Simple and facile electrocatalytic approach to medicinally relevant spirocyclopropylpyrazolones directly from pyrazoline-5-ones and activated olefins

Elinson, Michaïl N.; Dorofeeva, Evgeniya O.; Vereshchagin, A. N.; Korshunov, Alexander D.; Egorov, Mikhail P.

doi:10.1007/s11164-015-2142-y

Cited by 19 publications

(4 citation statements)

References 20 publications

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“…The structures of the major (2RS,3SR) 3m-3p isomers were established earlier on the data of NOESY. 40 It should be noted that sodium bromide in methanol is a more effective mediator than PyHBr in acetonitrile for the electrochemical synthesis of spirocyclopropanes 3i-3p. 29,40 Apparently this is due to the particularity of the reaction mechanism (Scheme 4).…”

Section: Methodsmentioning

confidence: 99%

Pyridinium bromide as a mediator in electrochemical reactions: the preparation of cyclopropane-1,1-dicarbonitriles

Vereshchagin¹,

Dorofeeva²,

Elinson³

et al. 2019

Arkivoc

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Pyridinium bromide has been tested as a new mediator for electrochemical transformations in methanol and acetonitrile. An efficient protocol for the synthesis of cyclopropanes via the electrochemical transformations of alkylidenemalononitriles and C-H acids (malononitrile, malonic ester, N,N-dimethylbarbituric acid, pyrazolin-5-ones) has been developed. The chemistry proceeds in a simple undivided cell under constant current conditions employing a substoichiometric amount of PyHBr that serves both as a redox catalyst and a supporting electrolyte; in this manner additional conducting salt is not required.

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Section: Methodsmentioning

confidence: 99%

Pyridinium bromide as a mediator in electrochemical reactions: the preparation of cyclopropane-1,1-dicarbonitriles

Vereshchagin¹,

Dorofeeva²,

Elinson³

et al. 2019

Arkivoc

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“…In 2016, the electrolysis of pyrazoline‐5‐ones and activated olefins using NaBr as mediator in MeOH in an undivided cell using alkali metal halides led to effective synthesis of the functionalized spirocyclopropyl pyrazolone derivatives 102 in 50–85 % yields (Scheme ) …”

Section: Electrogenerated Based Michael Addition Reactionmentioning

confidence: 99%

Electrochemically Induced Michael Addition Reaction: An Overview

Fotouhi

Heravi

Zadsirjan

et al. 2018

The Chemical Record

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Due to its high potential for the formation of carbon‐carbon bonds, Michael addition reaction is one of the closest reactions to the heart of synthetic organic chemists. Electrochemistry presents a very stimulating and divergent resource for selective oxidation and reduction in organic chemistry, generating activated species, for example radical anions or radical cations. In this review, we try to underscore usefulness of electrogenerated Michael addition reaction with the hope of encouraging synthetic organic chemists to contemplate it, as an efficient and green strategy when it is required in their designed multi‐step reaction pathways.

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“…[3] For example, the spirocyclopropanyl pyrazolone derivative IV exhibits antiinfective activity, [3f] and the spirocyclopropanyl pyrazolone derivative V was patented as advanced glycation end product (AGE) formation inhibitors intended for treatment of human schizophrenia [3g] . Given the excellent biological properties and the importance of the structural core, the synthesis of functionalized spiropyrazolone skeleton is of great importance in synthetic chemistry, and considerable efforts have been contributed to construct these spirocyclopropanyl pyrazolone cores both in organic synthesis and medicinal chemistry [3g,4] . Representative synthetic strategies toward these spiro skeletons include intramolecular cyclization, [4a,b,g] [2+1] annulation reaction, [4e,k] cascade reaction [4h,j,l–n] .…”

Section: Introductionmentioning

confidence: 99%

Sulfide‐Catalyzed Diastereoselective Spirocyclopropanation: Constructing Spiro‐cyclopropanyl‐pyrazolones From α‐Arylidenepyrazolones

Zhao

et al. 2021

Asian J Org Chem

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An efficient and diastereoselective [2 + 1] annulation of arylidenepyrazolones with bromides has been developed that relies on in situ formation of sulfur ylide via a direct sulfide-catalyzed process. A variety of spirocyclopropanyl pyrazolones were achieved in good to excellent yields (up to 93% yield) with high diastereoselectives (up to 20 : 1 dr). Meanwhile, several spirocyclopropanyl compounds were also prepared from corresponding enones. This catalytic strategy exhibits good functional group tolerance, gram-scale capacity and broad substrate scope, and provides various spirocyclopropanyl derivatives.

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Simple and facile electrocatalytic approach to medicinally relevant spirocyclopropylpyrazolones directly from pyrazoline-5-ones and activated olefins

Cited by 19 publications

References 20 publications

Pyridinium bromide as a mediator in electrochemical reactions: the preparation of cyclopropane-1,1-dicarbonitriles

Pyridinium bromide as a mediator in electrochemical reactions: the preparation of cyclopropane-1,1-dicarbonitriles

Electrochemically Induced Michael Addition Reaction: An Overview

Sulfide‐Catalyzed Diastereoselective Spirocyclopropanation: Constructing Spiro‐cyclopropanyl‐pyrazolones From α‐Arylidenepyrazolones

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