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

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

Research output: Contribution to journalArticle

26 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)4007-4008
Number of pages2
JournalOrganic Letters
Volume2
Issue number25
StatePublished - Dec 14 2000

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Pyridines
Aromatization
Diels-Alder reactions
Cycloaddition
Cycloaddition Reaction
cycloaddition
Carboxylic Acids
cesium
carboxylic acids
carbonates
pyridines
Hot Temperature
methodology
Pressure
Temperature
room temperature
synthesis
matrices
cesium carbonate
malonic acid

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Bland, Douglas C. ; Raudenbush, Brian C. ; Weinreb, Steven M. / Methodology for regioselective synthesis of substituted pyridines via intramolecular oximino malonate hetero Diels-Alder reactions. In: Organic Letters. 2000 ; Vol. 2, No. 25. pp. 4007-4008.
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Methodology for regioselective synthesis of substituted pyridines via intramolecular oximino malonate hetero Diels-Alder reactions. / Bland, Douglas C.; Raudenbush, Brian C.; Weinreb, Steven M.

In: Organic Letters, Vol. 2, No. 25, 14.12.2000, p. 4007-4008.

Research output: Contribution to journalArticle

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