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Molecules 2010, 15(3), 1973-1984; doi:10.3390/molecules15031973

Conjugate Addition of Nucleophiles to the Vinyl Function of 2-Chloro-4-vinylpyrimidine Derivatives

Department of Chemistry, Georgia State University, Atlanta, Georgia 30302-4098, USA
On leave of absence from Department of Chemical Technology of Drugs, Medical University of Gdańsk, Al. Gen. Hallera 107, 80–416 Gdańsk, Poland.
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Author to whom correspondence should be addressed.
Received: 2 March 2010 / Revised: 9 March 2010 / Accepted: 18 March 2010 / Published: 19 March 2010
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Abstract

Conjugate addition reaction of various nucleophiles across the vinyl group of 2-chloro-4-vinylpyrimidine, 2-chloro-4-(1-phenylvinyl)pyrimidine and 2-chloro-4-vinylquinazoline provides the corresponding 2-chloro-4-(2-substituted ethyl)pyrimidines and 2-chloro-4-(2-substituted ethyl)quinazolines. Treatment of these products, without isolation, with N-methylpiperazine results in nucleophilic displacement of chloride and yields the corresponding 2,4-disubstituted pyrimidines and quinazolines.
Keywords: conjugate addition; vinylpyrimidine; vinylquinazoline conjugate addition; vinylpyrimidine; vinylquinazoline
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Raux, E.; Klenc, J.; Blake, A.; Sączewski, J.; Strekowski, L. Conjugate Addition of Nucleophiles to the Vinyl Function of 2-Chloro-4-vinylpyrimidine Derivatives. Molecules 2010, 15, 1973-1984.

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