25235-85-2Relevant academic research and scientific papers
Well-Defined NNS-Mn Complex Catalyzed Selective Synthesis of C-3 Alkylated Indoles and Bisindolylmethanes Using Alcohols
Dutta, Bishal,Mondal, Avijit,Pal, Debjyoti,Sharma, Rahul,Srimani, Dipankar
supporting information, p. 3989 - 4000 (2022/03/27)
Herein, we demonstrated Mn-catalyzed selective C-3 functionalization of indoles with alcohols. The developed catalyst can also furnish bis(indolyl)methanes from the same set of substrates under slightly modified reaction conditions. Mechanistic studies reveal that the C-3 functionalization of indoles is going via a borrowing hydrogen pathway. To highlight the practical utility, a diverse range of substrates including nine structurally important drug molecules are synthesized. Furthermore, we also introduced a one-pot cascade strategy for synthesizing C-3 functionalized indoles directly from 2-aminophenyl ethanol and alcohol.
DMSO/t-BuONa/O2-Mediated Aerobic Dehydrogenation of Saturated N-Heterocycles
Cai, Hu,Tan, Wei,Xie, Yongfa,Yang, Ruchun,Yue, Shusheng
, p. 7501 - 7509 (2020/07/07)
Aromatic N-heterocycles such as quinolines, isoquinolines, and indolines are synthesized via sodium tert-butoxide-promoted oxidative dehydrogenation of the saturated heterocycles in DMSO solution. This reaction proceeds under mild reaction conditions and has a good functional group tolerance. Mechanistic studies suggest a radical pathway involving hydrogen abstraction of dimsyl radicals from the N-H bond or α-C-H of the substrates and subsequent oxidation of the nitrogen or α-aminoalkyl radicals.
Monoamine Oxidase (MAO-N) Biocatalyzed Synthesis of Indoles from Indolines Prepared via Photocatalytic Cyclization/Arylative Dearomatization
Black, Gary W.,Brancale, Andrea,Castagnolo, Daniele,Colonna, Serena,Ferla, Salvatore,Masci, Domiziana,Turner, Nicholas J.,Varricchio, Carmine,Zhao, Fei
, p. 6414 - 6421 (2020/07/09)
The biocatalytic aromatization of indolines into indole derivatives exploiting monoamine oxidase (MAO-N) enzymes is presented. Indoline substrates were prepared via photocatalytic cyclization of arylaniline precursors or via arylative dearomatization of unsubstituted indoles and in turn chemoselectively aromatized by the MAO-N D11 whole cell biocatalyst. Computational docking studies of the indoline substrates in the MAO-N D11 catalytic site allowed for the rationalization of the biocatalytic mechanism and experimental results of the biotransformation. This methodology represents an efficient example of biocatalytic synthesis of indole derivatives and offers a facile approach to access these aromatic heterocycles under mild reaction conditions.
Pd-tBuONO Cocatalyzed Aerobic Indole Synthesis
Ning, Xiao-Shan,Liang, Xin,Hu, Kang-Fei,Yao, Chuan-Zhi,Qu, Jian-Ping,Kang, Yan-Biao
, p. 1590 - 1594 (2018/04/30)
A Pd-tBuONO co-catalyzed scalable and practical synthesis of indoles with molecular oxygen as terminal oxidant is developed. Either terminal or internal 2-vinylanilines could be smoothly converted to desired indoles under one general condition. This method has been evaluated in the large scale synthesis of indomethacin and a potential anti-breast cancer drug candidate 1. (Figure presented.).
A 4 - chloro indole - 3 - acetic acid
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, (2018/04/20)
The invention discloses a 4-chloroindole-3-acetic acid preparing method. The method specifically comprises the steps of 1, conducting condensation reaction of a compound i and DMFDMA at the temperature of 80-120 DEG C in anhydrous DMF solvent, so that a compound ii is generated; 2, dissolving the compound ii in solvent formed by mixing THF with alcohol, adding Raney nickel and adding hydrazine hydrate dropwise for reaction at the temperature of 15-30 DEG C in an inert atmosphere, and obtaining a compound iii after reaction ends completely; 3, dissolving the compound iii in solvent, adding inorganic strong base and a phase transfer catalyst, adding a compound iv dropwise at the temperature of 20-35 DEG C for substitution reaction, conducting heating for backflow after the compound iv is added, and obtaining a compound v after reaction ends completely; 4, hydrolyzing the compound v to obtain the target product 4-chloroindole-3-acetic acid. According to the preparing method, no highly-toxic product is adopted as raw materials, and the whole reaction process is safe.
A indole compound and its preparation method and application (by machine translation)
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Paragraph 0131; 0136; 0137, (2018/10/02)
The invention discloses a indole compound and its preparation method and application. The indole compounds of the structural formula such as formula (I) is shown. The indoles, rice galenical demonstrate the excellent inhibitory activity, the effect of most of the compound is obviously better than the positive control drug validamycin; especially compound I - 43, I - 44, I - 54, I - 73, II - 7 and II - 17, its galenical very good living body protection and treating effect, effect is better than the positive control; more specifically, compound I - 43 of the rice sheath blight bacteriostatic activity than validamycin activity is improved by nearly 300 times. The indole compounds in the prevention and/or treatment of rice sheath blight has great application prospects. In addition the compound of the invention is simple in construction, the preparation method is simple, and is suitable for large-scale industrial production. (I). (by machine translation)
Half-sandwich structured ruthenium complex and preparation method thereof, and method for reducing o-nitrobenzene ethanol compound into indole compound
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Paragraph 0080; 0083, (2017/07/22)
The invention discloses a half-sandwich structured ruthenium complex and a preparation method thereof, and a method for reducing an o-nitrobenzene ethanol compound into an indole compound. The structure of the ruthenium complex is as shown in formula (A), wherein in the formula (A), X is halogen, R is H, -oxyl, halogen or nitro, and n is a positive integer ranging from 1 to 4. By the adoption of the preparation method, the ruthenium complex with excellent chemical stability can be obtained; meanwhile, the preparation method has the advantages of simple operation, low equipment requirement and batch production; furthermore, the ruthenium complex can be used as a catalyst for catalytically reducing the o-nitrobenzene ethanol compound (Refer to Specification).
Synthesis of indoles via dehydrogenative N-heterocyclization by supported platinum catalysts
Moromi, Sondomoyee Konika,Touchy, Abeda Sultana,Hakim Siddiki,Ali, Md. Ayub,Shimizu, Ken-Ichi
, p. 1059 - 1062 (2015/02/18)
We found the first heterogeneous Pt catalysts (Pt/Nb2O5 and Pt/HBEA) for the synthesis of indoles via acceptorless dehydrogenative cyclization of 2-(2-aminophenyl)ethanol, showing higher turnover number (TON) than previously reported catalysts. This journal is
One-pot tandem synthesis of 2,3-unsubstituted indoles, an improved Leimgruber-Batchoindole synthesis
Chen, Jinchun,Zhang, Zhikai,Liu, Sujing,Yang, Cuiyun,Xia, Chuanhai
, p. 4672 - 4675 (2014/01/17)
A concise, fast and efficient one-pot methodology has been developed for preparing 2,3-unsubstituted indoles from 2-nitrotoluenes and dimethylformamide dimethyl acetal. Compared with the classical Leimgruber-Batcho reaction, such a one-pot process simplified the operation procedures, generated less by-products and chemical residues, and resulted in higher overall yields in a shorter reaction time.
Discovery of a 4-aryloxy-1H-pyrrolo[3,2-c]pyridine and a 1-aryloxyisoquinoline series of TRPA1 antagonists
Hu, Yun-Jin,St.-Onge, Miguel,Laliberté, Sébastien,Vallée, Frédéric,Jin, Shujuan,Bedard, Leanne,Labrecque, Jean,Albert, Jeffrey S.
supporting information, p. 3199 - 3203 (2015/02/19)
A series of TRPA1 antagonists is described having a 4-aryloxy-1H-pyrrolo[3,2-c]pyridine or a 1-aryloxyisoquinoline scaffold. These compounds have high ligand efficiency and favorable physical properties and may thus serve as scaffolds for further optimization.
