56366-45-1Relevant academic research and scientific papers
An electrochemical synthesized by catalytic oxidation of 3 - mercapto indole compounds
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Paragraph 0025-0056, (2019/05/16)
The invention discloses a synthesizing method for a 3-mercapto indole compound through electrochemical catalytic oxidation. According to the method, a three-electrode system is used, a cathode and ananode are graphite electrodes, and a silver nitrate acetonitrile solution of 0.1mol/L is used as a reference electrode; and the indole compounds, disulfide and potassium iodide are added in a sodium tetrafluoroborate acetonitrile solution, stirring and electrolytic reaction are conducted for 3-24h under the condition of the temperature of 45-75 DEG C and 0.2-0.6 V constant voltage, a reaction solution is post-processed, and the product 3-mercapto indole compound is obtained. By means of the synthesizing method, operation is simple, convenient and safe, the yield of the product 3-mercapto indole compound is high, the reaction condition is mild, clean electrical energy is used as a redox agent, and the environmental cost is greatly reduced.
Fe(III)-Catalyzed direct C3 chalcogenylation of indole: The effect of iodide ions
Luz, Eduardo Q.,Seckler, Diego,Araújo, Janylson Souza,Angst, Leonardo,Lima, David B.,Maluf Rios, Elise Ane,Ribeiro, Ronny R.,Rampon, Daniel S.
supporting information, p. 1258 - 1266 (2019/02/03)
A mild and efficient iron (III)-catalyzed C3 chalcogenylation of indoles has been developed and the role of the iodide ions in this transformation was investigated. EPR experiments revealed the reduction of Fe(III) to Fe(II) under the reaction conditions, supporting the formation of molecular iodine in the system, which in effect catalyze the reaction. The scope of the chalcogenylation was broad and the synthesis of more functionalized 3-selenylindoles was explored.
NH4I/1,10-phenanthroline catalyzed direct sulfenylation of N-heteroarenes with ethyl arylsulfinates
Chen, Lingjuan,Zhang, Jun,Wei, Yueting,Yang, Zhen,Liu, Ping,Zhang, Jie,Dai, Bin
, (2019/10/14)
An efficient synthesis of N-heterocyclic aryl sulfides via NH4I/1,10-phenanthroline-catalyzed direct sulfenylation reactions was reported. In this reaction, heteroarenes such as indoles, and pyrroles serve as nucleophiles by installing a arylthio group at the C3 and C2 position of heterocycles, respectively. With readily accessible and free of unpleasant odor ethyl arylsulfinates as sulfur reagents, the metal-free-catalyzed direct sulfenylation of N-heteroarenes has been developed. 3-Arylthio-indoles and 2-arylthio-pyrroles derivatives were obtained in moderate to excellent yields, even on gram scale. The reaction was general for a broad scope of substrates and demonstrated good tolerance to a variety of functional groups.
Mechanistic and experimental study on copper-catalyzed C3-sulfenylation of indoles with sulfur powder and aryl iodides
Ge, Xin,Cheng, Lin,Sun, Fengli,Liu, Xuemin,Chen, Xinzhi,Qian, Chao,Zhou, Shaodong
, p. 32 - 37 (2019/02/19)
The copper-catalyzed sulfenylation of indoles with aryl iodide and sulfur powder has been investigated both experimentally and theoretically. This protocol provides a direct and facile approach to prepare 3-sulfenylindoles with moderate to excellent yields and good functional-group tolerance. The in-situ IR analysis provided evidence for that NaOAc could promote the synthesis of diphenyl disulfide by the coupling of aryl iodide and sulfur powder. According to DFT calculations, the coupling pathway involving the intermediate N-methyl-3-iodoindole is more favored than the direct coupling by the C–H activation of indole. The N-methyl-3-iodoindole was identified as a crucial intermediate in the catalytic cycle.
Synergistic Dual Role of [hmim]Br-ArSO2Cl in Cascade Sulfenylation-Halogenation of Indole: Mechanistic Insight into Regioselective C-S and C-S/C-X (X = Cl and Br) Bond Formation in One Pot
Equbal, Danish,Singh, Richa,Saima,Lavekar, Aditya G.,Sinha, Arun K.
, p. 2660 - 2675 (2019/03/14)
Bifunctionalized indoles are an important class of biologically active heterocyclic compounds and potential drug candidates. Because of the lack of efficient synthetic methods, one pot cascade synthesis of these compounds is rare and remains a challenge.
Metal Free Mono- and 2,3-Bis-sulfenylation of Indoles in Water with Sodium Sulfinates as a Sulfur Source
Liu, Changqing,Fan, Jian,Wu, Manyi,Chen, Jiahui,Zhao, Yiming,Xie, Meihua
, p. 819 - 825 (2018/07/30)
An iodine-PPh3 mediated sulfenylation of indoles in water with stable and odorless sodium sulfinates as the sulfur source is described. The reaction could afford monosulfenylated indoles in moderate to excellent yields under metal free conditions. Moreover, double C—H sulfenylation of indoles at 2- and 3-positions has also been achieved by using excess sodium sulfinates under the optimized reaction conditions.
Electrochemical sulfenylation of indoles with disulfides mediated by potassium iodide
Chen, Chen,Niu, Pengfei,Shen, Zhenlu,Li, Meichao
, p. G67 - G74 (2018/05/22)
A novel electrochemical system for sulfenylation of indoles with disulfides to generate 3-sulfenylindoles via C-S bond formation mediated by potassium iodide at a low potential was developed. Iodine was electrogenerated from iodide ions at a graphite anode and showed a high catalytic activity for the electrochemical sulfenylation reactions. A variety of aromatic, heteroaromatic and aliphatic disulfides could react with 2-methlyindole to synthesize the corresponding 3-sulfenylindoles in good to excellent yields. In addition, protected and unprotected indoles with various groups, especially electron-donating groups, also performed well in the sulfenylation reactions. The transformation, which proceeded through the redox of iodine and the generation of intermediate 3-iodoindole, provided an efficient and environmentally benign protocol for the synthesis of 3-sulfenylindoles under mild conditions.
An efficient: T -BuOK promoted C3-chalcogenylation of indoles with dichalcogenides
Yu, Yuanzu,Zhou, Yan,Song, Zengqiang,Liang, Guang
supporting information, p. 4958 - 4962 (2018/07/25)
A versatile and efficient method for the synthesis of 3-chalcogenyl-indoles from indoles and dichalcogenides employing t-BuOK as a promoter at room temperature has been achieved. The present protocol exhibited a broad functional group tolerance. Diverse 3-sulfenyl- and 3-selenyl-indoles were rapidly obtained in good to excellent yields with high regioselectivities. It is noteworthy that this transformation was applicable to N-protected and N-unprotected indoles, allowing N-deprotection and C3-chalcogenylation of indoles in one step.
Preparation method of 3-thioether indole or 3-selenide indole
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Paragraph 0054-0056, (2018/10/19)
The invention discloses a preparation method of 3-thioether indole or 3-selenide indole. The method comprises the following steps that 3-thioether indole and 3-selenide indole are synthesized by usingpotassium tert-butoxide as alkali and using an indole type compound, disulfide ether and diselenide ether as substrates in an DMF solvent. The preparation method has the advantages that the reactionraw materials are cheap and can be easily obtained; the preparation method is simple; the potassium tert-butoxide is used as alkali; reaction is performed at room temperature; the reaction time is short; the yield is high; the operation is simple; the preparation method is applicable to the synthesis of two compounds of 3-thioether indole and 3-selenide indole. The method can be used for synthetizing a series of 3-thioether indole and 3-selenide indole; the synthetized product is an active compound.
Direct, Metal-free C(sp2)?H Chalcogenation of Indoles and Imidazopyridines with Dichalcogenides Catalysed by KIO3
Rafique, Jamal,Saba, Sumbal,Franco, Marcelo S.,Bettanin, Luana,Schneider, Alex R.,Silva, Lais T.,Braga, Antonio L.
supporting information, p. 4173 - 4180 (2018/02/06)
Herein, we report a greener protocol for the synthesis of 3-Se/S-indoles and imidazo[1,2-a]pyridines through direct C(sp2)?H bond chalcogenation of heteroarenes with half molar equivalents of different dichalcogenides, using KIO3 as a non-toxic, easy-to-handle catalyst and a stoichiometric amount of glycerol. The reaction features are high yields, based on atom economy, easy performance on gram-scale, metal- and solvent-free conditions as well as applicability to different types of N-heteroarenes.
