Regio- and Stereoselective Alkylation of Pyridine-N-oxides: Synthesis of Substituted Piperidines and Pyridines

Deepak Kumar Barange; Magnus T. Johnson; Andrew G. Cairns; Roger Olsson; Fredrik Almqvist

doi:10.1021/acs.orglett.6b02667

Regio- and Stereoselective Alkylation of Pyridine-N-oxides: Synthesis of Substituted Piperidines and Pyridines

Deepak Kumar Barange, Magnus T. Johnson, Andrew G. Cairns, Roger Olsson (Lead / Corresponding author), Fredrik Almqvist (Lead / Corresponding author)

Drug Discovery Unit

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

Abstract

Regio- and stereoselective addition of alkyl Grignard reagents to pyridine-N-oxides gave C2-alkylated N-hydroxy-1,2,5,6-tetrahydropyridines and trans-2,3-disubstituted N-hydroxy-1,2,5,6-tetrahydropyridines in good to excellent yields. These intermediates were aromatized or alternatively reduced in one-pot methodologies for efficient syntheses of alkylpyridines or piperidines, respectively. These reactions have a broad substrate scope and short reaction times.

Original language	English
Pages (from-to)	6228-6231
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	24
Early online date	28 Nov 2016
DOIs	https://doi.org/10.1021/acs.orglett.6b02667
Publication status	Published - 16 Dec 2016

Keywords

Reagents
Stereoselectivity
Electrophiles
Alkyls
Piperidines

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.6b02667

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title = "Regio- and Stereoselective Alkylation of Pyridine-N-oxides: Synthesis of Substituted Piperidines and Pyridines",

abstract = "Regio- and stereoselective addition of alkyl Grignard reagents to pyridine-N-oxides gave C2-alkylated N-hydroxy-1,2,5,6-tetrahydropyridines and trans-2,3-disubstituted N-hydroxy-1,2,5,6-tetrahydropyridines in good to excellent yields. These intermediates were aromatized or alternatively reduced in one-pot methodologies for efficient syntheses of alkylpyridines or piperidines, respectively. These reactions have a broad substrate scope and short reaction times.",

keywords = "Reagents, Stereoselectivity, Electrophiles, Alkyls, Piperidines",

author = "Barange, {Deepak Kumar} and Johnson, {Magnus T.} and Cairns, {Andrew G.} and Roger Olsson and Fredrik Almqvist",

year = "2016",

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doi = "10.1021/acs.orglett.6b02667",

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volume = "18",

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journal = "Organic Letters",

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T1 - Regio- and Stereoselective Alkylation of Pyridine-N-oxides

T2 - Synthesis of Substituted Piperidines and Pyridines

AU - Barange, Deepak Kumar

AU - Johnson, Magnus T.

AU - Cairns, Andrew G.

AU - Olsson, Roger

AU - Almqvist, Fredrik

PY - 2016/12/16

Y1 - 2016/12/16

N2 - Regio- and stereoselective addition of alkyl Grignard reagents to pyridine-N-oxides gave C2-alkylated N-hydroxy-1,2,5,6-tetrahydropyridines and trans-2,3-disubstituted N-hydroxy-1,2,5,6-tetrahydropyridines in good to excellent yields. These intermediates were aromatized or alternatively reduced in one-pot methodologies for efficient syntheses of alkylpyridines or piperidines, respectively. These reactions have a broad substrate scope and short reaction times.

AB - Regio- and stereoselective addition of alkyl Grignard reagents to pyridine-N-oxides gave C2-alkylated N-hydroxy-1,2,5,6-tetrahydropyridines and trans-2,3-disubstituted N-hydroxy-1,2,5,6-tetrahydropyridines in good to excellent yields. These intermediates were aromatized or alternatively reduced in one-pot methodologies for efficient syntheses of alkylpyridines or piperidines, respectively. These reactions have a broad substrate scope and short reaction times.

KW - Reagents

KW - Stereoselectivity

KW - Electrophiles

KW - Alkyls

KW - Piperidines

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U2 - 10.1021/acs.orglett.6b02667

DO - 10.1021/acs.orglett.6b02667

M3 - Article

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SN - 1523-7060

VL - 18

SP - 6228

EP - 6231

JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

Regio- and Stereoselective Alkylation of Pyridine-N-oxides: Synthesis of Substituted Piperidines and Pyridines

Abstract

Keywords

ASJC Scopus subject areas

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