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

49 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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10.1021/ol006097b

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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",

number = "15",

}

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.

UR - https://www.scopus.com/pages/publications/0034720918

UR - https://www.scopus.com/pages/publications/0034720918#tab=citedBy

U2 - 10.1021/ol006097b

DO - 10.1021/ol006097b

M3 - Article

C2 - 10930278

AN - SCOPUS:0034720918

SN - 1523-7060

VL - 2

SP - 2339

EP - 2341

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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