Affiliation:
1. 1N. D. Zelinsky Institute of Organic Chemistry, Leninsky prospect 47, Moscow 119991, Russia
Abstract
AbstractA new stereoselective cascade reaction of benzylidenecyanoacetates and 1,3-dimethylbarbituric acid by the action of bromine in the presence of a base into substituted (barbituric acid)-5-spirocyclopropanes is described. The yields are in the range of 60%–75%. Nuclear magnetic resonance (NMR) studies indicate that this cascade transformation results in the stereoselective formation of spiro products with trans-configuration of aryl and alkoxycarbonyl substituents in the cyclopropane ring. The products are a perspective class of compounds with prominent pharmacological and physiological activity.
Reference84 articles.
1. Low risk of development of substance dependence for barbiturates and clobazam prescribed as antiepileptic drugs: results from a questionnaire study;CNS Neurosci. Ther.,2009
2. Electrochemical dehydrotrimerization of dimethyl malonate to the hexamethyl ester of cyclopropanehexacarboxylic acid;Russ. Chem. Bull.,1986
3. Electrochemical transformation of malononitrile and ketones into 3,3-disubstituted-1,1,2,2-tetracyanocyclopropanes;Tetrahedron Lett.,1991
4. Electrocatalytic cascade multicomponent assembling: stereoselective one-pot synthesis of the substituted 3-azabicyclo 3.1.0 hexane-1-carboxylate system from aldehyde, malononitrile, malonate and methanol;Tetrahedron,2008
5. The electrochemical synthesis of cyclopropanes;Russ. J. Electrochem.,1996
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