Furan Analog of the Alkaloid Dubiamine Based on 5-Hydroxymethylfurfurol

Chemistry of Natural Compounds -     

Synthesis of Novel Exocyclic Allenes with a Norbornene Fragment

Russian Journal of Organic Chemistry - N-Substituted amino acids with a norbornene fragment were synthesized by the direct fusion of amino acids with endic anhydride at 150°C. The synthesized...     

Synthesis of New Methanofullerenes with Phthalimide Fragment

Bromo- and chloromethyl ketones based on N-phthalyl-substituted amino acids have been synthesized via the Arndt–Eistert reaction. The products [2+1] cycloaddition to the fullerene scaffold has afforded the monoadducts of fullerene C60.     

Kinetic study of the reaction of nucleophilic cyclopropanation of C60 fullerene with halogenated maleopimarimide

The kinetics of nucleophilic fullerene cyclopropanation by halomethyl ketones with a diterpene fragment has been studied by the Bingel method, and the influence of the biologically active cyclopropanating agent on the process has been estimated. It has been revealed that favorable conditions for carrying out the reaction result in maximum monofunctionalized methanofullerenes formation with the maximum yield.     

Antioxidant Activity of Methano- and Cyclopentenofullerenes

Kinetics and Catalysis - The rate constant of the reaction of methano- and cyclopentenofullerenes (С60R) with a peroxyl radical (PhCH(OO?)CH3) was measured in a model system of the...     

Synthesis of New Cyclopentenofullerenes Containing a Norbornene Fragment

Russian Journal of Organic Chemistry - Endic acid imides were synthesized by direct fusion of endic anhydride with various amino acids. Further transformations of the resulting acids gave new...     

Cyclopentene-fused [C60]-fullerenes: synthesis and electrochemical properties

New cyclopentene-fused [C60]-fullerene derivatives containing terpene moieties have been synthesized by [3?+?2]-addition to fullerene C₆₀. All obtained products were fully characterized by ¹H- and ¹³C-NMR, IR, and MS. The electrochemical properties have been studied by cyclic voltammograms (CV), combined with absorption spectra, which are consistent with those obtained from density functional theory (DFT) calculations. It was found that all fulleropyrrolidines showed very similar absorption spectra, orbital energies, in which electron densities in both the LUMO and HOMO are mainly located on the fullerene cage, suggesting that C₆₀ act as the acceptor. All the compounds exhibited good thermal stability. All determined characteristics of fullerene conjugates were compared to [6,6]-phenyl-C61-butyric acid methyl ester ([60]PCBM), a popular fullerene-containing compound.

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Ionic liquid-catalyzed and microwave-assisted syntheses of pyrrolizine- and indolizinedione derivatives

3H-Pyrrolo[2,1-a]isoindole-2,5-diones and isoindolo[2,1-a]quinoline-5,11-diones were synthesized by intramolecular cyclization of N-[2-oxo-3-(triphenyl-??⁵-phosphanylidene)propyl]- and N-[2-(triphenyl-??⁵-phosphanylidene)acetyl]phthalimides, respectively, in the presence of ionic liquid ([bmim][BF₄], 10 mol %) as catalyst or under microwave irradiation.     

Thermal oligomerization of methyl 4-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)buta-2,3-dienoate

Dimeric compounds formed as a result of thermal oligomerization of methyl 4-(1,3-dioxo-2,3- dihydro-1H-isoindol-2-yl)buta-2,3-dienoate were identified.     

Sulfur ylides 13. Synthesis and intramolecular cyclization of keto-stabilized sulfur ylides

Keto-stabilized sulfur mono-and bisylides were obtained from N-phthalylglutamic acid and their intramolecular cyclization was studied. The intramolecular cyclization of the ylide obtained at the α-carboxy group gave a product of the pyrrolizidinedione structure; bisylide yielded a cycloheptene derivative as the result of intramolecular recombination of intermediate dicarbene. The ylide obtained at the γ-carboxy group underwent no cyclization, giving methylthio ketone and oxo benzoate. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2771–2776, December, 2005.