- 3,3,3-Trifluoro-1-nitropropene as a Novel Trifluoromethyl-Containing Building Block
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Additions of various carbanion nucleophiles to 3,3,3-trifluoro-1-nitropropene (1) proceeded regiospecifically at the C-2 position of 1 to give the corresponding adducts.The nitro group of the adducts, derived from the reactions with acetylacetone and ethyl acetoacetate, was reduced to the corresponding amines, which were cyclized in situ to the 3-(trifluoromethyl)pyrrole derivatives.
- Iwata, Satoru,Ishiguro, Yoshiharu,Utsugi, Masatuka,Mitsuhashi, Keiryo,Tanaka, Kiyoshi
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- 1-Bromo-3,3,3-trifluoro-1-nitropropene: Synthesis and reaction with phenyl azide
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An improved procedure was developed for the synthesis of 3,3,3-trifluoro-1-nitropropene, and a new representative of gem-bromonitroalkenes, 1-bromo-3,3,3-trifluoro-1-nitropropene, was synthesized therefrom. Its reaction with phenyl azide gave a mixture of two regioisomeric 1,2,3-triazoles, from which pure 5-nitro-1-phenyl-4-(trifluoromethyl)-1H-1,2,3-triazole was isolated.
- Anisimova,Slobodchikova,Kuzhaeva,Stukan’,Bagryanskaya, I. Yu.,Berestovitskaya
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- Highly regio- and stereoselective 1,3-dipolar cycloaddition of stabilised azomethine ylides to 3,3,3-trihalogeno-1-nitropropenes: synthesis of trihalomethylated spiro[indoline-3,2′-pyrrolidin]-2-ones and spiro[indoline-3,3′-pyrrolizin]-2-ones
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Reactions of 3,3,3-trihalogen-1-nitropropenes with N-alkyl-α-amino acids (sarcosine, proline) and isatins proceed regio- and diastereoselectively to give a wide range of trihalomethylated spiro[indoline-3,2′-pyrrolidin]-2-ones and spiro[indoline-3,3′-pyrrolizin]-2-ones in good yields as a result of a 1,3-dipolar cycloaddition of the intermediate stabilised azomethine ylide at the double bond of the nitroalkenes.
- Barkov, Alexey Yu.,Zimnitskiy, Nikolay S.,Korotaev, Vladislav Yu.,Kutyashev, Igor B.,Moshkin, Vladimir S.,Sosnovskikh, Vyacheslav Ya.
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- Stereocontrolled Synthesis of ψ[CH(CF3)NH]Gly-Peptides
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(Matrix presented). A novel class of peptidomimetics having a stereogenic [CH(CF3)NH] replacement for a [CONH] peptide bond has been synthesized. The new compounds have been obtained in a stereocontrolled fashion using a kinetically controlled
- Molteni, Marco,Volonterio, Alessandro,Zanda, Matteo
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- Catalytic Asymmetric Construction of Tertiary Carbon Centers Featuring an α-Difluoromethyl Group with CF2H-CH2-NH2as the "building Block"
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We report here for the first time a novel difluoromethylated ketimine building block condensed by thioisatin and difluoroethylamine, offering efficient access to a broad range of enantioenriched products bearing difluoroethylamine units (27 examples, ≤98% yield, >99% ee) in the presence of quinine-derived squaramide. Further transformation of the intermediate would generate a variety of versatile functional blocks like α-difluoromethyl amines, β-amino acid, and β-diamine with retention of the enantiomeric excess at the difluoromethyl-bound carbon.
- Gao, Fengyun,Guo, Yifei,Sun, Mengmeng,Wang, Yalan,Yang, Changyan,Wang, Yuqiang,Wang, Kairong,Yan, Wenjin
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supporting information
p. 2584 - 2589
(2021/04/13)
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- 6,7-DIHYDRO-4H-PYRAZOLO[1,5-A]PYRAZINE COMPOUNDS FOR THE TREATMENT OF INFECTIOUS DISEASES
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The present invention relates to compounds of the formula (I) or pharmaceutically acceptable salts, enantiomer or diastereomer thereof, wherein R1 to R4 are as described above. The compounds may be useful for the treatment or prophylaxis of hepatitis B virus infection.
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Page/Page column 44-45
(2018/03/26)
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- The asymmetric Friedel-Crafts reaction of indoles with fluoroalkylated nitroalkenes catalyzed by chiral phosphoric acid
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The enantioselective Friedel-Crafts fluoroalkylation of indoles with fluoroalkylated nitroalkenes, catalyzed by chiral phosphoric acid is described. The regioselectivity of fluoroalkylated nitroalkenes is a problem worth discussing, and it was found that the carbon atom adjacent to the fluoroalkyl group is more reactive than that adjacent to NO2 group.
- Lin, Jin-Hong,Xiao, Ji-Chang
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supporting information; experimental part
p. 4536 - 4539
(2011/10/09)
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- Ψ[CH(CF3)NH]Gly-peptides: Synthesis and conformation analysis
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Ψ[CH(CF3)NH]Gly peptides, a conceptually new class of peptidomimetics having a stereogenic trifluoroethylamine group as a natural peptide-bond surrogate, have been synthesized by stereoselective addition of α-amino acid esters to trans-3,3,3-tr
- Molteni, Marco,Bellucci, Maria Cristina,Bigotti, Serena,Mazzini, Stefania,Volonterio, Alessandro,Zanda, Matteo
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scheme or table
p. 2286 - 2296
(2009/09/26)
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- New functionalized, differently fluorinated building-blocks via Michael addition to γ-fluoro-α-nitroalkenes
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The Michael addition of ketone-derived enamines, metalated methylene active compounds and N-methyl pyrroles to γ-fluoro-α-nitroalkenes provided in moderate to good isolated yields the corresponding β-fluoroalkyl nitro compounds, which represent new intere
- Molteni, Marco,Consonni, Roberto,Giovenzana, Tommaso,Malpezzi, Luciana,Zanda, Matteo
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p. 901 - 908
(2008/02/10)
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- Investigation of reaction between 2-diazo-3-nitro-1,1,1 -trifluoropropane and ethyl 3-morpholinocrotonate. The problem of existence of trifluoromethylnitromethylcarbene anion
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Reaction of 2-diazo-3-nitro-l,l,l-trifluoropropane with ethyl 3-morpholinocrotonate results in ethyl 2-methyl-2-morpholino-3-nitro-4-trifluoromethylcyclobutanoate. Acidic hydrolysis of the latter compound affords ethyl 2-(2-nitroethyl-l-trifluoroethyl)butanoate-3 occuring as a mixture of enol and two diastereomeric ketone forms. The presumed reaction mechanism includes formation in the presence of a catalytic quantity of base of trifluoromethylnitromethylcarbene anion which reacts by two routes: insertion into the olefin C-H bond of enamine with subsequent cyclization of the intermediate, and carbene-olefin isomerization yielding 3-nitro-l,l,l-trifluoro-2-propene which adds to enamine by Michael reaction.
- Aizikovich,Korotaev,Kodess,Barkov
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p. 1093 - 1098
(2007/10/03)
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