5782-15-0Relevant articles and documents
Synthesis of Ester-Substituted Indolo[2,1-a]isoquinolines via Photocatalyzed Alkoxycarbonylation/Cyclization Reactions
Chen, Jian-Qiang,Tu, Xiaodong,Qin, Binyan,Huang, Shaoxin,Zhang, Jun,Wu, Jie
supporting information, p. 642 - 647 (2022/01/20)
A direct alkoxycarbonylation/cyclization reaction is accomplished under visible light-induced photoredox catalysis. With this approach, a variety of ester-substituted indolo[2,1-a]isoquinolines are prepared in good to excellent yields. It is worth noting that this method not only can afford the synthesis of indolo[2,1-a]isoquinolines but also can provide an alternative route for generating complex target structures bearing carboxylic esters.
Electrochemical Tri- and Difluoromethylation-Triggered Cyclization Accompanied by the Oxidative Cleavage of Indole Derivatives
Yuan, Xin,Cui, Yu-Sheng,Zhang, Xin-Peng,Qin, Long-Zhou,Sun, Qi,Duan, Xiu,Chen, Lin,Li, Guigen,Qiu, Jiang-Kai,Guo, Kai
supporting information, p. 6522 - 6528 (2021/03/16)
Considering their unique roles in organic synthesis, and pharmaceutical and agrochemical applications, the development of fluoroalkylation, cyclization, and indole oxidative cleavage are important topics. Herein, an unprecedented electrochemical tri- and difluoromethylation/cyclization/indole oxidative cleavage process occurring in an undivided cell is presented. The protocol employs a readily prepared Langlois reagent as the fluoroalkyl source, affording a series of tri- or difluoromethylated 2-(2-acetylphenyl)isoquinoline-1,3-diones in good yields with excellent stereoselectivity. It is worth noting that this new methodology merges the fluoroalkylation/cyclization of N-substituted acrylamide alkenes with the oxidative cleavage of an indole C(2)=C(3) bond under external oxidant-free conditions.
Visible-Light Photocatalytic Tri- A nd Difluoroalkylation Cyclizations: Access to a Series of Indole[2,1- A[isoquinoline Derivatives in Continuous Flow
Yuan, Xin,Duan, Xiu,Cui, Yu-Sheng,Sun, Qi,Qin, Long-Zhou,Zhang, Xin-Peng,Liu, Jie,Wu, Meng-Yu,Qiu, Jiang-Kai,Guo, Kai
supporting information, p. 1950 - 1954 (2021/04/05)
A process for achieving photocatalyzed tri- A nd difluoromethylation/cyclizations for constructing a series of tri-or difluoromethylated indole[2,1-a]isoquinoline derivatives is described. This protocol utilized an inexpensive organic photoredox catalyst and provided good yields. Moreover, the combination of continuous flow and photochemistry, designed to provide researchers with a unique green process, was also shown to be key to allowing the reaction to proceed (product yield of 83% in flow vs 0% in batch).
Manganese(iii)-promoted tandem phosphinoylation/cyclization of 2-arylindoles/2-arylbenzimidazoles with disubstituted phosphine oxides
Jiang, Shuai-Shuai,Li, Jin-Heng,Luo, Shu-Zheng,Song, Ren-Jie,Wu, Yan-Chen,Xiao, Yu-Ting
supporting information, p. 4843 - 4847 (2020/07/13)
A simple and practical method for the synthesis of phosphoryl-substituted indolo[2,1-a]isoquinolin-6(5H)-ones and benzimidazo[2,1-a]isoquinolin-6(5H)-ones through manganese(iii)-promoted tandem phosphinoylation/cyclization of 2-arylindoles or 2-arylbenzimidazoles with disubstituted phosphine oxides was developed. In this transformation, new C-P bond and C-C bond were constructed simultaneously under silver-free conditions, exhibiting a broad substrate scope. It was noted that not only diarylphosphine oxides but also dialkyl and arylalkyl-phosphine oxides were compatible with the conditions. This journal is
Organophotocatalytic Arene Functionalization: C-C and C-B Bond Formation
Lee, Da Seul,Kim, Chung Soo,Iqbal, Naila,Park, Gyeong Su,Son, Kyung-Sun,Cho, Eun Jin
supporting information, p. 9950 - 9953 (2019/12/24)
Organophotocatalytic C-C and C-B bond formation reactions of aryl halides have been developed in the presence of an organophotosensitizer, 3,7-di([1,1′-biphenyl]-4-yl)-10-(4-(trifluoromethyl)phenyl)-10H-phenoxazine that has highly negative reduction potential at its photoexcited state. The developed reaction conditions are mild and allow the intermolecular C-C bond formation of the generated aryl radical with electron-rich (hetero)arenes and C-B bond formation with bis(pinacolato)diboron.
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
Mild and selective base-free C-H arylation of heteroarenes: experiment and computation
Gemoets, Hannes P. L.,Kalvet, Indrek,Nyuchev, Alexander V.,Erdmann, Nico,Hessel, Volker,Schoenebeck, Franziska,No?l, Timothy
, p. 1046 - 1055 (2017/02/10)
A mild and selective C-H arylation strategy for indoles, benzofurans and benzothiophenes is described. The arylation method engages aryldiazonium salts as arylating reagents in equimolar amounts. The protocol is operationally simple, base free, moisture tolerant and air tolerant. It utilizes low palladium loadings (0.5 to 2.0 mol% Pd), short reaction times, green solvents (EtOAc/2-MeTHF or MeOH) and is carried out at room temperature, providing a broad substrate scope (47 examples) and excellent selectivity (C-2 arylation for indoles and benzofurans, C-3 arylation for benzothiophenes). Mechanistic experiments and DFT calculations support a Heck-Matsuda type coupling mechanism.
Base-promoted domino reaction for the synthesis of 2,3-disubstituted indoles from 2-aminobenzaldehyde/2-amino aryl ketones, tosylhydrazine, and aromatic aldehydes
Wu, Yan-Dong,Ma, Jun-Rui,Shu, Wen-Ming,Zheng, Kai-Lu,Wu, An-Xin
, p. 4821 - 4826 (2016/07/18)
A base-promoted domino reaction to synthesize the 2,3-disubstituted indoles from 2-aminobenzaldehyde/2-amino aryl ketones, tosylhydrazine, and aromatic aldehydes has been developed. This strategy provides a simple and beneficial way for the construction of 2,3-disubstituted indole compounds from readily available starting materials under mild conditions.
Iron(II) bromide-catalyzed intramolecular c-h bond amination [1,2]-shift tandem reactions of aryl azides
Nguyen, Quyen,Nguyen, Tuyen,Driver, Tom G.
supporting information, p. 620 - 623 (2013/03/13)
Iron(II) bromide catalyzes the transformation of ortho-substituted aryl azides into 2,3-disubstituted indoles through a tandem ethereal C-H bond amination [1,2]-shift reaction. The preference for the 1,2-shift component of the tandem reaction was established to be Me 1 2 Ph.
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.
