A general preparation of pyridines and pyridones via the annulation of ketones and esters

J. F. Marcoux; F. A. Marcotte; J. Wu; P. G. Dormer; I. W. Davies; D. Hughes; P. J. Reider

doi:10.1021/jo0155198

A general preparation of pyridines and pyridones via the annulation of ketones and esters

J. F. Marcoux
, F. A. Marcotte
, J. Wu
, P. G. Dormer
, I. W. Davies
, D. Hughes
, P. J. Reider

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

59 Scopus citations

Abstract

A general preparation of pyridines 4a-f from stabilized ketones 3a-c and aryl ketones 3d-f is described. The annulation of stabilized esters 3g,h gives access to the corresponding 2-pyridones 4g,h. The annulation reactions proceed in fair to excellent yields (46-87%) with vinamidinium hexafluorophosphate salts 2a-d containing electron-withdrawing groups at the β-position. The mechanism of the reaction was investigated by NMR and proceeds through the formation of a dienaminone intermediate.

Original language	English (US)
Pages (from-to)	4194-4199
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	66
Issue number	12
DOIs	https://doi.org/10.1021/jo0155198
State	Published - Jun 15 2001
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo0155198

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@article{40637a45541f402aab5405b8a6337554,

title = "A general preparation of pyridines and pyridones via the annulation of ketones and esters",

abstract = "A general preparation of pyridines 4a-f from stabilized ketones 3a-c and aryl ketones 3d-f is described. The annulation of stabilized esters 3g,h gives access to the corresponding 2-pyridones 4g,h. The annulation reactions proceed in fair to excellent yields (46-87\%) with vinamidinium hexafluorophosphate salts 2a-d containing electron-withdrawing groups at the β-position. The mechanism of the reaction was investigated by NMR and proceeds through the formation of a dienaminone intermediate.",

author = "Marcoux, \{J. F.\} and Marcotte, \{F. A.\} and J. Wu and Dormer, \{P. G.\} and Davies, \{I. W.\} and D. Hughes and Reider, \{P. J.\}",

year = "2001",

month = jun,

day = "15",

doi = "10.1021/jo0155198",

language = "English (US)",

volume = "66",

pages = "4194--4199",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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TY - JOUR

T1 - A general preparation of pyridines and pyridones via the annulation of ketones and esters

AU - Marcoux, J. F.

AU - Marcotte, F. A.

AU - Wu, J.

AU - Dormer, P. G.

AU - Davies, I. W.

AU - Hughes, D.

AU - Reider, P. J.

PY - 2001/6/15

Y1 - 2001/6/15

N2 - A general preparation of pyridines 4a-f from stabilized ketones 3a-c and aryl ketones 3d-f is described. The annulation of stabilized esters 3g,h gives access to the corresponding 2-pyridones 4g,h. The annulation reactions proceed in fair to excellent yields (46-87%) with vinamidinium hexafluorophosphate salts 2a-d containing electron-withdrawing groups at the β-position. The mechanism of the reaction was investigated by NMR and proceeds through the formation of a dienaminone intermediate.

AB - A general preparation of pyridines 4a-f from stabilized ketones 3a-c and aryl ketones 3d-f is described. The annulation of stabilized esters 3g,h gives access to the corresponding 2-pyridones 4g,h. The annulation reactions proceed in fair to excellent yields (46-87%) with vinamidinium hexafluorophosphate salts 2a-d containing electron-withdrawing groups at the β-position. The mechanism of the reaction was investigated by NMR and proceeds through the formation of a dienaminone intermediate.

UR - https://www.scopus.com/pages/publications/0035874713

UR - https://www.scopus.com/pages/publications/0035874713#tab=citedBy

U2 - 10.1021/jo0155198

DO - 10.1021/jo0155198

M3 - Article

C2 - 11397153

AN - SCOPUS:0035874713

SN - 0022-3263

VL - 66

SP - 4194

EP - 4199

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 12

ER -

A general preparation of pyridines and pyridones via the annulation of ketones and esters

Abstract

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