Affiliation:
1. Homolytic Reactions Research Laboratory, N. D. Zelinsky Institute of Organic Chemistry, Leninsky prospect 47, 119991 Moscow, Russia
Abstract
The new type of the chemical cascade reaction was found: formation of cyclopropanes from carbonyl compounds and CH acid by the only bromine direct action. The action of aqueous bromine on the carbonyl compounds and malononitrile in EtOH-H2O solutions in the presence of NaOAc results in the formation of 3-substituted 1,1,2,2-tetracyanocyclopropanes in 48–93% yields. The latter are well-known precursors for the different bicyclic heterosystems, among them those containing cyclopropane ring and those possessing different types of pharmacological activity.
Funder
Russian Foundation for Basic Research
Cited by
4 articles.
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1. Unprecedented thermal condensation of tetracyanocyclopropanes to triazaphenalenes: a facile route for the design of novel materials for electronic applications;Chemical Communications;2017
2. Synthesis and Analgesic Activity of 9-Aryl-12-Imino-10,11-Dioxatricyclo[5.3.2.01,6]Dodecane-7,8,8-Tricarbonitriles and 3-Aryl-1,1,2,2-Tetracyanocyclopropanes;Pharmaceutical Chemistry Journal;2016-12
3. Facile and efficient approach for the synthesis of spirocyclopropylbarbiturates and 3-substituted-1,1,2,2-tetracyanocyclopropanes using N-halosulfonamides;Molecular Diversity;2016-06-13
4. Cascade Assembling of Isatins and Barbituric Acids: Facile and Efficient Way to 2′′H-Dispiro[indole-3,5′-furo[2,3-d]pyrimidine-6′,5′′-pyrimidine]-2,2′,2′′,4′,4′′,6′′-(1H,1′H,1′′H,3′H,3′′H)-hexone Scaffold;Journal of Heterocyclic Chemistry;2013-06