Electrocatalytic multicomponent cyclization of an aldehyde, malononitrile and a malonate into 3-substituted-2,2-dicyanocyclopropane-1,1-dicarboxylate—the first one-pot synthesis of a cyclopropane ring from three different molecules

Electrocatalytic and chemical methods in MHIRC reactions: the first example of the multicomponent assembly of medicinally relevant spirocyclopropylbarbiturates from three different molecules

“…16 The first synthesis of the cyclopropane structure from three different molecules was also achieved by us as a multicomponent cascade process in an electrocatalytic manner. 17 One of our last results in this area was the cascade chemical transformation of alkylidenemalononitriles and malononitrile into tetracyanosubstituted cyclopropanes realized under the action of active halogen containing compounds in ethanol in the presence of bases (Scheme 1). 18 In this type of the reaction halogenation of the CH-acid was followed by a Michael addition step, and is turned MHIRC -Michael Halogenation Initiated Ring Closure reaction by analogy with MIRC -Michael Initiated Ring Closure reaction 19 (Scheme 1).…”

One‐pot synthesis of new spiro[cyclopropane‐1,3′‐[3H]indol]‐2′(1′H)‐ones from 3‐phenacylideneoxindoles

“…Among the synthetic procedures for preparation of cyclopropane rings, the Michael initiated ring closure reaction [6,14,21,23,24] of a,b-unsaturated carbonyl compounds such as a,b-enones with dimethylsulfoxonium methylides or Corey-Chaykovsky reaction [27,28] is the well-known method. In this reaction, the cyclopropane ring forms between carbon atoms of positions 2 and 3 of enones by addition of a new methylene group (Scheme 1).…”

Electrocatalytic multicomponent cyclization of aromatic aldehydes, malononitrile, and malonates into 3-substituted 2,2-dicyanocyclopropane-1,1-dicarboxylates

“…Now we wish to report our results of multicomponent electrocatalytic «one pot» transformation of aldehydes 1a-p, malononitrile and malonic ester into 3 substituted 2,2 dicyanocyclopropane 1,1 dicarboxylates 2a-p in methanol in an undivided cell in the presence of double mediator system sodium bromide-sodium acetate (for preliminary communication see Ref. 37).…”