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
State	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. DOI: 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

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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. DOI: 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

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AU - Jones,D. Heulyn

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AU - Kennedy,Alan R.

AU - Tomkinson,Nicholas C. O.

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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

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KW - cyclic ethers

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

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