- Pd-Catalyzed One-Pot Insertion Reaction of Cyclic C-Acylimines into Carbon-Carbon σ-Bonds for the Synthesis of Polyfunctional Indolin-3-ones from 2-Alkynyl Arylazides and Aryl Ketones
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A method to prepare polyfunctional indolin-3-ones by Pd-catalyzed one-pot insertion reaction of cyclic C-acylimines into carbon-carbon σ-bonds is described. The reaction was accomplished in good to excellent yields under mild reaction conditions. (Figure presented.).
- Li, Ping,Yong, Wanxiong,Sheng, Rong,Rao, Weidong,Zhu, Xinbao,Zhang, Xiaoxiang
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- Palladium-Catalyzed One-Pot Synthesis of C2-Quaternary Indolin-3-ones via 1H-indole-3-sulfonates Generated in Situ from 2-Alkynyl Arylazides and Sulfonic Acids
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A novel method for the synthesis of C2-quaternary indole-3-ones via palladium-catalyzed one-pot transformation of 2-alkynyl arylazides is described. The reaction produced in moderate to excellent yields under mild conditions. This novel rearrangement of 1-H-indole-3-sulfonates represents an important contribution to the application of aryl sulfonates. (Figure presented.).
- Zhang, Xiaoxiang,Li, Ping,Lyu, Chang,Yong, Wanxiong,Li, Jing,Pan, Xinyu,Zhu, Xinbao,Rao, Weidong
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- Ipso-substitution Reactions of 3-Substituted Indoles with Benzoyl t-Butyl Nitroxide
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Reactions between benzoyl t-butyl nitroxide and certain 2-phenylindoles carrying a substituent at C-3 give 2-phenyl-3H-indol-3-one; 2-phenylindole itself gives compound (7).
- Berti, Corrado,Colonna, Martino,Greci, Lucedio,Marchetti, Leonardo,Perkins, M. John
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- One-Pot Asymmetric Oxidative Dearomatization of 2-Substituted Indoles by Merging Transition Metal Catalysis with Organocatalysis to Access C2-Tetrasubstituted Indolin-3-Ones
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A one-pot approach for the asymmetric synthesis of C2-tetrasubstituted indolin-3-ones from 2-substituted indoles was developed via merging transition metal catalysis with organocatalysis. This strategy involves two processes, including CuI catalyzed oxidative dearomatization of 2-substituted indoles using O2 as green oxidant, and followed by an proline-promoted asymmetric Mannich reaction with ketones or aldehydes. A series of C2-tetrasubstituted indolin-3-ones were obtained in 35–86% yields, 2:1->20:1 dr and 48–99% ee. Moreover, the synthetic 2-tetrasubstituted indolin-3-ones could be easily transformed into 1H-[1,3] oxazino [3,4-a]indol-5(3H)-ones via a [4+1] cyclization process. In addition, the synthetic compound 3 s show certain antibacterial activity against S. aureus ATCC25923 and multi-drug resistance bacterial strain of S. aureus (20151027077) and its MIC values up to 8 μg/mL and 16 μg/mL, respectively. (Figure presented.).
- Zhao, Yong-Long,An, Jian-Xiong,Yang, Fen-Fen,Guan, Xiang,Fu, Xiao-Zhong,Li, Zong-Qin,Wang, Da-Peng,Zhou, Meng,Yang, Yuan-Yong,He, Bin
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p. 1277 - 1285
(2022/03/14)
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- Highly enantioselective electrosynthesis of C2-quaternary indolin-3-ones
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A highly enantioselective and direct synthesis of C2-quaternary indolin-3-ones from 2-arylindoles by combining electrochemistry and organocatalysis is described. Excellent enantioselectivities (up to 99% ee) and diastereoselectivities (>20 : 1) can be obtained through anodic oxidation in combination with asymmetric proline-catalyzed alkylation in an undivided cell under constant-current conditions.
- Chen, Yu-Jue,Chen, Yuan,Ding, Xuan,Guan, Zhi,He, Yan-Hong,Lu, Fo-Yun
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p. 623 - 626
(2020/01/28)
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- Selective synthesis of 2-indolyl-3-oxoindolines or 2-(2-aminophenyl)quinolines through Cu(II)- or Bi(III)-catalyzed tunable dimerizations of 2-alkynylanilines
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A novel and selective synthesis of 2-indolyl-3-oxoindolines or 2-(2-aminophenyl)quinolines through tunable dimerizations of 2-alkynylanilines is presented. Mechanistically, the formation of 2-indolyl-3-oxoindolines involves a Cu(OAc)2/O2-promoted intramolecular cyclization of 2-alkynylaniline to give the required indole and 3H-indol-3-one intermediates followed by the indolylation of 3H-indol-3-one. On the other hand, the formation of 2-(2-aminophenyl)quinolines is believed to go through a Bi(OTf)3/MesCO2H-catalyzed intermolecular N-nucleophilic addition between two 2-alkynylaniline molecules to give an enamine intermediate followed by its intramolecular C-nucleophilic addition/annulation. Notable features of these new methods include easily obtainable substrates, economical catalysts and oxidant, controllable selectivity, and high versatility toward diverse products.
- Jia, Ruixue,Li, Bin,Zhang, Xinying,Fan, Xuesen
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p. 6810 - 6815
(2020/09/15)
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- Synthesis of N-Fused Seven-Membered Indoline-3-ones via a Palladium-Catalyzed One-Pot Insertion Reaction from 2-Alkynyl Arylazides and Cyclic β-Diketones
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A novel strategy to synthesize N-fused seven-membered multifunctional polycyclic indoline-3-one derivatives via insertion of cyclic C-acylimines into cyclic β-diketones has been described. The reaction proceeded well under mild reaction conditions via a one-pot, three-steps method, which has shown good tolerance of various functional groups.
- Hu, Guiwen,Li, Ping,Sheng, Rong,Zhang, Xiaoxiang,Zhou, Zhiqiang
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supporting information
(2020/04/08)
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- Organocatalytic asymmetric synthesis of arylindolyl indolin-3-ones with both axial and central chirality
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An efficient method for chiral phosphoric acid-catalyzed asymmetric synthesis of arylindolyl indolin-3-ones with both axial and central chirality has been developed via the reaction of 3-arylindoles with 2-aryl-3H-indol-3-ones, and the target products were obtained in high yields with excellent enantioselectivity and diastereoselectivity.
- Fu, Hua,Peng, Fei,Wu, Xudong,Yang, Haijun,Yuan, Xi,Zhu, Changjin
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supporting information
p. 12648 - 12651
(2020/11/02)
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- Organocatalytic Asymmetric Dearomative Oxyalkylation of Indoles Enables Access to C2-Quaternary Indolin-3-ones
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A facile and efficient asymmetric dearomative oxyalkylation of indoles with TEMPO oxoammonium salt and a variety of aldehydes and ketones has been described. This metal-free approach provides a straightforward access to C2 quaternary oxindoles in high yie
- Liu, Xigong,Yan, Xue,Yu, Jin-Hai,Tang, Ying-De,Wang, Kaiming,Zhang, Hua
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supporting information
p. 5626 - 5629
(2019/08/01)
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- A straightforward TBHP-mediated synthesis of 2-amidobenzoic acids from 2-arylindoles and their antimicrobial activity
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A simple and highly efficient strategy has been developed for the synthesis of 2-amidobenzoic acids through the tert-butyl hydroperoxide (TBHP)-mediated oxygenation and sequential ring opening of 2-arylindoles in a one-pot fashion under metal-free aerobic conditions. The developed synthetic protocol is operationally simple, tolerates a wide range of functional groups, and is amenable to the gram-scale. Radical trapping experiments revealed that the reaction involves a radical pathway. The synthesized compounds (2a-s) were tested for in vitro antimicrobial activity. Among all screened compounds, 2d showed the maximum antibacterial activity against P. aerugunosa (ZOI = 17 mm, MIC = 32 μg mL-1) and compounds 2d and 2p showed the maximum (32 μg mL-1) antifungal activity against A. flavus and C. albicans.
- Patel, Om P.S.,Dhiman, Shiv,Khan, Shahid,Shinde, Vikki N.,Jaspal, Sonam,Srivathsa, Manu R.,Jha, Prabhat N.,Kumar, Anil
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supporting information
p. 5962 - 5970
(2019/06/24)
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- Chiral phosphoric acid-catalyzed direct asymmetric mannich reaction of cyclic: C -acylimines with simple ketones: Facile access to C2-quaternary indolin-3-ones
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A chiral Br?nsted acid-catalyzed direct asymmetric Mannich reaction of simple ketones with cyclic C-acylimines has been established for the synthesis of C2-quaternary indolin-3-ones. In the presence of 5-10 mol% chiral phosphoric acid, a series of 2-(2-ox
- Li, Jin-Shan,Liu, Yong-Jie,Li, Shen,Ma, Jun-An
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supporting information
p. 9151 - 9154
(2018/08/24)
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- One-Pot Synthesis of 2-Arylbenzoxazinones from 2-Arylindoles with (Diacetoxyiodo)benzene as the Sole Oxidant
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A series of synthetically interesting 2-arylbenzoxazinones was prepared from 2-arylindoles by an efficient oxidative reaction mediated by (diacetoxyiodo)benzene [PhI(OAc) 2 ] and assisted by water. PhI(OAc) 2 was used as the sole oxi
- Shang, Xian-Xing,Vu, Huu-Manh,Li, Xu-Qin
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p. 377 - 383
(2017/10/30)
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- Catalytic Asymmetric Mukaiyama-Mannich Reaction of Cyclic C-Acylimines with Difluoroenoxysilanes: Access to Difluoroalkylated Indolin-3-ones
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A catalytic enantioselective Mukaiyama-Mannich reaction of cyclic C-acylimines with difluoroenoxysilanes is reported. (S)-TRIP enables the enantioselective synthesis of a series of novel difluoroalkylated indolin-3-ones bearing a quaternary stereocenter i
- Li, Jin-Shan,Liu, Yong-Jie,Zhang, Guang-Wu,Ma, Jun-An
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supporting information
p. 6364 - 6367
(2017/12/08)
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- 2-Aryl-3H-indol-3-ones: Synthesis, electrochemical behaviour and antiplasmodial activities
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The synthesis of indolone derivatives and their antiplasmodial activity in vitro against Plasmodium falciparum at the blood stage are described. The 2-aryl-3H-indol-3-ones were synthesized via deoxygenation of indolone-N-oxides. Electrochemical behaviour, antiplasmodial activity and cytotoxicity on human tumor cell lines were compared to those of indolone-N-oxides. The antiplasmodial IC50 (concentrations at 50% inhibition) of these compounds ranged between 49 and 1327 nM. Among them, the 2-(4-dimethylaminophenyl)-5-methoxy- indol-3-one, 7, had the best antiplasmodial activity in vitro (IC50 = 49 nM; FcB1 strain) and selectivity index (SI (CC50 MCF7/IC 50 FcB1) = 423.4). Thus, the hits identified in this deoxygenated series correspond to their structural homologs in the N-oxide series with comparable electrochemical behaviour at the nitrogen-carbon double bond.
- Najahi, Ennaji,Valentin, Alexis,Fabre, Paul-Louis,Reybier, Karine,Nepveu, Fran?oise
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p. 269 - 274
(2014/04/17)
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- An asymmetric normal-electron-demand aza-Diels-Alder reaction via trienamine catalysis
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An asymmetric normal-electron-demand aza-Diels-Alder cycloaddition of 2-aryl-3H-indol-3-ones and 2,4-dienals was explored via trienamine catalysis of a chiral secondary amine. Multifunctional tricyclic polyhydropyrido[1,2-a] indoles were efficiently constructed in good stereoselectivity (up to 92% ee, >19:1 dr).
- Liu, Jing-Xin,Zhou, Qing-Qing,Deng, Jin-Gen,Chen, Ying-Chun
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p. 8175 - 8178
(2013/12/04)
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- Facile synthesis of 2-aryl-3H-indol-3-ones via singlet oxygenation of 2-arylindoles
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2-Aryl-3H-indole-3-ones have been synthesized via singlet oxygenation of 2-arylindoles in methanol followed by thermodemethoxylation of the resulting 2-aryl-2-methoxy-1,2-dihydro-3H-indol-3-ones in one pot in good yields.
- Ling
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p. 3831 - 3835
(2007/10/03)
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- Synthesis and Reactions of 2-Phenylindol-3-ones
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2-Phenyl-3-aminoindoles (2a-d) have been synthesised and converted into the corresponding 2-phenylindol-3-ones (4a-d), which on reaction with o-phenylenediamine (5a,b) and nitrostyrene give 9-substituted 5H-5a,6-dihydro-5a-phenylindoloquinoxalines
- Hiremath, Shivayogi P.,Biradar, Jaiprakash S.,Mruthyunjayaswamy, B. H. M.
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p. 308 - 310
(2007/10/02)
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