324738-51-4Relevant academic research and scientific papers
Indazole 2-oxides compound and method for preparing indazole 2-oxides compound for providing a nitrogen heterocyclic compound used as a precursor for drugs
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Paragraph 0017; 0019, (2019/08/28)
Provided is a method for preparing an indazole 2-oxides compound, which comprises the step of: performing a cyclization reaction on 2-alkynyl aniline compound and tert-butylnitrite represented by formula (1) in the presence of bis(dibenzylideneacetone) palladium so as to produce an indazole 2-oxides compound, in which, in the formulae (1) and (2), R1 , R2 , R3 and R4 are each hydrogen, halogen or alkyl group; X1 represents an alkyl group, a first chemical structure, a second chemical structure or a third chemical structure where T1 , T2 , T3 , T4 and T5 are each hydrogen, halogen, alkoxy group, or alkyl group; X2 represents hydrogen, cycloalkyl group, alkyl group, alkenyl group, thienyl group, unsubstituted phenyl group, or substituted phenyl group, where the substituent is selected from the group consisting of an alkyl group, an alkoxy group, a halogen, a haloalkyl group, -CN, or -NO2.
Photoinduced synthesis of fluorinated dibenz[: B, e] azepines via radical triggered cyclization
Qi, Xu-Kuan,Zhang, Hong,Pan, Zi-Tong,Liang, Rong-Bin,Zhu, Can-Ming,Li, Jing-Hong,Tong, Qing-Xiao,Gao, Xue-Wang,Wu, Li-Zhu,Zhong, Jian-Ji
supporting information, p. 10848 - 10851 (2019/09/18)
A simple, mild and efficient approach to access fluorinated dibenz[b,e]azepines via visible-light photoredox catalysis is presented. Inexpensive and commercially available fluoroalkyl anhydrides in concert with pyridine N-oxide are employed as the source
Enantioselective A3-Coupling Reaction Employing Chiral CuI-i PrpyboxdiPh/ N-Boc-(l)-Proline Complex under Cooperative Catalysis: Application in the Synthesis of (Indol-2-yl)methanamines
Dhanasekaran, Sivasankaran,Kannaujiya, Vinod. K.,Biswas, Rayhan G.,Singh, Vinod K.
, p. 3275 - 3292 (2019/03/11)
An efficient route to enantioenriched propargylamines via a three-component alkynylation reaction using cooperative catalysis with a CuI-iPrpyboxdiPh complex and N-Boc-(l)-proline has been accomplished. A variety of functionalized amines, aldehydes, and 2-ethynyl anilines were reacted smoothly at ambient temperature to furnish a wide range of propargylamines in high yields (up to 94%) and excellent enantioselectivities (up to 98% ee). Synthetic utility of the methodology has been demonstrated by transforming the products into various synthetically useful intermediates. Finally, propargylamines were transformed into biologically important (indol-2-yl)methanamines over two steps in good yields (up to 88%) with an excellent level of enantioselectivities (up to 95%).
Electrochemical Difluoromethylarylation of Alkynes
Xiong, Peng,Xu, He-Huan,Song, Jinshuai,Xu, Hai-Chao
supporting information, p. 2460 - 2464 (2018/02/28)
An unprecedented radical difluoromethylarylation reaction of alkynes has been developed by discovering a new difluoromethylation reagent, CF2HSO2NHNHBoc. This air-stable and solid reagent can be prepared in one step from commercially available reagents CF2HSO2Cl and NH2NHBoc. The CF2H radical, generated through ferrocene-mediated electrochemical oxidation, participates in an unexplored alkyne addition reaction followed by a challenging 7-membered ring-forming homolytic aromatic substitution step to afford fluorinated dibenzazepines.
Bis(dibenzylideneacetone)palladium(0)/tert-Butyl Nitrite- Catalyzed Cyclization of o-Alkynylanilines with tert-Butyl Nitrite: Synthesis and Applications of Indazole 2-Oxides
Senadi, Gopal Chandru,Wang, Ji-Qi,Gore, Babasaheb Sopan,Wang, Jeh-Jeng
supporting information, p. 2747 - 2753 (2017/08/23)
An efficient method for the synthesis of 1-benzyl/arylindazole 2-oxides via a bis(dibenzylideneacetone)palladium(0) [Pd(dba)2]/tert-butyl nitrite (TBN)-catalyzed reaction of o-alkynylaniline derivatives with TBN is reported. The overall transfo
Stereoselective Synthesis of Methylene Oxindoles via Palladium(II)-Catalyzed Intramolecular Cross-Coupling of Carbamoyl Chlorides
Le, Christine M.,Sperger, Theresa,Fu, Rui,Hou, Xiao,Lim, Yong Hwan,Schoenebeck, Franziska,Lautens, Mark
supporting information, p. 14441 - 14448 (2016/11/13)
We report a highly robust, general and stereoselective method for the synthesis of 3-(chloromethylene)oxindoles from alkyne-tethered carbamoyl chlorides using PdCl2(PhCN)2 as the catalyst. The transformation involves a stereo- and regioselective chloropalladation of an internal alkyne to generate a nucleophilic vinyl PdII species, which then undergoes an intramolecular cross-coupling with a carbamoyl chloride. The reaction proceeds under mild conditions, is insensitive to the presence of moisture and air, and is readily scalable. The products obtained from this reaction are formed with >95:5 Z:E selectivity in nearly all cases and can be used to access biologically relevant oxindole cores. Through combined experimental and computational studies, we provide insight into stereo- and regioselectivity of the chloropalladation step, as well as the mechanism for the C-C bond forming process. Calculations provide support for a mechanism involving oxidative addition into the carbamoyl chloride bond to generate a high valent PdIV species, which then undergoes facile C-C reductive elimination to form the final product. Overall, the transformation constitutes a formal PdII-catalyzed intramolecular alkyne chlorocarbamoylation reaction.
An efficient approach to 1,2,3-trisubstituted indole via rhodium catalyzed carbene Csp3-H bond insertion
Shen, Mei-Hua,Pan, Ying-Peng,Jia, Zhi-Hong,Ren, Xin-Tao,Zhang, Ping,Xu, Hua-Dong
supporting information, p. 4851 - 4854 (2015/05/05)
A method for convenient synthesis of N-alkyl-2-aryl-indole-3-carbaldehyde has been described. A variety of highly valuable indolyl aldehydes have been prepared through this method. Electron donating groups on both aromatic rings (anilinyl and benzyl) facilitate the formation of the desired products. A benzylic C-H insertion by rhodium carbene is the key step for this transformation. This journal is
Preparation of triazoloindoles via tandem copper catalysis and their utility as α-imino rhodium carbene precursors
Xing, Yanpeng,Sheng, Guorong,Wang, Jing,Lu, Ping,Wang, Yanguang
supporting information, p. 1244 - 1247 (2014/03/21)
3-Sulfonyl[1,2,3]triazolo[4,5-b]indoles were efficiently prepared via a tandem catalysis process involving intramolecular ligand stabilized CuAAC and Cu-catalyzed C-N coupling. The obtained 3-sulfonyl[1,2,3]triazolo[4,5-b]indoles could be utilized as α-im
Pd(ii)-catalyzed ligand controlled synthesis of methyl 1-benzyl-1H-indole- 3-carboxylates and bis(1-benzyl-1H-indol-3-yl)methanones
Shen, Rong,Kusakabe, Taichi,Takahashi, Keisuke,Kato, Keisuke
supporting information, p. 4602 - 4609 (2014/06/24)
A simple change of ligand and solvent allows controlled, effective switching between cyclization-carbonylation and cyclization-carbonylation- cyclization-coupling (CCC-coupling) reactions of 2-alkynylanilines catalyzed by palladium(ii). The use of a [Pd(tfa)2(box)] catalyst in iPrOH afforded symmetrical ketones bearing two indoles in good yields; replacing the catalyst and solvent with Pd(tfa)2 and DMSO-MeOH led to the formation of methyl 1-benzyl-1H-indole-3-carboxylates in good yields. This journal is
Intramolecular cyclization of alkynyl α-ketoanilide utilizing [1,2]-phospha-brook rearrangement catalyzed by phosphazene base
Kondoh, Azusa,Aoki, Takuma,Terada, Masahiro
supporting information, p. 3528 - 3531 (2014/07/21)
A novel catalytic cyclization reaction of alkynyl α-ketoanilide was developed by utilizing the [1,2]-phospha-Brook rearrangement. This reaction involves the generation of an amide enolate via the umpolung process, that is the addition of dialkyl phosphite to a keto moiety followed by the [1,2]-phospha-Brook rearrangement, and the subsequent intramolecular addition of the enolate to an alkyne to afford 3,4-dihydro-2-quinolone derivatives. Under high-temperature reaction conditions, further rearrangement of the allylic phosphate moiety occurs to provide 2-quinolone derivatives.
