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

doi:10.3390/molecules15031973

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

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

Elizabeth Raux, Jeffrey Klenc, Ava Blake, Jarosław Sączewski and Lucjan Strekowski *

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.

* Author to whom correspondence should be addressed.

Received: 2 March 2010; in revised form: 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

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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.

AMA 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(3):1973-1984.

Chicago/Turabian Style

Raux, Elizabeth; Klenc, Jeffrey; Blake, Ava; Sączewski, Jarosław; Strekowski, Lucjan. 2010. "Conjugate Addition of Nucleophiles to the Vinyl Function of 2-Chloro-4-vinylpyrimidine Derivatives." Molecules 15, no. 3: 1973-1984.

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