3161-51-1Relevant academic research and scientific papers
Manganese-Catalyzed Anti-Markovnikov Hydroamination of Allyl Alcohols via Hydrogen-Borrowing Catalysis
Das, Kuhali,Sarkar, Koushik,Maji, Biplab
, p. 7060 - 7069 (2021/06/30)
Controlling the selectivity in a hydroamination reaction is an extremely challenging yet highly desirable task for the diversification of amines. In this article, a selective formal anti-Markovnikov hydroamination of allyl alcohols is presented. It enables the versatile synthesis of valuable γ-amino alcohol building blocks. A phosphine-free Earth's abundant manganese(I) complex catalyzed the reaction under hydrogen-borrowing conditions. A vast range of aliphatic, aromatic amines, drug molecules, and natural product derivatives underwent successful hydroamination with primary and secondary allylic alcohols with excellent functional group tolerance (57 examples). The catalysis could be performed on a gram scale and has been applied for the synthesis of drug molecules. The mechanistic studies revealed the metal-ligand bifunctionality as well as hemilability of the ligand backbone as the key design principle for the success of this catalysis.
NEW MACROCYCLIC LRRK2 KINASE INHIBITORS
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Page/Page column 80; 82-83, (2021/11/13)
Compounds of formula (I): wherein R, X1, X2, X3, Z1, Z2, Z3, A and Ra are as defined in the description. Medicaments.
Niraparib intermediate, preparation method and application thereof, and synthesis method of niraparib
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Paragraph 0064; 0066-0067; 0093; 0095-0096, (2020/09/08)
The invention relates to a compound alpha-(3-aminopropyl)-p-bromophenylacetic acid, a preparation method and application thereof, (S)-3-(4-bromophenyl)-piperidine-2-one, a preparation method and application thereof, and synthesis methods of (S)-3-(4-bromophenyl)-piperidine) p-toluenesulfonate, N-Boc-(3S)-(4-bromophenyl)piperidine and niraparib. 4-bromophenylacetate 5 is used as a raw material, a nucleophilic reaction is carried out on the raw material and a nitrogen source reagent 4 under the action of an alkali to generate a compound 6; the compound 6 is subjected to deprotection and hydrolysis to obtain an amino acid compound 7; and the amino acid compound 7 is subjected to chiral column separation or chemical resolution to obtain compounds 8 and 9; and the separated enantiomer 8 can besubjected to racemization and resolution conversion (or chiral column separation) to obtain a compound 9, and the process material cost is greatly reduced. After the compound 9 is obtained, a compound1 can be obtained through conventional condensation reaction ring closing, reduction and BOC loading. Splitting operation is advanced, and the enantiomer 8 is subjected to racemization recovery treatment and is repeatedly applied to different splitting batches to continuously obtain the product 9, so the process material cost is lower.
Iron-Catalyzed Anti-Markovnikov Hydroamination and Hydroamidation of Allylic Alcohols
Ma, Wei,Zhang, Xiaohui,Fan, Juan,Liu, Yuxuan,Tang, Weijun,Xue, Dong,Li, Chaoqun,Xiao, Jianliang,Wang, Chao
supporting information, p. 13506 - 13515 (2019/09/09)
Hydroamination allows for the direct access to synthetically important amines. Controlling the selectivity of the reaction with efficient, widely applicable, and economic catalysts remains challenging, however. This paper reports an iron-catalyzed formal anti-Markovnikov hydroamination and hydroamidation of allylic alcohols, which yields γ-amino and γ-amido alcohols, respectively. Homoallylic alcohol is also feasible. The catalytic system, consisting of a pincer Fe-PNP complex (1-4 mol %), a weak base, and a nonpolar solvent, features exclusive anti-Markovnikov selectivity, broad substrate scope (>70 examples), and good functional group tolerance. The reaction could be performed at gram scale and applied to the synthesis of drug molecules and heterocyclic compounds. When chiral substrates are used, the stereochemistry and enantiomeric excess are retained. Further application of the chemistry is seen in the functionalization of amino acids, natural products, and existing drugs. Mechanistic studies suggest that the reaction proceeds via two cooperating catalytic cycles, with the iron complex catalyzing a dehydrogenation/hydrogenation process while the amine substrate acts as an organocatalyst for the Michael addition step.
Synthesis and antikinetoplastid evaluation of bis(benzyl)spermidine derivatives
Jagu, Elodie,Pomel, Sébastien,Diez-Martinez, Alba,Rascol, Estelle,Pethe, Stéphanie,Loiseau, Philippe M.,Labruère, Rapha?l
, p. 655 - 666 (2018/03/23)
This study describes the synthesis and the biological evaluation of twenty-four original bis(benzyl)spermidines. Structural modifications of the polyamine scaffold were performed in order to avoid easily metabolized bonds. Some bis(benzyl)polyamine derivatives have demonstrated promising activity in vitro against Trypanosoma brucei gambiense and Leishmania donovani. From the enzymatic experiments on trypanothione reductase, we observed that this enzyme was not targeted by our compounds. In vivo evaluation on Swiss mice model infected by T. b. gambiense or L. donovani was done with the most interesting compound of the series.
New N,N-dimethylcarbamate inhibitors of acetylcholinesterase: design synthesis and biological evaluation
De Vita, Daniela,Pandolfi, Fabiana,Ornano, Luigi,Feroci, Marta,Chiarotto, Isabella,Sileno, Ilaria,Pepi, Federico,Costi, Roberta,Di Santo, Roberto,Scipione, Luigi
, p. 106 - 113 (2016/12/22)
A series of N,N-dimethylcarbamates containing a N,N-dibenzylamino moiety was synthesized and tested to evaluate their ability to inhibit Acetylcholinesterase (AChE). The most active compounds 4 and 8, showed 85 and 69% of inhibition at 50 μM, respectively
Stereoselective synthesis and conformational analysis of unnatural tetrapeptides. Part 2
Almiento, Giosue M.,Balducci, Daniele,Bottoni, Andrea,Calvaresi, Matteo,Porzi, Gianni
, p. 2695 - 2711 (2008/09/17)
Stereoselective synthesis of unnatural tetrapeptides 20a and 20b, 21a and 21b and 30 and 31, containing two l-valine units and two unnatural α-amino acids (ornithine and modified aspartic acid), has been accomplished starting from the l-valine derived chiral synthon 1. Structural investigations of these non-proteinogenic peptides have been carried out on the acetamido derivatives using 1H NMR, IR spectroscopic techniques and a conformational analysis based on molecular dynamics (MD) and cluster analysis.
Diesters of carbonic acid endowed with antiviral and anti-inflammatory activity
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, (2008/06/13)
Diesters of carbonic acid disubstituted with primary, secondary or tertiary amine groups, pharmaceutically acceptable salts thereof, and their use as antiviral and inti-inflammatory agents.
Ytterbium Triflate and High Pressure-mediated Ring Opening of Epoxides with Amines
Meguro, Masaki,Asao, Naoki,Yamamoto, Yoshinori
, p. 2597 - 2602 (2007/10/02)
Ring opening of epoxides with amines in THF takes place very readily in the presence of catalytic amounts of ytterbium triflate to give the corresponding β-amino alcohols in good to high yields.With tri- and tetra-substituted epoxides, the use of an excess (2 - 3 equiv.) of the amine is needed.The Yb(OTf)3-catalysed reaction of epoxides with amines in CH2Cl2 is quite complex; the yield of amino alcohols is generally lower and depends upon the addition order of the catalyst, amine and epoxide.The ring opening is accomplished also under high pressures in the absence of Yb(OTf)3.Ring opening with a combination of Yb(OTf)3 in CH2Cl2 and high pressure is more effective than the use, independently, of either Yb(OTf)3 or the high-pressure method.Oxetanes and β-lactones undergo ring opening in the presence of Yb(OTf)3.
Regioselective Reductive Ring Cleavage of 3-Benzyltetrahydro-1,3-oxazines to 3-Dialkylaminopropanols and of 3-Benzyl-3-methyltetrahydro-1,3-oxazinium Iodides to Alkyl 3-Dialkylaminopropyl Ethers
Alberola, Angel,Alvarez, M. Angeles,Andres, Celia,Gonzalez, Alfonso,Pedrosa, Rafael
, p. 153 - 156 (2007/10/02)
3-Benzyltetrahydro-1,3-oxazines and their methiodides are ring-cleaved upon reduction with lithium aluminum hydride to give 3-dialkylaminopropanols or alkyl 3-dialkylaminopropyl ethers, respectively, in good yields.The reducing agent regioselectively clea
