Trimethylsilyl Trifluoromethanesulfonate-Promoted Cyclocondensation of 
β-Ketoenamides and Subsequent Nonaflation to Pyrid-2-yl and Pyrid-4-yl Nonaflates as Flexible Precursors for Polysubstituted Pyridines

Paul Hommes; Sarah Berlin; Hans-Ulrich Reissig

doi:10.1055/s-0033-1338548

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(23): 3288-3294
DOI: 10.1055/s-0033-1338548

paper

Trimethylsilyl Trifluoromethanesulfonate-Promoted Cyclocondensation of β-Ketoenamides and Subsequent Nonaflation to Pyrid-2-yl and Pyrid-4-yl Nonaflates as Flexible Precursors for Polysubstituted Pyridines

Paul Hommes

Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany Fax: +49(30)83855367 eMail: hans.reissig@chemie.fu-berlin.de

,

Sarah Berlin

Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany Fax: +49(30)83855367 eMail: hans.reissig@chemie.fu-berlin.de

,

Hans-Ulrich Reissig*

Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany Fax: +49(30)83855367 eMail: hans.reissig@chemie.fu-berlin.de

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Abstract

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Dedicated to Professor Ernst Schaumann on the occasion of his 70th birthday

Abstract

The intramolecular condensation of β-ketoenamides to 2- and/or 4-pyridone derivatives using either KOt-Bu or trimethylsilyl trifluoromethanesulfonate/Hünig’s base was investigated. Subsequent nonaflation of the cyclization products allowed a facile purification and further functionalization through Suzuki–Miyaura couplings leading to new highly substituted pyridine derivatives. The dependence of the regioselectivity of cyclocondensation on the structure of the β-ketoenamides is discussed.

Key words

enamides - pyridines - cyclocondensation - nonaflates - cross couplings

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Referenzen

References

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