014-12-19
dc.identifier.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	en
dc.identifier.issn	1523-7060
dc.identifier.other	PURE: 159433772
dc.identifier.other	PURE UUID: c91e152e-4141-4e04-ba20-1a92bc53a168
dc.identifier.other	Scopus: 84919643291
dc.identifier.other	ORCID: /0000-0002-2104-7313/work/36567505
dc.identifier.other	WOS: 000346759900059
dc.identifier.uri	https://hdl.handle.net/10023/7896
dc.description	We thank the Royal Society (ADS), Syngenta/EPSRC (DGS), and the EPSRC National Mass Spectrometry Facility at Swansea University.	en
dc.description.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.
dc.language.iso	eng
dc.relation.ispartof	Organic Letters	en
dc.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	en
dc.subject	QD Chemistry	en
dc.subject.lcc	QD	en
dc.title	Synthesis of di-, tri-, and tetrasubstituted pyridines from (phenylthio)carboxylic acids and 2-[aryl(tosylimino)methyl]acrylates	en
dc.type	Journal article	en
dc.description.version	Postprint	en
dc.contributor.institution	University of St Andrews. School of Chemistry	en
dc.contributor.institution	University of St Andrews. Biomedical Sciences Research Complex	en
dc.contributor.institution	University of St Andrews. EaSTCHEM	en
dc.identifier.doi	https://doi.org/10.1021/ol503360q
dc.description.status	Peer reviewed	en
dc.date.embargoedUntil	2015-12-08

This item appears in the following Collection(s)

University of St Andrews Research

Show simple item record