69511-65-5Relevant academic research and scientific papers
Unexpected cyclization ofortho-nitrochalcones into 2-alkylideneindolin-3-ones
Aksenov, Alexander V.,Aksenov, Dmitrii A.,Aksenov, Nicolai A.,Aksenova, Daria S.,Arutiunov, Nikolai A.,Rubin, Michael
, p. 18440 - 18450 (2020/06/08)
An original, facile, and highly efficient method for the preparation of 2-(3-oxoindolin-2-ylidene)acetonitriles fromortho-nitrochalcones is described. The featured transformation is a triggered Michael addition of the cyanide anion to the chalcone followed by a cascade cyclization mechanistically related to the Baeyer-Drewson reaction.
Synthesis of 2-(1h-indol-2-yl)acetamides via br?nsted acid-assisted cyclization cascade
Aksenov, Alexander V.,Aksenov, Dmitrii A.,Aksenov, Nicolai A.,Griaznov, Georgii D.,Prityko, Lidiya A.,Rubin, Michael,Skomorokhov, Anton A.
, p. 12128 - 12146 (2020/11/10)
An efficient and straightforward Br?nsted-acid mediated cascade process was developed, involving cyclization of readily available β-ketonitriles into 2-aminofurans, and their subsequent recyclization into 2-(1H-indol-2-yl)acetamides is developed. This synthetic route opens a new avenue for an expeditious assembly of various isotryptamine derivatives for medicinal chemistry.
One-Pot Synthesis of Functionalized Carbazoles via a CAN-Catalyzed Multicomponent Process Comprising a C-H Activation Step
González, Juan F.,Rocchi, Damiano,Tejero, Tomás,Merino, Pedro,Menéndez, J. Carlos
supporting information, p. 7492 - 7502 (2017/07/26)
The microwave-promoted three-component reaction between o-nitrochalcones, primary amines and β-dicarbonyl compounds in the presence of Ce(IV) ammonium nitrate constitutes the first example of a multicomponent carbazole synthesis. This reaction furnishes highly substituted and functionalized carbazole derivatives via a double annulation process that generates two C-C and two C-N bonds, with water as the only side product. Mechanistically, this transformation has some unusual features that include an intramolecular coupled hydrogenation-dehydrogenation process, the functionalization of a C-H group by direct attack onto a nitrogen function and a CAN-catalyzed reduction via hydride transfer from ethanol. The mechanisms of these reactions were studied with the aid of computational techniques.
Process Intensification with Bifunctional Heterogeneous Catalysts: Selective One-Pot Synthesis of 2′-Aminochalcones
Climent,Corma,Iborra,Martí
, p. 157 - 166 (2015/04/27)
(Chemical Equation Presented) 2′-Aminochalcones of pharmaceutical and commercial interest have been obtained in high yields and selectivities through a one-pot process using a bifunctional heterogeneous catalyst bearing base and metal active sites. This is a physical mixture material formed by a high-surface-area MgO and Pt on TiO2. The process involves as the first step the Claisen-Schmidt condensation between o-nitroacetophenone and benzaldehyde derivatives on the basic catalytic function. This is followed by a chemoselective hydrogenation of the nitro group in the presence of the carbonyl and double-bond carbon-carbon groups within the molecule. Using the bifunctional catalyst and the reaction system proposed here, it is possible to produce, under mild reaction conditions and short reaction times, 2′-aminochalcones with higher yields and selectivities than those obtained by conventional multistep methods.
Synthesis and binding activity of some pyrazolo[1,5-c]quinazolines as tools to verify an optional binding site of a benzodiazepine receptor ligand
Colotta, Vittoria,Catarzi, Daniela,Varano, Flavia,Filacchioni, Guido,Cecchi, Lucia,Galli, Alessandro,Costagli, Chiara
, p. 2915 - 2921 (2007/10/03)
The synthesis and binding activity at the benzodiazepine receptor of some 2-substituted pyrazolo[1,5-c]quinazolines are reported. The structure- activity relationships and in vitro efficacy of the title compounds, which are devoid of the proton acceptor atom at position 1, are similar to those of some previously reported tricyclic heteroaromatic compounds. This suggests that a proton acceptor at position 1 is an optional binding site of a benzodiazepine receptor ligand which only affects potency.
Synthesis and Biological Activity of Some New 10-phenothiazines
Jaiswal, Neelam,Jaiswal, R. K.,Barthwal, J. P.,Kishor, K.
, p. 252 - 253 (2007/10/02)
Fourteen 10-phenothiazines (IV) have been synthesized via condensation of 10-hydrazino-acetylphenothiazine with substituted benzalacetophenones.These compounds inhibit 33-86percent in vitro activity of rat brain pyruvate oxidase and afford protection against pentylenetetrazol induced seizures in albino mice.However, their anticonvulsant properties are found to be independent of their pyruvate oxidase inhibitory activity.
