526-55-6Relevant academic research and scientific papers
SUBSTITUTED TETRAHYDROPYRANOINDOLES, DERIVATIVES THEREOF, AND THEIR METHODS OF SYNTHESIS AND USE
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Paragraph 0152; 0153; 0197, (2021/01/25)
Disclosed herein are tetrahydropyranoindole compounds and derivatives thereof, as well as their methods of synthesis and use. The disclosed compounds may be synthesized by methods that utilize a cooperative hydrogen bond donor/Br?nsted acid system. The disclosed compounds may be useful for treating a disease, disorder, or a symptom thereof in a subject in need thereof, such as pain, swelling, and joint stiffness. The disclosed compounds also may be useful for treating cell proliferative diseases and disorders such as cancer.
S -indole benzamide derivative as well as preparation method and application thereof
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Paragraph 0030; 0034-0036, (2021/09/15)
S - Indole benzamide derivatives as well as a preparation method and application thereof relate to the technical field of pharmacy. The derivative has a structural formula. The specific preparation method comprises the following steps: taking indole as a starting raw material and performing acylation reaction. Reaction, oxidation reaction, (R)- (+) -tert-butylsulfenamide asymmetric synthesis reaction, hydrolysis reaction and acylation reaction to give the target product. By means of the method, a novel antiviral drug with a development prospect can be obtained, and the yield is high.
AZEPINO-INDOLES AND OTHER HETEROCYCLES FOR TREATING BRAIN DISORDERS
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Paragraph 0203, (2020/09/12)
The present invention provides azepino-indoles and other heterocycles and methods of using the compounds for treating brain disorders.
Improved and Flexible Synthetic Access to the Spiroindole Backbone of Cebranopadol
Christoffers, Jens,Schmidtmann, Marc,Wachtendorf, Daniel
supporting information, p. 6420 - 6423 (2020/09/02)
By changing the dimethylamino to a nitro group, a novel synthetic access to the spirocyclic opioid analgesic cebranopadol was developed that is much more efficient compared with the established route. On the basis of the α-acidity of α-nitrotoluene, the two-fold Michael addition to acrylate gave an acyclic precursor compound, which was easily transformed by Dieckmann condensation and decarboxylation to the cyclohexanone derivative needed for the annulation of the indole ring by an oxa-Pictet-Spengler reaction. As an additional benefit, the reduction of the nitro group furnished an amine, which could be late-stage-diversified to carboxamides, sulfonamides, ureas, and N-alkyl congeners. The transformation of the nitro group at the spirocyclic scaffold to the dimethylamino function of the actual title compound was achieved in one step with zinc/formic acid/formaldehyde in 83% yield.
Synthesis of chiral [2,3]-fused indolines through enantioselective dearomatization inverse-electron-demand Diels-Alder reaction/oxidation of indoles with 2-(2-nitrovinyl)-1,4-benzoquinone
Cheng, Shaobing,Liu, Hui,Liu, Min,Yuan, Weicheng,Zhang, Jiayan,Zhang, Xiaomei,Zhao, Sihan
supporting information, p. 4200 - 4203 (2020/04/22)
Enantioselective dearomatization inverse-electron-demand Diels-Alder reaction/oxidation of indoles with 2-(2-nitrovinyl)-1,4-benzoquinone was realised using a chiral bisoxazoline/zinc complex as a catalyst. This transformation allowed for the synthesis of enantioenriched six-membered [2,3]-fused indolines (up to 99% yield and 88% ee).
Tandem Olefin Isomerization/Cyclization Catalyzed by Complex Nickel Hydride and Br?nsted Acid
Kathe, Prasad M.,Caciuleanu, Alexandru,Berkefeld, Andreas,Fleischer, Ivana
, p. 15183 - 15196 (2020/11/30)
We disclose a nickel/Br?nsted acid-catalyzed tandem process consisting of double bond isomerization of allyl ethers and amines and subsequent intramolecular reaction with nucleophiles. The process is accomplished by [(Me3P)4NiH]N(SO2CF3)2 in the presence of triflic acid. The methodology provides rapid access to tetrahydropyran-fused indoles and other oxacyclic scaffolds under very low catalyst loadings.
Aerobic Dehydrogenation of N-Heterocycles with Grubbs Catalyst: Its Application to Assisted-Tandem Catalysis to Construct N-Containing Fused Heteroarenes
Kawauchi, Daichi,Noda, Kenta,Komatsu, Yoshiyuki,Yoshida, Kei,Ueda, Hirofumi,Tokuyama, Hidetoshi
supporting information, p. 15793 - 15798 (2020/10/12)
An aerobic dehydrogenation of nitrogen-containing heterocycles catalyzed by Grubbs catalyst is developed. The reaction is applicable to various nitrogen-containing heterocycles. The exceptionally high functional group compatibility of this method was confirmed by the oxidation of an unprotected dihydroindolactam V to indolactam V. Furthermore, by taking advantage of the oxygen-mediated structural change of the Grubbs catalyst, we integrated ring-closing metathesis and subsequent aerobic dehydrogenation to develop the novel assisted-tandem catalysis using molecular oxygen as a chemical trigger. The utility of the assisted-tandem catalysis was demonstrated by the concise synthesis of N-containing fused heteroarenes including a natural antibiotic, pyocyanine.
A is by aromatic carboxylic acid non-catalytic reaction of alcohol compound (by machine translation)
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Paragraph 0030, (2019/04/17)
The present invention discloses a non-catalytic reaction of the aromatic carboxylic acid preparation of alcohol compound. In an inert gas atmosphere, after dehydration and deoxidation treatment of the reaction bottle [...] borane and carboxylic acid stirring and mixing, reaction 6 - 12 hours to obtain borate, further hydrolyzed into alcohol; said carboxylic acid is benzoic acid, 4 - bromobenzoic acid, 4 - fluoro benzoic acid, 1 - naphthoic acid, 2 - methoxybenzene formic acid and the like. The invention for the first time in the absence of catalyst under the conditions of high-efficiently using carboxylic acid with borane generating borohydrite reaction, carbonyl compound with borane generating borohydrite reaction preparation borate, further hydrolysis alcohol, provides new programme. (by machine translation)
Iron-Catalyzed β-Alkylation of Alcohols
Bettoni, Leó,Gaillard, Sylvain,Renaud, Jean-Luc
supporting information, p. 8404 - 8408 (2019/10/16)
β-Branched alkylated alcohols have been prepared in good yields using a double-hydrogen autotransfer strategy in the presence of our diaminocyclopentadienone iron tricarbonyl complex Fe1. The alkylation of some 2-arylethanol derivatives was successfully addressed with benzylic alcohols and methanol as alkylating reagents under mild conditions. Deuterium labeling experiments suggested that both alcohols (2-arylethanol and either methanol or benzyl alcohol) served as hydrogen donors in this cascade process.
Method for preparing alcoholic compound from anilino lithium compound as catalyst
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, (2019/03/06)
The invention relates to an application of an anilino lithium compound, in particular to a method for preparing an alcoholic compound from the anilino lithium compound as a catalyst. The catalyst, borane and carboxylic acid are stirred and mixed uniformly, subjected to a reaction and exposed to air to terminate the reaction, a reacted liquid is subjected to reduced-pressure treatment for solvent removal, silica gel and methanol are added, and the alcoholic compound is obtained by hydrolysis. The anilino lithium compound can perform high-activity catalysis on the reaction between carboxylic acid and borane at room temperature, dose of the catalyst is only 0.8mol% of the mole ratio of carboxylic acid, compared with the conventional catalysis system, the commercial reagent anilino lithium compound is used, reaction conditions are mild, and yield of borate with different substituents under limit conditions can reach 90% or higher.
