Simple and scalable electrochemical oxidation of the electron-rich benzene ring followed by intramolecular capture of reactive cation-radical intermediates opens access to spirocyclic morpholines and tetrahydrofurans. The obtained molecules can be readily modified to value-added building blocks.
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"Angular" Spirocyclic Azetidines: Synthesis, Characterization, and Evaluation in Drug Discovery.
Angew Chem Int Ed Engl
December 2024
Enamine Ltd, Winston Churchill st. 78, 02094, Kyiv, Ukraine.
The previously neglected "angular" spirocyclic azetidines have been synthesized, characterized, and validated in drug discovery. We have shown that these compounds could act as bioisosteres for common saturated six-membered heterocycles. Their incorporation into the structure of the anticancer drug Sonidegib (instead of morpholine), and Danofloxacine (instead of piperazine) provided novel patent-free analogs with similar physicochemical properties and high activity.
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View Article and Find Full Text PDFElectrochemical synthesis of spirocyclic morpholines and tetrahydrofurans an oxidative dearomatisation strategy.
Org Biomol Chem
September 2023
Department of Chemistry, School of Sciences and Humanities, Nazarbayev University, 53 Kabanbay Batyr Ave., 010000 Astana, Kazakhstan.
Simple and scalable electrochemical oxidation of the electron-rich benzene ring followed by intramolecular capture of reactive cation-radical intermediates opens access to spirocyclic morpholines and tetrahydrofurans. The obtained molecules can be readily modified to value-added building blocks.
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Int J Mol Sci
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JSC A. B. Bekturov Institute of Chemical Sciences, 106 Shokan Ualikhanov St., Almaty 050010, Kazakhstan.
Our research area is related to the spiropyrazolinium-containingcompounds, which are insufficiently studied compared with pyrazoline-containing compounds. Nitrogen-containing azoniaspiromolecules have also been well studied. In drug design and other areas, they are a priori important structures, since rigid spirocyclic scaffolds with the reduced conformational entropy are able to organize a closely spaced area.
View Article and Find Full Text PDFSpirocyclic Nitroxides as Versatile Tools in Modern Natural Sciences: From Synthesis to Applications. Part I. Old and New Synthetic Approaches to Spirocyclic Nitroxyl Radicals.
Molecules
January 2021
Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences (SB RAS), Academician Lavrentiev Ave. 9, Novosibirsk 630090, Russia.
Spirocyclic nitroxyl radicals (SNRs) are stable paramagnetics bearing spiro-junction at a-, b-, or g-carbon atom of the nitroxide fragment, which is part of the heterocyclic system. Despite the fact that the first representatives of SNRs were obtained about 50 years ago, the methodology of their synthesis and their usage in chemistry and biochemical applications have begun to develop rapidly only in the last two decades. Due to the presence of spiro-function in the SNRs molecules, the latter have increased stability to various reducing agents (including biogenic ones), while the structures of the biradicals (SNBRs) comprises a rigid spiro-fused core that fixes mutual position and orientation of nitroxide moieties that favors their use in dynamic nuclear polarization (DNP) experiments.
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