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

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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.
LanguageEnglish
JournalOrganic Letters
Early online date16 Jun 2017
DOIs
StateE-pub ahead of print - 16 Jun 2017

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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

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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",
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",

}

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 -