5176-14-7Relevant academic research and scientific papers
Metal-Free [3+2] Annulation of Ynamides with Anthranils to Construct 2-Aminoindoles
Zhang, Jingyi,Li, Ying,Zhang, Chaofeng,Wang, Xiao-Na,Chang, Junbiao
supporting information, p. 2029 - 2035 (2021/04/05)
A novel metal-free [3+2] annulation of ynamides with anthranils provides a facile, flexible, environmentally friendly, and atom-economical route to 2-aminoindoles. This synthetic process proceeds with efficiency, excellent regioselectivity, and wide functional group tolerance under mild conditions. Moreover, the obtained 2-aminoindole products represent a multifunctional platform for the construction of various 2-aminoindolyl frameworks.
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.
TfOH-Promoted Decyanative Cyclization toward the Synthesis of 2,1-Benzisoxazoles
Zhang, Mengge,Meng, Yonggang,Wu, Yangang,Song, Chuanjun
, p. 7326 - 7332 (2021/06/25)
A novel solvent-free, TfOH-promoted decyanative cyclization approach for the synthesis of 2,1-benzisoxazoles has been developed. The reactions are complete instantly at room temperature and result in the formation of the desired 2,1-benzisoxazoles in a 34-97% isolated yield.
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.
Metal-Free, Visible-Light-Enabled Direct C3-H Arylation of Anthranils
Adak, Tapas,Hashmi, A. Stephen K.,Hu, Chao,Li, Jun,Rudolph, Matthias
supporting information, (2020/07/24)
An eosin Y disodium salt-catalyzed photoredox C-H arylation of anthranils is reported. A variety of aryl diazonium tetrafluoroborates were used as aryl sources, providing the C3 cross-coupled products. The in situ generated reactive radicals were trapped by anthranils, providing an alternative method to transition-metal-catalyzed C-H arylations of anthranils. Gold-catalyzed downstream transformations demonstrate the synthetic potential of these valuable building blocks.
Synthesis of 3-phenylbenzo[c]isoxazoles by thermocyclization of 2-azidobenzophenones
Odinokov,Plekhovich,Budruev
, p. 1298 - 1300 (2019/07/15)
3-Phenylbenzo[c]isoxazoles were synthesized by non-catalytic thermolysis of 2-azidobenzophenones in dry xylene with quantitative yields. The trace content of water in solvents reduces the yields of the reaction products. 2-Azidobenzoic acid esters are sta
Gold(III)-Catalyzed Site-Selective and Divergent Synthesis of 2-Aminopyrroles and Quinoline-Based Polyazaheterocycles
Zeng, Zhongyi,Jin, Hongming,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
supporting information, p. 16549 - 16553 (2018/11/23)
A facile, site-selective, and divergent approach to construct 2-aminopyrroles and quinoline-fused polyazaheterocycles enabled by a simple gold(III) catalyst from ynamides and anthranils under mild reaction conditions is described. This one-pot strategy uses readily available starting materials, proceeds in a highly step- and atom-economical manner, with broad substrate scope and scale-up potential. The key element for success in this tandem reaction is a catalyst-directed preferred quenching of the in situ generated gold carbene intermediates by a nucleophilic benzyl/2-furylmethyl moiety on the ynamides as an alternative to the known C?H annulation leading to indoles.
Cp*RhIII-Catalyzed Directed Amidation of Aldehydes with Anthranils
Debbarma, Suvankar,Sudan Maji, Modhu
, p. 3699 - 3706 (2017/07/22)
An approach towards construction of amide C–N bonds under mild conditions through rhodium(III) catalysis has been explored. Previous waste-free amidations were generally limited to the condensation of carboxylic acids and amines. In this report, we directly applied amination of the aldehyde C(sp2)–H bond to extend the scope of amidation reactions. The amination shows a wide substrates scope, and several important functional groups were tolerated under the benign reaction conditions. The synthesized amides are important precursors for the preparation of benzoxazinone derivatives, found in various bioactive natural products.q.
Gold-Catalyzed C-H Annulation of Anthranils with Alkynes: A Facile, Flexible, and Atom-Economical Synthesis of Unprotected 7-Acylindoles
Jin, Hongming,Huang, Long,Xie, Jin,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
supporting information, p. 794 - 797 (2016/02/27)
The gold-catalyzed C-H annulation of anthranil derivatives with alkynes offers a facile, flexible, and atom-economical one-step route to unprotected 7-acylindoles. An intermediate α-imino gold carbene, generated by an intermolecular reaction, promotes ortho-aryl C-H functionalization to afford the target products. The transformation proceeds with a broad range of substrates under mild conditions. Moreover, the obtained functionalized indole products represent a versatile platform for the construction of diverse indolyl frameworks.
Synthesis of 3-Substituted 2,1-Benzisoxazoles by the Oxidative Cyclization of 2-Aminoacylbenzenes with Oxone
Chiarini, Marco,Del Vecchio, Luana,Marinelli, Fabio,Rossi, Leucio,Arcadi, Antonio
, p. 3017 - 3030 (2016/10/12)
An efficient approach to the synthesis of 2,1-benzisoxazoles through direct construction of the N-O bond by the chemoselective oxidation of 2-aminoacylbenzenes with Oxone is described. This alternative methodology is characterized by its simple and transition-metal-free conditions and good functional group compatibility utilizing Oxone as a green oxidant instead of hypervalent iodine compounds. Moreover, this new procedure simplifies the number of steps compared to the previously reported procedure by circumventing the use of 2-azido-substituted aryl ketones.
