Annulation of ketones with vinamidinium hexafluorophosphate salts: An efficient preparation of trisubstituted pyridines

Jean François Marcoux; Edward G. Corley; Kai Rossen; Phil Pye; Jimmy Wu; Michael A. Robbins; Ian W. Davies; Robert D. Larsen; Paul J. Reider

doi:10.1021/ol006097b

Annulation of ketones with vinamidinium hexafluorophosphate salts: An efficient preparation of trisubstituted pyridines

Jean François Marcoux, Edward G. Corley, Kai Rossen, Phil Pye, Jimmy Wu, Michael A. Robbins, Ian W. Davies, Robert D. Larsen, Paul J. Reider

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

47 Scopus citations

Abstract

(equation presented) α-Aryl ketones react with vinamidinium hexafluorophosphate salts to give access to the corresponding 3-arylpyridines. The annulation reactions proceed in good to excellent yields with vinamidinium salts containing electron-withdrawmg groups at the β-position (R₂). The reaction was applied to the preparation of the COX-2 specific inhibitor 5-chloro-3-(4-methylsulfonyl)phenyl-2-(2-methyl-5-pyridinyl)pyridine (1), as well as a series of analogues.

Original language	English (US)
Pages (from-to)	2339-2341
Number of pages	3
Journal	Organic letters
Volume	2
Issue number	15
DOIs	https://doi.org/10.1021/ol006097b
State	Published - Jul 27 2000
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Annulation of ketones with vinamidinium hexafluorophosphate salts: An efficient preparation of trisubstituted pyridines",

abstract = "(equation presented) α-Aryl ketones react with vinamidinium hexafluorophosphate salts to give access to the corresponding 3-arylpyridines. The annulation reactions proceed in good to excellent yields with vinamidinium salts containing electron-withdrawmg groups at the β-position (R2). The reaction was applied to the preparation of the COX-2 specific inhibitor 5-chloro-3-(4-methylsulfonyl)phenyl-2-(2-methyl-5-pyridinyl)pyridine (1), as well as a series of analogues.",

author = "Marcoux, {Jean Fran{\c c}ois} and Corley, {Edward G.} and Kai Rossen and Phil Pye and Jimmy Wu and Robbins, {Michael A.} and Davies, {Ian W.} and Larsen, {Robert D.} and Reider, {Paul J.}",

year = "2000",

month = jul,

day = "27",

doi = "10.1021/ol006097b",

language = "English (US)",

volume = "2",

pages = "2339--2341",

journal = "Organic letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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}

TY - JOUR

T1 - Annulation of ketones with vinamidinium hexafluorophosphate salts

T2 - An efficient preparation of trisubstituted pyridines

AU - Marcoux, Jean François

AU - Corley, Edward G.

AU - Rossen, Kai

AU - Pye, Phil

AU - Wu, Jimmy

AU - Robbins, Michael A.

AU - Davies, Ian W.

AU - Larsen, Robert D.

AU - Reider, Paul J.

PY - 2000/7/27

Y1 - 2000/7/27

N2 - (equation presented) α-Aryl ketones react with vinamidinium hexafluorophosphate salts to give access to the corresponding 3-arylpyridines. The annulation reactions proceed in good to excellent yields with vinamidinium salts containing electron-withdrawmg groups at the β-position (R2). The reaction was applied to the preparation of the COX-2 specific inhibitor 5-chloro-3-(4-methylsulfonyl)phenyl-2-(2-methyl-5-pyridinyl)pyridine (1), as well as a series of analogues.

AB - (equation presented) α-Aryl ketones react with vinamidinium hexafluorophosphate salts to give access to the corresponding 3-arylpyridines. The annulation reactions proceed in good to excellent yields with vinamidinium salts containing electron-withdrawmg groups at the β-position (R2). The reaction was applied to the preparation of the COX-2 specific inhibitor 5-chloro-3-(4-methylsulfonyl)phenyl-2-(2-methyl-5-pyridinyl)pyridine (1), as well as a series of analogues.

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DO - 10.1021/ol006097b

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JO - Organic letters

JF - Organic letters

IS - 15

ER -

Annulation of ketones with vinamidinium hexafluorophosphate salts: An efficient preparation of trisubstituted pyridines

Abstract

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