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

Research output: Contribution to journal › Article

4 Citations

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.

Language	English
Journal	Organic Letters
Early online date	16 Jun 2017
DOIs	10.1021/acs.orglett.7b01481
Publication status	E-pub ahead of print - 16 Jun 2017

Fingerprint

Cyclic Ethers

Chlorides

ethers

pyridines

chlorides

oxides

Labeling

isotopic labeling

carbenes

Electrons

Substrates

Experiments

pyridine N-oxide

electrons

Keywords

acyl chloride
pyridine N-oxides
cyclic ethers

Cite this

Jones, D. H., Kay, S. T., McLellan, J. A., Kennedy, A. R., & Tomkinson, N. C. O. (2017). A regioselective three component reaction of pyridine N-oxides, acyl chlorides and cyclic ethers. Organic Letters. https://doi.org/10.1021/acs.orglett.7b01481

Jones, D. Heulyn ; Kay, Steven T. ; McLellan, Jayde A. ; Kennedy, Alan R. ; Tomkinson, Nicholas C. O. / A regioselective three component reaction of pyridine N-oxides, acyl chlorides and cyclic ethers. In: Organic Letters. 2017.

@article{ff383e8955e744679462b849b08ec3ba,

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",

author = "Jones, {D. Heulyn} and Kay, {Steven T.} and McLellan, {Jayde A.} and Kennedy, {Alan R.} and Tomkinson, {Nicholas C. O.}",

year = "2017",

month = "6",

day = "16",

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

language = "English",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

}

Jones, DH, Kay, ST , McLellan, JA , Kennedy, AR & Tomkinson, NCO 2017, 'A regioselective three component reaction of pyridine N-oxides, acyl chlorides and cyclic ethers' Organic Letters. https://doi.org/10.1021/acs.orglett.7b01481

A regioselective three component reaction of pyridine N-oxides, acyl chlorides and cyclic ethers. / Jones, D. Heulyn; Kay, Steven T.; McLellan, Jayde A.; Kennedy, Alan R.; Tomkinson, Nicholas C. O.

In: Organic Letters, 16.06.2017.

Research output: Contribution to journal › Article

TY - JOUR

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

T2 - Organic Letters

JF - Organic Letters

SN - 1523-7060

ER -