A regioselective three component reaction of pyridine N-oxides, acyl chlorides and cyclic ethers

D. Heulyn Jones; Steven T. Kay; Jayde A. McLellan; Alan R. Kennedy; Nicholas C. O. Tomkinson

doi:10.1021/acs.orglett.7b01481

A regioselective three component reaction of pyridine N-oxides, acyl chlorides and cyclic ethers

D. Heulyn Jones, Steven T. Kay, Jayde A. McLellan, Alan R. Kennedy, Nicholas C. O. Tomkinson

Pure And Applied Chemistry

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Abstract

A novel 3-component reaction of pyridine N-oxides, acyl chlorides and cyclic ethers is described. Treatment of an electron defi-cient pyridine N-oxide with an acyl chloride in the presence of a cyclic ether at 25–50 °C leads to a substituted pyridine as a single regioisomer in up to 58% isolated yield. Isotopic labelling experiments and substrate scope support the reaction proceeding through a carbene intermediate.

Original language	English
Journal	Organic Letters
Early online date	16 Jun 2017
DOIs	https://doi.org/10.1021/acs.orglett.7b01481
Publication status	E-pub ahead of print - 16 Jun 2017

Keywords

acyl chloride
pyridine N-oxides
cyclic ethers

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10.1021/acs.orglett.7b01481

Jones-etal-OL-2017-A-regioselective-three-component-reaction-of-pyridine-N-oxidesAccepted author manuscript, 632 KB

http://pubs.acs.org/doi/abs/10.1021/acs.orglett.7b01481

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title = "A regioselective three component reaction of pyridine N-oxides, acyl chlorides and cyclic ethers",

abstract = "A novel 3-component reaction of pyridine N-oxides, acyl chlorides and cyclic ethers is described. Treatment of an electron defi-cient pyridine N-oxide with an acyl chloride in the presence of a cyclic ether at 25–50 °C leads to a substituted pyridine as a single regioisomer in up to 58% isolated yield. Isotopic labelling experiments and substrate scope support the reaction proceeding through a carbene intermediate.",

keywords = "acyl chloride, pyridine N-oxides, cyclic ethers",

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doi = "10.1021/acs.orglett.7b01481",

language = "English",

journal = "Organic Letters",

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T1 - A regioselective three component reaction of pyridine N-oxides, acyl chlorides and cyclic ethers

AU - Jones, D. Heulyn

AU - Kay, Steven T.

AU - McLellan, Jayde A.

AU - Kennedy, Alan R.

AU - Tomkinson, Nicholas C. O.

PY - 2017/6/16

Y1 - 2017/6/16

N2 - A novel 3-component reaction of pyridine N-oxides, acyl chlorides and cyclic ethers is described. Treatment of an electron defi-cient pyridine N-oxide with an acyl chloride in the presence of a cyclic ether at 25–50 °C leads to a substituted pyridine as a single regioisomer in up to 58% isolated yield. Isotopic labelling experiments and substrate scope support the reaction proceeding through a carbene intermediate.

AB - A novel 3-component reaction of pyridine N-oxides, acyl chlorides and cyclic ethers is described. Treatment of an electron defi-cient pyridine N-oxide with an acyl chloride in the presence of a cyclic ether at 25–50 °C leads to a substituted pyridine as a single regioisomer in up to 58% isolated yield. Isotopic labelling experiments and substrate scope support the reaction proceeding through a carbene intermediate.

KW - acyl chloride

KW - pyridine N-oxides

KW - cyclic ethers

UR - http://pubs.acs.org/doi/abs/10.1021/acs.orglett.7b01481

U2 - 10.1021/acs.orglett.7b01481

DO - 10.1021/acs.orglett.7b01481

M3 - Article

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

ER -

A regioselective three component reaction of pyridine N-oxides, acyl chlorides and cyclic ethers

Abstract

Keywords

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