719-64-2Relevant academic research and scientific papers
Cooperative Co(III)/Cu(II)-Catalyzed C-N/N-N Coupling of Imidates with Anthranils: Access to 1H-Indazoles via C-H Activation
Li, Lei,Wang, He,Yu, Songjie,Yang, Xifa,Li, Xingwei
, p. 3662 - 3665 (2016)
Cooperative cobalt- and copper-catalyzed C-H activation of imidate esters and oxidative coupling with anthranils allowed efficient synthesis of 1H-indazoles in the absence of metal oxidants. The anthranil acts as a convenient aminating reagent as well as an organic oxidant in this transformation. The copper catalyst likely functions at the stage of N-N formation.
Metal-Free Synthesis of Anthranils by PhIO Mediated Heterocyclization of ortho-Carbonyl Anilines
Garia, Alankrita,Grover, Jatin,Jain, Nidhi
, p. 4125 - 4131 (2021/08/24)
Here, we report a metal-free synthesis of anthranils from ortho-carbonyl anilines using PhIO as a sole additive under ambient conditions. This methodology did not require any external additives and delivered anthranils in excellent yields with broad substrate scope. The mechanistic studies suggest that the reaction proceeds via in-situ generation of iminoiodane leading to nitrene and a subsequent nucleophilic attack from oxygen of ortho-carbonyl aniline on nitrene results in heterocyclization.
Practical Synthesis of Benzimidazo[1,2- A[quinolines via Rh(III)-Catalyzed C-H Activation Cascade Reaction from Imidamides and Anthranils
Hu, Yao,Wang, Ting,Liu, Yanzhao,Nie, Ruifang,Yang, Ninghong,Wang, Qiantao,Li, Guo-Bo,Wu, Yong
supporting information, p. 501 - 504 (2020/01/31)
We report a novel and practical one-pot Rh(III)-catalyzed strategy to construct benzimidazo[1,2-a]quinolines from readily available imidamides and anthranils. The cascade reaction proceeds via a C-H amination-cyclization-cyclization process in ionic liquid without any additives and possesses simple operation, moderate-to-high yield, and broad substrate scope features, which will provide the reference for the construction of biologically active fused benzimidazoles.
Rh(iii)-Catalyzed tandem indole C4-arylamination/annulation with anthranils: Access to indoloquinolines and their application in photophysical studies
Biswas, Aniruddha,Bera, Satabdi,Poddar, Puja,Dhara, Dibakar,Samanta, Rajarshi
supporting information, p. 1440 - 1443 (2020/02/11)
An efficient Rh(iii)-catalyzed straightforward strategy was developed for the tandem C4 arylamination/annulation of indole derivatives with anthranil to provide indoloquinoline moieties. This method is simple and regioselective with a wide scope and functional group tolerance. Mechanistic studies revealed the important role of the newly installed azacycle in the conversion of O-protected aldoximes to their cyano derivatives. Studies were carried out to explore the promising photophysical properties of the obtained indoloquinoline derivatives.
RhIII-Catalyzed Straightforward Synthesis of Benzophenanthroline and Benzophenanthrolinone Derivatives using Anthranils
Biswas, Aniruddha,Sarkar, Souradip,Samanta, Rajarshi
supporting information, p. 3000 - 3004 (2019/02/13)
An efficient pot-economic and step-economic RhIII-catalyzed site-selective direct amination/annulation strategy was developed for the synthesis of benzophenanthroline derivatives using quinoline N-oxides and anthranils. The method was further extended to the synthesis of nitrogen-containing extended π-conjugated benzophenanthrolinone derivatives. Late-stage functionalizations of cinchonidine and cinchophen derivatives and synthesis of a bioactive quinolino-indole were achieved.
Gold(III)-catalyzed chemoselective annulations of anthranils with N-allylynamides for the synthesis of 3-azabicyclo[3.1.0]hexan-2-imines
Song, Lina,Tian, Xianhai,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
supporting information, p. 9007 - 9010 (2019/08/01)
We herein report the gold(iii)-catalyzed selective annulation of anthranils with N-allylynamides under mild conditions. By trapping the in situ-generated α-imino gold carbenes, 3-azabicyclo[3.1.0]hexan-2-imines were obtained in high synthetic efficiency. The reaction, which can be conducted in the gram scale, tolerates electron-rich and electron-deficient anthranils as well as a diverse set of functionalized ynamides (aryl- and alkyl-substituted terminal).
Catalyst-free cyclization of anthranils and cyclic amines: One-step synthesis of rutaecarpine
Li, Jian,Wang, Zheng-Bing,Xu, Yue,Lu, Xue-Chen,Zhu, Shang-Rong,Liu, Li
supporting information, p. 12072 - 12075 (2019/10/14)
An efficient synthesis of a variety of quinazolinone derivatives via a direct cyclization reaction between commercially available anthranils and cyclic amines is described. The developed transformation proceeds with the merits of high step- and atom-efficiency, a broad substrate scope, and good to excellent yields, without additional catalysts, and offers a practical way for the preparation of rutaecarpine and its derivatives with structural diversity.
Preparation method of alprazolam intermediate
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Paragraph 0030; 0032; 0033; 0036; 0040, (2018/07/30)
The invention discloses a preparation method of an alprazolam intermediate. The method comprises the following steps: sequentially adding methanol and p-nitrochlorobenzene in a sodium hydroxide watersolution, dropwise adding phenylacetonitrile under stirring, reacting at 40 +/-5 DEG C after the dropwise addition is finished, and carrying out post-treatment to obtain an intermediate (II) ; and dissolving the intermediate (II) in ethanol, adding iron powder, refluxing, dropwise adding sulfuric acid, refluxing for 1 hour, and carrying out post-treatment to obtain an intermediate(III). Accordingto the method disclosed by the invention, the sodium hydroxide water solution is used in the synthesis of the intermediate (II) to replace a dangerous mode of refluxing and dissolving solid sodium hydroxide by using ethanol, a small amount of methanol is added into the reaction system, and the problem of two-phase reaction is successfully solved. The sulfuric acid is used for replacing volatile hydrochloric acid during the synthesis of the intermediate (III), the reaction time is effectively shortened, and the reaction efficiency is improved. The method disclosed by the invention is safer to operate, short in reaction time and more suitable for industrial production.
Preparation method of 2-amino-5- chlorobenzophenone
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Paragraph 0014; 0015; 0016; 0017, (2018/03/26)
The invention discloses a preparation method of 2-amino-5- chlorobenzophenone. The preparation method comprises the following steps: (1) mixing ethanol with the mass concentration of 95%, sodium hydroxide, parachloronitrobenzene and benzyl cyanide, mixing the mixture and performing ultrasonic oscillation on the mixture at the temperature of 25-35 DEG C for 1h; (2) performing microwave heating on aproduct obtained in step (1) for 10min, adding water in a system, filtering, washing filter residues with methanol three times and drying the filter residues, so as to obtain 5-chlorine-3-phenyl-2, 1-benzisoxazole; (3) mixing methanol, the 5-chlorine-3-phenyl-2, 1-benzisoxazole, a palladium carbon catalyst and ammonium formate, heating and refluxing for 2h, cooling to room temperature, filteringand performing vacuum drying on the filter residues. The method provided by the invention is high in product yield, short in reaction time and less in waste discharge and is environmentally friendly.
Preparation method of 2-amino-5-chlorobenzophenone
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Paragraph 0014; 0015; 0016, (2018/03/26)
The invention discloses a preparation method of 2-amino-5-chlorobenzophenone. The preparation method of 2-amino-5-chlorobenzophenone comprises the following steps: (1) mixing ethanol and sodium hydroxide, performing heating reflux, adding parachloronitrobenzene, stirring for 30 to 60 minutes, cooling to 28 DEG C, adding benzyl cyanide, reacting at 25 to 35 DEG C for 3 hours and naturally cooling to room temperature; (2) performing microwave heating, adding water, filtering, washing the filter residue with methanol and drying to obtain 5-chlorine-3-phenyl-2,1 benzisoxazole; and (3) performing heating reflux on 5-chlorine-3-phenyl-2,1 benzisoxazole, iron powder and ethanol, dropwise adding a hydrochloric acid ethanol solution into a system, refluxing at 35 DEG C for 2 hours, adjusting the pHof the system to be 7 to 8, adding activated carbon into the system, continuously refluxing, filtering and vacuum-drying the filter residue to obtain 2-amino-5-chlorobenzophenone. By the method, theyield of products is high and can reach to 94 percent, the reaction time is short, emission of waste is reduced, and the production method is environment-friendly.
