- Stereoselective hetero-Diels-Alder reaction of 3-nitro-2-trihalomethyl-2H-chromenes with 2,3-dihydrofuran and ethyl vinyl ether under solvent-free conditions
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3-Nitro-2-trifluoro(trichloro)methyl-2H-chromenes undergo heterodiene cycloaddition to 2,3-dihydrofuran and ethyl vinyl ether under solvent-free conditions producing novel cyclic nitronates with high stereoselectivity and in good yields. 3,6-Dinitro-2-tri
- Korotaev, Vladislav Yu.,Sosnovskikh, Vyacheslav Ya.,Barabanov, Mikhail A.,Yasnova, Evgeniya S.,Ezhikova, Marina A.,Kodess, Mikhail I.,Slepukhin, Pavel A.
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- Synthesis of 3-substituted 2-trifluoro(trichloro)methyl-2H-chromenes by reaction of salicylaldehydes with activated trihalomethyl alkenes
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The reaction of activated trihalomethylsubstituted alkenes with salicylaldehydes in the presence of triethylamine gives 3-substituted 2-trifluoromethylchroman-4-ols and 2-trifluoro(trichloro)methyl-2H-chromenes in high yields.
- Korotaev, Vladislav Yu,Kutyashev, Igor B.,Sosnovskikh, Vyacheslav Ya.
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- 3-Nitro-2-trifluoromethyl-2H-chromenes and products of their reduction. Synthesis and cytotoxicity evaluation
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A series of 3-nitro-2-trifluoromethyl-2H-chromenes was synthesized by the reactions of salicylaldehyde derivatives with 3,3,3-trifluoro-1-nitroprop-1-ene. Further transformations of the synthesized chromenes gave hitherto unknown 3-amino-2-trifluoromethylchromanes promising as precursors for the synthesis of fused heterocyclic systems. Cytotoxicity assay first revealed the pronounced activity of several 2-nitro-2-trifluoromethyl-2H-chromenes against human tumor cell lines.
- Baryshnikova,Volkonskii, A. Yu.,Gusev,Labodneva,Sigan,Yakunina,Chkanikov
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- A regio- and stereocontrolled approach to the synthesis of 4-CF3-substituted spiro[chromeno[3,4-c]pyrrolidine-oxindoles] via reversible [3+2] cycloaddition of azomethine ylides generated from isatins and sarcosine to 3-nitro-2-(trifluoromethyl)-2H-chromenes
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A one-pot three-component reaction of azomethine ylides generated in situ from isatins and sarcosine with 3-nitro-2-(trifluoromethyl)-2H-chromenes in i-PrOH at 55-60 °C leads to the kinetically controlled products-exo-spiro[chromeno[3,4-c]pyrrolidine-3,3′-oxindoles]. When this reaction is carried out in 1,4-dioxane under reflux, the thermodynamically controlled endo-spiro[chromeno[3,4-c]pyrrolidine-1,3′-oxindoles] are preferably formed. The isomerization of the kinetic products in DMSO solution at different temperatures has been studied by NMR spectroscopy and the stepwise mechanism of reversible [3+2] cycloaddition has been confirmed. The cytotoxic activity of some CF3-substituted spiro[chromeno[3,4-c]pyrrolidine-oxindoles] against the HeLa cell line was evaluated by the MTT test.
- Kutyashev, Igor B.,Ulitko, Maria V.,Barkov, Alexey Yu.,Zimnitskiy, Nikolay S.,Korotaev, Vladislav Yu.,Sosnovskikh, Vyacheslav Ya.
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p. 18495 - 18504
(2019/12/09)
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- 2-Substituted 3-nitro-2H-chromenes in reaction with azomethine ylide derived from ninhydrin and proline: regio- and stereoselective synthesis of spiro[chromeno[3,4-a]pyrrolizidine-11,2'-indene]-1',3'-diones
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Regio- and stereoselective 1,3-dipolar cycloaddition of stabilized azomethine ylides, generated in situ from ninhydrin and proline, occurred at the double bond activated by nitro group in 3-nitro-2-(trifluoromethyl)- and 3-nitro-2-phenyl-2H-chromenes upon heating in ethanol. This reaction produced high yields of spiro[chromeno[3,4-a]pyrrolizidine-11,2'-indene]-1',3'-diones. The structure of the obtained products was confirmed by the method of X-ray crystallography.
- Korotaev, Vladislav Yu.,Kutyashev, Igor B.,Barkov, Alexey Yu.,Sosnovskikh, Vyacheslav Ya.
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p. 1192 - 1198
(2018/01/11)
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- Highly diastereoselective synthesis of novel 2,3,4-trisubstituted chromanes via the reaction of 3-nitro-2-(trihalomethyl)- and 3-nitro-2-phenyl-2H-chromenes with 1-morpholinocyclopentene
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The reaction of 3-nitro-2-trifluoro(trichloro)methyl- and 3-nitro-2-phenyl-2H-chromenes with 1-morpholinocyclopentene under the conditions of kinetic or thermodynamic control led to the formation of products due to enamine addition at the C-4 atom of chro
- Korotaev, Vladislav Y.,Kutyashev, Igor B.,Barkov, Alexey Y.,Sosnovskikh, Vyacheslav Y.
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p. 5122 - 5137
(2017/07/28)
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