原创力文档conjugate addition of nucleophiles to the vinyl function of 2-chloro-4-vinylpyrimidine derivatives共轭乙烯基函数的亲核试剂的2-chloro-4-vinylpyrimidine衍生品.pdfVIP
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conjugate addition of nucleophiles to the vinyl function of 2-chloro-4-vinylpyrimidine derivatives共轭乙烯基函数的亲核试剂的2-chloro-4-vinylpyrimidine衍生品
Molecules 2010, 15, 1973-1984; doi:10.3390/molecule
OPEN ACCESS
molecules
ISSN 1420-3049
/journal/molecules
Article
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; E-Mail: lucjan@.
Received: 2 March 2010; in revised form: 9 March 2010 / Accepted: 18 March 2010 /
Published: 19 March 2010
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-vinyl-
quinazoline 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
1. Introduction
Few addition reactions across the vinyl group of vinyl-substituted heterocyclic compounds are
known. Photoirradiation of 2-vinylpyridine in aci
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