Regioselective reaction of heterocyclic N-oxides, an acyl chloride and cyclic thioethers

Przemysslaw Frei, D. Heulyn Jones, Steven T. Kay, Jayde A. McLellan, Blair F. Johnston, Alan R. Kennedy, Nicholas C. O. Tomkinson

Research output: Contribution to journal › Article

2 Citations (Scopus)

Abstract

Treatment of electron deficient pyridine N-oxides with 4-nitrobenzoyl chloride and a cyclic thioether in the presence of triethylamine leads to the corresponding 2-functionalized product in up to 74% iso-lated yield. The transformation can also be accomplished with alternative nitrogen containing hetero-cycles including quinolines, pyrimidines, and pyrazines. To expand the scope of the transformation diisopropyl ether can be used as the reaction medium to allow for the use of solid thioether substrates.
LanguageEnglish
Number of pages8
JournalJournal of Organic Chemistry
Early online date18 Jan 2018
DOIs
Publication statusE-pub ahead of print - 18 Jan 2018

Fingerprint

Cyclic N-Oxides
Sulfides
Chlorides
Quinolines
Pyrazines
Pyrimidines
Nitrogen
Electrons
Substrates

Keywords

  • N-oxides
  • heterocycles
  • nitrogen

Cite this

Frei, Przemysslaw ; Jones, D. Heulyn ; Kay, Steven T. ; McLellan, Jayde A. ; Johnston, Blair F. ; Kennedy, Alan R. ; Tomkinson, Nicholas C. O. / Regioselective reaction of heterocyclic N-oxides, an acyl chloride and cyclic thioethers. In: Journal of Organic Chemistry. 2018.
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abstract = "Treatment of electron deficient pyridine N-oxides with 4-nitrobenzoyl chloride and a cyclic thioether in the presence of triethylamine leads to the corresponding 2-functionalized product in up to 74{\%} iso-lated yield. The transformation can also be accomplished with alternative nitrogen containing hetero-cycles including quinolines, pyrimidines, and pyrazines. To expand the scope of the transformation diisopropyl ether can be used as the reaction medium to allow for the use of solid thioether substrates.",
keywords = "N-oxides, heterocycles, nitrogen",
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note = "This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright {\circledC} American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.7b02457.",
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Frei, P, Jones, DH, Kay, ST, McLellan, JA, Johnston, BF, Kennedy, AR & Tomkinson, NCO 2018, 'Regioselective reaction of heterocyclic N-oxides, an acyl chloride and cyclic thioethers' Journal of Organic Chemistry. https://doi.org/10.1021/acs.joc.7b02457

Regioselective reaction of heterocyclic N-oxides, an acyl chloride and cyclic thioethers. / Frei, Przemysslaw; Jones, D. Heulyn; Kay, Steven T.; McLellan, Jayde A.; Johnston, Blair F.; Kennedy, Alan R.; Tomkinson, Nicholas C. O.

In: Journal of Organic Chemistry, 18.01.2018.

Research output: Contribution to journal › Article

TY - JOUR

T1 - Regioselective reaction of heterocyclic N-oxides, an acyl chloride and cyclic thioethers

AU - Frei, Przemysslaw

AU - Jones, D. Heulyn

AU - Kay, Steven T.

AU - McLellan, Jayde A.

AU - Johnston, Blair F.

AU - Kennedy, Alan R.

AU - Tomkinson, Nicholas C. O.

N1 - This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.7b02457.

PY - 2018/1/18

Y1 - 2018/1/18

N2 - Treatment of electron deficient pyridine N-oxides with 4-nitrobenzoyl chloride and a cyclic thioether in the presence of triethylamine leads to the corresponding 2-functionalized product in up to 74% iso-lated yield. The transformation can also be accomplished with alternative nitrogen containing hetero-cycles including quinolines, pyrimidines, and pyrazines. To expand the scope of the transformation diisopropyl ether can be used as the reaction medium to allow for the use of solid thioether substrates.

AB - Treatment of electron deficient pyridine N-oxides with 4-nitrobenzoyl chloride and a cyclic thioether in the presence of triethylamine leads to the corresponding 2-functionalized product in up to 74% iso-lated yield. The transformation can also be accomplished with alternative nitrogen containing hetero-cycles including quinolines, pyrimidines, and pyrazines. To expand the scope of the transformation diisopropyl ether can be used as the reaction medium to allow for the use of solid thioether substrates.

KW - N-oxides

KW - heterocycles

KW - nitrogen

UR - http://pubs.acs.org/journal/joceah

U2 - 10.1021/acs.joc.7b02457

DO - 10.1021/acs.joc.7b02457

M3 - Article

JO - Journal of Organic Chemistry

T2 - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

ER -

Frei P, Jones DH, Kay ST, McLellan JA, Johnston BF, Kennedy AR et al. Regioselective reaction of heterocyclic N-oxides, an acyl chloride and cyclic thioethers. Journal of Organic Chemistry. 2018 Jan 18. https://doi.org/10.1021/acs.joc.7b02457

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