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Synthesis 2003(18): 2815-2826  
DOI: 10.1055/s-2003-42480
PAPER
© Georg Thieme Verlag Stuttgart · New York

Straightforward Novel One-Pot Enaminone and Pyrimidine Syntheses by Coupling-Addition-Cyclocondensation Sequences

Alexei S. Karpov, Thomas J. J. Müller*
Organisch-Chemisches Institut der Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg
Fax: +49(6221)544205; e-Mail: Thomas_J.J.Mueller@urz.uni-heidelberg.de ;
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Publication History

Received 20 August 2003
Publication Date:
17 November 2003 (online)

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Abstract

The coupling of acid chlorides 1 with terminal alkynes 2 using only one equivalent (!) of triethylamine under Sonogashira conditions followed by subsequent addition of primary or secondary amines 4 to the intermediate alkynones 3 represents a straightforward one-pot three component access to enaminones 5 under mild conditions and in excellent yields. Furthermore, 2,4-di- and 2,4,6-trisubstituted pyrimidines 7 can be synthesized in moderate to good yields according to a highly flexible coupling-addition-cyclocondensation sequence.

Key words

catalysis - cross-couplings - enamines - heterocycles - vinylations­

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