Synthesis 2013; 45(23): 3288-3294
DOI: 10.1055/s-0033-1338548
paper
© Georg Thieme Verlag Stuttgart · New York

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: [email protected]
,
Sarah Berlin
Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany   Fax: +49(30)83855367   eMail: [email protected]
,
Hans-Ulrich Reissig*
Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany   Fax: +49(30)83855367   eMail: [email protected]
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Publikationsverlauf

Received: 07. August 2013

Accepted after revision: 16. September 2013

Publikationsdatum:
10. Oktober 2013 (online)


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.

Supporting Information

 
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