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A convergent, umpoled synthesis of 2-(1-amidoalkyl)pyridines

Tarn C. Johnson and Stephen P. Marsden

Beilstein J. Org. Chem. 2016, 12, 1–4. https://doi.org/10.3762/bjoc.12.1

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A convergent, umpoled synthesis of 2-(1-amidoalkyl)pyridines

Tarn C. Johnson and Stephen P. Marsden

Beilstein J. Org. Chem. 2016, 12, 1–4. https://doi.org/10.3762/bjoc.12.1

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Johnson, T. C.; Marsden, S. P. Beilstein J. Org. Chem. 2016, 12, 1–4. doi:10.3762/bjoc.12.1

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TY  - JOUR
A1  - Johnson, Tarn C.
A1  - Marsden, Stephen P.
T1  - A convergent, umpoled synthesis of 2-(1-amidoalkyl)pyridines
JF  - Beilstein Journal of Organic Chemistry
PY  - 2016///
VL  - 12
SP  - 1
EP  - 4
SN  - 1860-5397
DO  - 10.3762/bjoc.12.1
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.12.1
KW  - azlactones
KW  - pyridines
KW  - pyridine N-oxides
KW  - substitution
N2  - A convenient, one-pot, two-component synthesis of 2-(1-amidoalkyl)pyridines is reported, based upon the substitution of suitably-activated pyridine N-oxides by azlactone nucleophiles, followed by decarboxylative azlactone ring-opening. The synthesis obviates the need for precious metal catalysts to achieve a formal enolate arylation reaction, and constitutes a formally ‘umpoled’ approach to this valuable class of bioactive structures.
ER  -

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Scholarly Works

Tsunokawa, R.; Karuo, Y.; Tarui, A.; Sato, K.; Hosoya, T.; Agou, T.; Kawai, K.; Omote, M. Metal‐Free Arylation of Pyridine/Quinoline N‐Oxides with Indoles. European Journal of Organic Chemistry 2023, 26. doi:10.1002/ejoc.202300885
Johnson, T. C.; Marsden, S. P. Three-Component Synthesis of Pyridylacetic Acid Derivatives by Arylation/Decarboxylative Substitution of Meldrum's Acids. The Journal of organic chemistry 2022, 87, 13891–13894. doi:10.1021/acs.joc.2c01597
Liman, M.; Türkmen, Y. E. Development of one-pot benzylic amination reactions of azine N-oxides. Tetrahedron Letters 2018, 59, 1723–1727. doi:10.1016/j.tetlet.2018.03.062
Johnson, T. C.; Marsden, S. P. Precious-Metal-Free Heteroarylation of Azlactones: Direct Synthesis of α-Pyridyl, α-Substituted Amino Acid Derivatives. Organic letters 2016, 18, 5364–5367. doi:10.1021/acs.orglett.6b02731
Johnson, T. C.; Marsden, S. P. A Convergent, Umpoled Synthesis of 2‐(1‐Amidoalkyl)pyridines. ChemInform 2016, 47. doi:10.1002/chin.201615150

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