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B. Frontana-Uribe, R. Little, J. Ibanez, A. Palma, R. Vasquez-Medrano (2010)
Organic electrosynthesis: a promising green methodology in organic chemistryGreen Chemistry, 12
J. Poupaert, P. Carato, E. Colacino, S. Yous (2005)
2(3H)-benzoxazolone and bioisosters as "privileged scaffold" in the design of pharmacological probes.Current medicinal chemistry, 12 7
G. Nikishin, M. Elinson, I. Makhova (1988)
Electrocatalytic Haloform Reaction: Transformation of Methyl Ketones into Methyl EstersAngewandte Chemie, 27
M. Elinson, Sergey Feducovich, Z. Starikova, A. Vereshchagin, S. Gorbunov, G. Nikishin (2005)
Stereoselective electrocatalytic transformation of arylidene- or alkylidenemalononitriles and malonate into alkyl (1R,5R,6R)* 6-substituted 5-cyano-4,4-dialkoxy-2-oxo-3-azabicyclo[3.1.0]hexane-1-carboxylatesTetrahedron Letters, 46
S. Higson, Fabiana Subrizi, T. Sheppard, H. Hailes (2016)
Chemical cascades in water for the synthesis of functionalized aromatics from furfuralsGreen Chemistry, 18
M. Elinson, E. Dorofeeva, A. Vereshchagin, Ruslan Nasybullin, M. Egorov (2015)
Electrocatalytic stereoselective transformation of aldehydes and two molecules of pyrazolin-5-one into (R*,R*)-bis(spiro-2,4-dihydro-3H-pyrazol-3-one)cyclopropanesCatalysis Science & Technology, 5
D. Roman, J. Talbot, R. Roof, R. Sunahara, J. Traynor, R. Neubig (2007)
Identification of Small-Molecule Inhibitors of RGS4 Using a High-Throughput Flow Cytometry Protein Interaction AssayMolecular Pharmacology, 71
Christophe Laroche, J. Behr, J. Szymoniak*, P. Bertus, C. Schütz, P. Vogel, R. Plantier-Royon (2006)
Spirocyclopropyl pyrrolidines as a new series of α-l-fucosidase inhibitorsBioorganic & Medicinal Chemistry, 14
M. Elinson, E. Dorofeeva, A. Vereshchagin, G. Nikishin (1996)
Electrochemical synthesis of cyclopropanesRussian Chemical Reviews, 84
R. Francke, R. Little (2014)
Redox catalysis in organic electrosynthesis: basic principles and recent developments.Chemical Society reviews, 43 8
R. Desimone, K. Currie, S. Mitchell, J. Darrow, D. Pippin (2004)
Privileged structures: applications in drug discovery.Combinatorial chemistry & high throughput screening, 7 5
A. Gennaro, A. Isse, P. Mussini (2015)
Activation of the Carbon–Halogen Bond
D. Chen, Rebecca Pouwer, Jean-Alexandre Richard (2012)
Recent advances in the total synthesis of cyclopropane-containing natural products.Chemical Society reviews, 41 13
G. Nikishin, M. Elinson, S. Fedukovich (1986)
Electrochemical dehydrotrimerization of dimethyl malonate to the hexamethyl ester of cyclopropanehexacarboxylic acidBulletin of the Academy of Sciences of the USSR, Division of chemical science, 35
T. Fuchigami, S. Inagi, M. Atobe (2014)
Fundamentals and Applications of Organic Electrochemistry: Synthesis, Materials, Devices
V. Sandanayaka, Amar Prashad, Youjun Yang, R. Williamson, Yang-i Lin, T. Mansour (2003)
Spirocyclopropyl β-Lactams as Mechanism-Based Inhibitors of Serine β-Lactamases. Synthesis by Rhodium-Catalyzed Cyclopropanation of 6-Diazopenicillanate SulfoneJournal of Medicinal Chemistry, 46
Christoph Grondal, M. Jeanty, D. Enders (2010)
Organocatalytic cascade reactions as a new tool in total synthesis.Nature chemistry, 2 3
Peng‐Fei Xu, Wen Wang (2014)
Catalytic cascade reactions
A. Patchett, R. Nargund (2000)
Chapter 26. Privileged structures — An updateAnnual Reports in Medicinal Chemistry, 35
M. Elinson, T. Lizunova, M. Dekaprilevich, Y. Struchkov, G. Nikishin (1993)
Electrochemical Cyclotrimerization of Cyanoacetic Ester into trans-1,2,3-Tricyanocyclopropane-1,2,3-TricarboxylateMendeleev Communications, 3
(2006)
Methods and compositions for specific inhibition of protein splicing by small molecules
Zhenlei Zhang, Jihu Su, Zhenggen Zha, Zhiyong Wang (2013)
Electrochemical synthesis of the aryl α-ketoesters from acetophenones mediated by KI.Chemistry, 19 52
A. Vereshchagin, M. Elinson, T. Zaimovskaya, G. Nikishin (2008)
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 methanolTetrahedron, 64
(2006)
Methods and compositions for specific inhibition of protein splicing by small molecules . WO 2006079057 A 2 , 2006
K. Yamaguchi, Yuji Kazuta, K. Hirano, S. Yamada, A. Matsuda, S. Shuto (2008)
Synthesis of 1-arylpiperazyl-2-phenylcyclopropanes designed as antidopaminergic agents: cyclopropane-based conformationally restricted analogs of haloperidol.Bioorganic & medicinal chemistry, 16 19
Yuri Ogibin, M. Elinson, G. Nikishin (2009)
Mediator oxidation systems in organic electrosynthesisRussian Chemical Reviews, 78
M. Elinson, A. Dorofeev, Sergey Feducovich, P. Belyakov, G. Nikishin (2007)
Stereoselective Electrocatalytic Oxidative Coupling of Phenylacetonitriles: Facile and Convenient Way to trans‐α,β‐DicyanostilbenesEuropean Journal of Organic Chemistry, 2007
G. Nikishin, M. Elinson, T. Lizunova, B. Ugrak (1991)
Electrochemical transformation of malononitrile and ketones into 3,3-disubstituted-1,1,2,2-tetracyanocyclopropanesTetrahedron Letters, 32
P. Wender (2014)
Toward the ideal synthesis and molecular function through synthesis-informed design.Natural product reports, 31 4
M. Elinson, T. Lizunova, B. Ugrak, M. Dekaprilevich, G. Nikishin, Y. Struchkov (1993)
Electrochemical transformation of cyanoacetic ester and aldehydes into 3-substituted 1,2-dicyanocyclopropane-1,2-dicarboxylatesTetrahedron Letters, 34
M. Elinson, Sergey Feducovich, S. Bushuev, Alexander Zakharenkov, D. Pashchenko, G. Nikishin (1998)
Electrochemical transformation of malonate and alkylidenemalonates into 3-substituted cyclopropane-1,1,2,2-tetracarboxylatesMendeleev Communications, 8
M. Elinson, Sergey Feducovich, Z. Starikova, A. Vereshchagin, G. Nikishin (2004)
Stereoselective electrocatalytic transformation of arylidenemalononitriles and malononitrile into (1R,5S,6R)*-6-aryl-2-amino-4,4-dialkoxy-1,5-dicyano-3-azabicyclo[3.1.0]hex-2-enesTetrahedron, 60
The electrochemically induced reaction of heterocyclic ketones and two equivalents of malononitrile in an undivided cell in alcohols in the presence of sodium bromide as mediator leading to the selective formation of substituted 6-heterospirocyclopropane-1,1,2,2-tetracarbonitriles in 50–75% yields as a result of the complex cascade process has been investigated. This new electrocatalytic cascade process smoothly proceeds with different types of heterocyclic ketones and resulted in ‘one-pot’ formation of 6-heterospirocyclopropane-1,1,2,2-tetracarbonitriles with prominent pharmacological and physiological activity. The application of this electrochemical cascade method to the formation of medicinally relevant substituted 6-heterospiro[2.5]octane-1,1,2,2-tetracarbonitriles is also beneficial from the viewpoint of diversity-oriented large-scale processes. Graphical abstract Keywords Electrochemical process Cascade reaction Heterocyclic ketones Malononitrile 6-Heterospiro[2.5]octane- 1,1,2,2-tetracarbonitrile 6-Heterospirocyclopropane-1,1,2,2-tetracarbonitrile Introduction privileged scaffolds tend to contain rigid heterocyclic system with predefined spatial orientation of functional In the last decades, the ideas and principles of ‘‘privileged groups for target recognition [3]. medicinal structures’’ [1, 2] have evolved to one of the Cyclopropane ring is considered as the main structural basic approaches for drug discovery search. Generally, the feature for lots of synthetic and naturally occurring com- pounds with inherent spectrum of biological activity such as enzyme inhibition or antibiotic, antitumor, antiviral, and &
Monatshefte für Chemie - Chemical Monthly – Springer Journals
Published: Feb 15, 2018
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