Methodology for regioselective synthesis of substituted pyridines via intramolecular oximino malonate hetero Diels-Alder reactions

Douglas C. Bland; Brian C. Raudenbush; Steven M. Weinreb

doi:10.1021/ol006575i

Methodology for regioselective synthesis of substituted pyridines via intramolecular oximino malonate hetero Diels-Alder reactions

Douglas C. Bland, Brian C. Raudenbush, Steven M. Weinreb

Chemistry

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

28 Scopus citations

Abstract

(Matrix Presented) Various substituted pyridines can be prepared regioselectively by a sequence involving an intramolecular thermal or high-pressure Diels-Alder cycloaddition of an oximino malonate dienophile tethered to a dienic carboxylic acid, followed by mild aromatization of the resulting cycloadduct with cesium carbonate in DMF at room temperature.

Original language	English (US)
Pages (from-to)	4007-4008
Number of pages	2
Journal	Organic Letters
Volume	2
Issue number	25
DOIs	https://doi.org/10.1021/ol006575i
State	Published - Dec 14 2000

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol006575i

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abstract = "(Matrix Presented) Various substituted pyridines can be prepared regioselectively by a sequence involving an intramolecular thermal or high-pressure Diels-Alder cycloaddition of an oximino malonate dienophile tethered to a dienic carboxylic acid, followed by mild aromatization of the resulting cycloadduct with cesium carbonate in DMF at room temperature.",

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AU - Bland, Douglas C.

AU - Raudenbush, Brian C.

AU - Weinreb, Steven M.

PY - 2000/12/14

Y1 - 2000/12/14

N2 - (Matrix Presented) Various substituted pyridines can be prepared regioselectively by a sequence involving an intramolecular thermal or high-pressure Diels-Alder cycloaddition of an oximino malonate dienophile tethered to a dienic carboxylic acid, followed by mild aromatization of the resulting cycloadduct with cesium carbonate in DMF at room temperature.

AB - (Matrix Presented) Various substituted pyridines can be prepared regioselectively by a sequence involving an intramolecular thermal or high-pressure Diels-Alder cycloaddition of an oximino malonate dienophile tethered to a dienic carboxylic acid, followed by mild aromatization of the resulting cycloadduct with cesium carbonate in DMF at room temperature.

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U2 - 10.1021/ol006575i

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Methodology for regioselective synthesis of substituted pyridines via intramolecular oximino malonate hetero Diels-Alder reactions

Abstract

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