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.
Highlights
Few addition reactions across the vinyl group of vinyl-substituted heterocyclic compounds are known
Ethyl methyl sulfones are produced upon treatment of vinyl-substituted pyridines, pyrimidines and other diazines with sodium methanesulfinate under acidic conditions [3]
This report pertains to the conjugate addition reaction of N, O, S, and C-centered nucleophiles across the vinyl function of 2-chloro-4-vinylpyrimidine (2), 2-chloro-4-(1-phenylvinyl)pyrimidine (3), and 2-chloro-4-vinylquinazoline (19)
Summary
Few addition reactions across the vinyl group of vinyl-substituted heterocyclic compounds are known. This report pertains to the conjugate addition reaction of N-, O-, S-, and C-centered nucleophiles across the vinyl function of 2-chloro-4-vinylpyrimidine (2), 2-chloro-4-(1-phenylvinyl)pyrimidine (3), and 2-chloro-4-vinylquinazoline (19) These vinyl-bearing substrates are readily available by the addition reaction of a vinyllithium reagent to the formal C4=N3 bond of 2-chloropyrimidine and 2chloroquinazoline, followed by aromatization of the resultant adduct [4,5,6,7]. Another approach to similar compounds involves dehydration of an alcohol to the vinyl group [7]. Similar compounds have been shown to interact selectively with various serotonin receptors of the central nervous system (CNS) and have shown promise for the development as practical CNS drugs [6,8,9,10]
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