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

doi:10.1021/ol503360q

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

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	6496-6499
Journal	Organic Letters
Volume	16
Issue number	24
Early online date	8 Dec 2014
DOIs	https://doi.org/10.1021/ol503360q
Publication status	Published - 19 Dec 2014

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10.1021/ol503360q

DGS_ADS Pyridines Org Lett Final
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
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title = "Synthesis of di-, tri-, and tetrasubstituted pyridines from (phenylthio)carboxylic acids and 2-[aryl(tosylimino)methyl]acrylates",

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.",

author = "Stark, \{Daniel Graham\} and O{\textquoteright}Riordan, \{Timothy J. C.\} and Smith, \{Andrew David\}",

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

year = "2014",

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doi = "10.1021/ol503360q",

language = "English",

volume = "16",

pages = "6496--6499",

journal = "Organic Letters",

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T1 - Synthesis of di-, tri-, and tetrasubstituted pyridines from (phenylthio)carboxylic acids and 2-[aryl(tosylimino)methyl]acrylates

AU - Stark, Daniel Graham

AU - O’Riordan, Timothy J. C.

AU - Smith, Andrew David

N1 - We thank the Royal Society (ADS), Syngenta/EPSRC (DGS), and the EPSRC National Mass Spectrometry Facility at Swansea University.

PY - 2014/12/19

Y1 - 2014/12/19

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/84919643291

U2 - 10.1021/ol503360q

DO - 10.1021/ol503360q

M3 - Article

SN - 1523-7060

VL - 16

SP - 6496

EP - 6499

JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

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

Abstract

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