5027-78-1Relevant academic research and scientific papers
Diastereodirected synthesis of 1-aryl-4-phenyl-β-carbolines
Semenov,Novikov,Smushkevich,Azev,Kachala
, p. 1273 - 1279 (2005)
A diastereodirected Pictet-Spengler reaction has been carried out to give the previously unknown 1-aryl(alkyl)-4-phenyl-β-carbolines and it has been found that all of the β-carbolines diastereomers obtained have predominantly the R*,R*-configuration. The
Diastereotopic synthesis of 1- and 1,1-substituted 4-phenyl-2,3,4,9- tetrahydro-1H-β-carbolines
Semenov,Novikov,Spitsin,Azev,Kachala
, p. 585 - 590 (2004)
A diastereotopic Pictet-Spengler reaction was performed to form previously unknown 1- and 1,1-substituted 4-phenyl-β-carbolines based on β-phenyltryptamine, aldehydes of various structure, and isatins. It has been demonstrated that the predominant diaster
Synthesis of 4-phenyl-1-(2-thienyl)-2,3,4,9-tetrahydro-1H-β-carboline
Semenov,Novikov,Kachala,Azev
, p. 582 - 584 (2006)
The Pictet - Spengler reaction involving β-phenyltryptamine was shown to be diastereo-specific with formation primarily of the (1S*,4R*) diastereomer of 4-phenyl-1-(2-thienyl)-2,3,4,9-tetrahydro-1H-β-carboline, a compound with potential GABA-receptor acti
Diastereoselective synthesis of 1,1-disubstituted 4-phenyl-2,3,4,9- tetrahydrospiro-β-carbolines from β-phenyltryptamine and isatin derivatives
Semenov,Novikov,Azev,Kachala
, p. 988 - 991 (2005)
The reaction of β-phenyltryptamine with isatin derivatives is diastereoselective (de 66-88%) and affords earlier unknown 1,1-disubstituted 4-phenyl-2,3,4,9-tetrahydrospiro-β-carbolines based on phenyltryptamine and isatins. The study by NMR (NOESY) spectr
The base-free van Leusen reaction of cyclic imines on water: Synthesis of N-fused imidazo 6,11-dihydro β-carboline derivatives
Satyam, Killari,Murugesh,Suresh, Surisetti
, p. 5234 - 5238 (2019/06/07)
Construction of imidazoles has been demonstrated on water under base-free conditions. The reaction of dihydro β-carboline imines and p-toluenesulfonylmethyl isocyanides furnished the corresponding substituted N-fused imidazo 6,11-dihydro β-carboline derivatives in very good yields under ambient conditions. The use of deuterium oxide (D2O) as a solvent enabled the incorporation of deuterium isotopes in the imidazole ring.
Green, Catalyst-Free Reaction of Indoles with β-Fluoro-β-nitrostyrenes in Water
Aldoshin, Alexander S.,Tabolin, Andrey A.,Ioffe, Sema L.,Nenajdenko, Valentine G.
, p. 3816 - 3825 (2018/07/31)
The reaction of 2-fluoro-2-nitrostyrenes with various indoles was investigated. We found that the reaction proceeds as a Michael addition in a highly regioselective manner to form 3-(1-aryl-2-fluoro-2-nitroethyl)-1H-indoles. Thus, a green and catalyst-free synthesis of these compounds was developed using water as a reaction medium. The high effectiveness of this approach was demonstrated through the preparation of target products in up to 92 % isolated yield. Subsequent reduction of the nitro group was investigated. We found that due to the instability of the intermediate α-fluoro amines, the reduction led to non-fluorinated tryptamine derivatives.
Friedel-Crafts alkylation reaction with fluorinated alcohols as hydrogen-bond donors and solvents
Tang, Ren-Jin,Milcent, Thierry,Crousse, Benoit
, p. 10314 - 10317 (2018/03/26)
An effective and clean FC alkylation of indoles and electron-rich arenes with β-nitroalkenes in HFIP was reported. The desired products are formed rapidly in excellent yields under mild conditions without the need for any additional catalysts or reagents. Further, this methodology can be applied to one-pot synthesis of biologically active tryptamine derivatives.
Compound and its preparation method and application
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, (2017/10/06)
The invention provides a compound and a preparation method therefore and application thereof. The compound is a compound shown in a formula I or an enantiomer, a diastereoisomer, raceme, pharmaceutically acceptable salt, a crystalline hydrate or a solvate of the compound, wherein R1 is optionally substituted phenyl, R2 is p-methylphenyl and X is C or N. The compound can be used for treating cancer related diseases. The formula I is shown in the description.
Reduction of aromatic and aliphatic nitro groups to anilines and amines with hypophosphites associated with Pd/C
Baron, Marc,Metay, Estelle,Lemaire, Marc,Popowycz, Florence
, p. 1006 - 1015 (2013/07/26)
The reduction of aromatic and aliphatic nitro groups to anilines and amines is performed with good yield and selectivity in short reaction times. A mixture of sodium hypophosphite and phosphinic acid is used in the presence of a heterogeneous catalyst 2.5 mol% of Pd/C (5%) in a biphasic water/2-MeTHF system.
Metal halide hydrates as lewis acid catalysts for the conjugated Friedel-Crafts reactions of indoles and activated olefins
Schwalm, Cristiane S.,Ceschi, Marco Antonio,Russowsky, Dennis
, p. 623 - 636 (2012/01/05)
Metal halide hydrates such as SnCl2·2H2O, MnCl2·4H2O, SrCl2·6H 2O, CrCl2·6H2O, CoCl2· 6H2O e CeCl3·7H2O were investigated as mild Lewis acids catalysts for the conjugate Friedel-Crafts reaction between indoles and activated olefins. The reactions were carried out with aliphatic unsaturated ketones over a period of days at room temperature, while chalcones reacted only under reflux conditions. The reactions with nitrostyrenes were either performed in solvent or under solventless conditions. In all cases reasonable to good yields were obtained. ?2011 Sociedade Brasileira de Qui?mica.
