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Your search keyword '"Jayde A. McLellan"' showing total 2 results
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2 results on '"Jayde A. McLellan"'

1. Regioselective Reaction of Heterocyclic N-Oxides, an Acyl Chloride, and Cyclic Thioethers

Author

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

Subjects
010405 organic chemistry, Organic Chemistry, Regioselectivity, food and beverages, 010402 general chemistry, 01 natural sciences, Medicinal chemistry, Chloride, 0104 chemical sciences, chemistry.chemical_compound, Acyl chloride, chemistry, Thioether, Yield (chemistry), Pyridine, medicine, Diisopropyl ether, QD, Triethylamine, medicine.drug
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 a 74% isolated yield. The transformation can also be accomplished with alternative nitrogen containing heterocycles, 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.

Published
2018

2. Regioselective Three-Component Reaction of Pyridine N-Oxides, Acyl Chlorides, and Cyclic Ethers

Author

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

Subjects
010405 organic chemistry, Organic Chemistry, Nucleophilic acyl substitution, Regioselectivity, 010402 general chemistry, 01 natural sciences, Biochemistry, Medicinal chemistry, 0104 chemical sciences, Acylation, chemistry.chemical_compound, chemistry, Acyl chloride, Yield (chemistry), Pyridine, Structural isomer, Organic chemistry, QD, Physical and Theoretical Chemistry, Carbene
Abstract

A novel three-component reaction of pyridine N-oxides, acyl chlorides, and cyclic ethers is described. Treatment of an electron-deficient 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-labeling experiments and substrate scope support the reaction proceeding through a carbene intermediate.

Published
2017

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