64648-65-3Relevant academic research and scientific papers
Synthesis of indolo[2,1-: A] isoquinoline derivatives via visible-light-induced radical cascade cyclization reactions
Wei, Yun-Long,Chen, Jian-Qiang,Sun, Bo,Xu, Peng-Fei
supporting information, p. 5922 - 5925 (2019/05/27)
We describe a photocatalyzed transformation for the synthesis of the indolo[2,1-a]isoquinoline core structure. This redox neutral reaction features mild reaction conditions and exceptional functional group tolerance. A series of valuable indolo[2,1-a]isoquinoline derivatives bearing various functional groups were synthesized using this method in good to excellent yields.
Thermal and spectroscopic studies of 2,3,5-trisubstituted and 1,2,3,5-tetrasubstituted indoles as non-competitive antagonists of GluK1/GluK2 receptors
Bartyzel, Agata,Kaczor, Agnieszka A.,G?uchowska, Halina,Pitucha, Monika,Wróbel, Tomasz M.,Matosiuk, Dariusz
, p. 935 - 944 (2018/03/21)
This paper reports the thermal stability and thermal degradation of six derivatives of indole by means of TG-DSC (in air) and TG-FTIR (in nitrogen) techniques. The compounds were also characterized by infrared spectroscopy. In addition, IR spectra were ca
A Convenient Modification of the Fischer Indole Synthesis with a Solid Acid
Chandrasekhar, Sosale,Mukherjee, Somnath
supporting information, p. 1018 - 1022 (2015/03/30)
(Chemical Equation Presented). A new one-pot version of the titled reaction involves heating a mixture of a carbonyl compound, a phenylhydrazine, and the cation exchange resin Amberlite IR 120 in refluxing ethanol. A variety of enolizable aldehydes, and ketones and several substituted phenylhydrazines could thus be converted to the corresponding indoles in excellent yields (70-88%). Reaction times were typically 6-10 h, with the resin being then filtered off and the product isolated after minimal workup.
Regioselective synthesis of indoles via rhodium-catalyzed C-H activation directed by an in-situ generated redox-neutral group
Muralirajan, Krishnamoorthy,Cheng, Chien-Hong
, p. 1571 - 1576 (2014/06/09)
A regioselective synthesis of indoles from arylhydrazine hydrochlorides with alkynes and diethyl ketone catalyzed by a rhodium complex is described. A possible mechanism involving an in-situ generated oxidizing directing group -N-Ni'CR1R2 assisted ortho-C-H activation and reductive elimination are proposed. The catalytic reaction is highly compatible with a wide range of functional arylhydrazines and alkynes. The reaction proceeds under mild reaction conditions and is atom-step economical.
Structural studies, homology modeling and molecular docking of novel non-competitive antagonists of GluK1/GluK2 receptors
Kaczor, Agnieszka A.,Karczmarzyk, Zbigniew,Fruziński, Andrzej,Pihlaja, Kalevi,Sinkkonen, Jari,Wiin?maki, Kirsti,Kronbach, Christiane,Unverferth, Klaus,Poso, Antti,Matosiuk, Dariusz
, p. 787 - 795 (2014/01/23)
Non-competitive ligands of kainate receptors have focused significant attention as medicinal compounds because they seem to be better tolerated than competitive antagonists and uncompetitive blocker of these receptors. Here we present structural studies (
Novel non-competitive antagonists of kainate GluK1/GluK2 receptors
Kaczor, Agnieszka Anna,Kronbach, Christiane,Unverferth, Klaus,Pihlaja, Kalevi,Wiinam?ki, Kirsti,Sinkkonen, Jari,Kijkowska-Murak, Urszula,Wróbel, Tomasz,Stacha, Tomasz,Matosiuk, Dariusz
, p. 891 - 898 (2013/02/22)
A series of 2,3,5-trisubstituted and 1,2,3,5-tetrasubstituted indoles is synthesized by Fisher or Bischler method, followed by alkylation with an appropriate alkyl or aryl halide. Two compounds exhibit non-competitive antagonism towards GluK1 and six - towards GluK2 receptor. The values of IC 50 are in micromolar range. The investigated compounds belong to the most active GluK1 non-competitive inhibitors and are the first known negative allosteric modulators of GluK2 receptor. The observed pattern of activity is rationalized by molecular modelling, in particular by construction of the pharmacophore model.
One-pot-one-step, microwave-assisted Fischer indole synthesis
Creencia, Evelyn Cuevas,Tsukamoto, Masayuki,Horaguchi, Takaaki
experimental part, p. 1095 - 1102 (2011/11/04)
The Fischer indole synthesis was carried out using microwaves instead of conventional heating procedures. When the mixture of phenylhydrazine, cyclohexanone and zinc chloride was irradiated at 600 W for 3 min, 76% of 1,2,3,4-tetrahydrocarbazole was obtained. However, when zinc chloride was replaced with p-toluenesulfonic acid (p-TSA), the reaction yielded 91% of 1,2,3,4-tetrahydrocarbazole. Thus, a series of indoles were prepared using microwaves in the presence of p-TSA catalyst.
Indole synthesis via rhodium catalyzed oxidative coupling of acetanilides and internal alkynes
Stuart, David R.,Bertrand-Laperle, Megan,Burgess, Kevin M. N.,Fagnou, Keith
supporting information; experimental part, p. 16474 - 16475 (2009/04/13)
The oxidative synthesis of highly functionalized indoles from simple anilines and internal alkynes mediated by a rhodium(III) catalyst is described. Good yields are obtained for a variety of aniline substrates, and good regioselectivity is obtained for the more sterically accessible position when meta-substituted anilines are used. Symmetrical and unsymmetrical alkynes react efficiently with high (>40:1) C2/C3 regioselectivity when aryl/alkyl substituted alkynes are used. Copyright
Oxidative cleavage reaction of substituted indoles catalyzed by plant cell cultures
Takemoto, Masumi,Iwakiri, Yasutaka,Tanaka, Kiyoshi
, p. 373 - 383 (2008/03/12)
We have developed a novel method for the oxidative cleavage of indole carbon double bonds in the presence of H2O2 using plant cell cultures as peroxidase. The oxidative method has some advantage, as features such as mild reactions, good yields, easy work-up and safety.
Preparation of Quinone Imine Ketals via Intramolecular Condensation of Amino-Substituted Quinone Monoketals. Anodic Oxidation Chemistry of Trifluoracetamide Derivatives of 1,4-Dimethoxybenzenes and 4-Methoxyphenols
Swenton, John S.,Shih, Chuan,Chen, Chung-Pin,Chou, Chun-Tzer
, p. 2019 - 2026 (2007/10/02)
Two routes have been developed to the previously unknown quinone imine ketal moiety.One involves a sequence of anodic oxidation of the N-trifluoroacetamide of a 2-(2,5-dimethoxyphenyl)ethylamine or 3-(2,5-dimethoxyphenyl)propylamine derivative to form the respective quinone bisketal followed by basic hydrolysis of the trifluoroacetamide linkage, acidic hydrolysis of the quinone bisketal to a quinone monoketal, and intramolecular condensation to form the quinone imine ketal.This method reuires an additional substituent at the 4-position (bromine or methoxy) to direct the regiochemistry of the quinone bisketal hydrolysis.The second method involves similar chemistry except that the anodic oxidation of a 4-methoxyphenol derivative directly affords the quinone monoketal.Hydrolysis of the trifluoroacetamide followed by an intramolecular condensation reaction affords the quinone imine ketal.Selected aspects of the chemistry of these compounds have been studied.Especially interesting is the reaction of a model quinone imine ketal with organolithium reagents.Either 1- or 2-substituted-5-methoxyindole is produced, depending upon the organolithium compound.
