35856-00-9Relevant academic research and scientific papers
Facile and effective synthesis of spirocycloalkanones
Zoidis, Grigoris,Kolocouris, Nicolas
, p. 531 - 535 (2011)
Spiroadamantane cyclopentanone and cyclohexanone have been prepared by a simple and effective method, including the synthesis of the key intermediate dinitriles and their intramolecular Thorpe-Ziegler cyclization. In this method, the key step of the dinitriles formation was accomplished by a novel base-induced allylation protocol which involved the treatment of 2-adamantanecarbonitrile precursor with lithium diisopropylamine and allylbromide. Moreover, the cyclization methodology used, allowed to obtain the respective cyanoenamine in high yields, when the respective dinitriles were treated with the previous base. Acidic hydrolysis of enamines led to the desired cycloalkanones, which constitute versatile intermediates in the synthesis of spiroadamantanamines and other bioactive molecules concerning our pharmacological studies.
Direct C(sp3)-H Cyanation Enabled by a Highly Active Decatungstate Photocatalyst
Kim, Kunsoon,Lee, Seulchan,Hong, Soon Hyeok
supporting information, p. 5501 - 5505 (2021/07/26)
A highly efficient, direct C(sp3)-H cyanation was developed under mild photocatalytic conditions. The method enabled the direct cyanation of various C(sp3)-H substrates with excellent functional group tolerance. Notably, complex natural products and bioactive compounds were efficiently cyanated.
Preparation method of alkyl nitrile compound
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Paragraph 0189-0191; 0204-0206, (2020/05/14)
The invention discloses a preparation method of an alkyl nitrile compound shown as formula I. The preparation method comprises the following step: in a solvent, in the presence of an additive and a catalyst, Zn (CN) 2 and an alkyl halide shown as formula II are subjected to a coupling reaction as shown in the specification to obtain the alkyl nitrile compound as shown in the formula I, wherein theadditive comprises an alkali, the catalyst comprises a nickel compound and a phosphine ligand; the nickel compound is one or more of zero-valent nickel, monovalent nickel salt and divalent nickel salt; when the nickel compound contains zero-valent nickel or divalent nickel salt, the catalyst further comprises a reducing agent. According to the preparation method disclosed by the invention, cyanation of an alkyl halide can be simply, conveniently and efficiently realized by using a cheap catalytic system, and the preparation method also has good functional group compatibility and substrate universality.
INTRAESOPHAGEAL ADMINISTRATION OF TARGETED NITROXIDE AGENTS FOR PROTECTION AGAINST IONIZING IRRADIATION-INDUCED ESOPHAGITIS
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Paragraph 0152; 0163, (2019/07/23)
Provided herein are compositions and related methods useful for prevention or mitigation of ionizing radiation-induced esophagitis. The compositions comprise compounds comprising a nitroxide-containing group attached to a mitochondria-targeting group. The
Nickel-Catalyzed Decarbonylative Cyanation of Acyl Chlorides
Wang, Zhenhua,Wang, Xiu,Ura, Yasuyuki,Nishihara, Yasushi
supporting information, p. 6779 - 6784 (2019/08/26)
Ni-catalyzed decarbonylative cyanation of acyl chlorides with trimethylsilyl cyanide has been achieved. This transformation is applicable to the synthesis of an array of nitrile compounds bearing a wide range of functional groups under neutral conditions. The step-by-step experimental studies revealed that the reaction sequences of the present catalytic reaction are oxidative addition, transmetalation, decarbonylation, and reductive elimination.
Ring-fused compound, pharmaceutical composition containing same and application of compound
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Paragraph 0256-0258, (2018/04/01)
The invention discloses a ring-fused compound, a preparation method thereof, pharmaceutical composition containing the compound and an application of the compound. A polycyclic compound (I) as well asan isomer, a prodrug, a stable isotopic derivative or pharmacologically acceptable salt of the compound (I) has the following structure. The polycyclic compound has good IDO1 and/or TDO2 inhibition functions, can effectively treat, relieve and/or prevent various diseases which are related with IDO1 and/or TDO2, such as cancer, virus infection, autoimmune diseases or the like.
Synthesis of Nitriles from Primary Amides or Aldoximes under Conditions of a Catalytic Swern Oxidation
Ding, Rui,Liu, Yongguo,Han, Mengru,Jiao, Wenyi,Li, Jiaqi,Tian, Hongyu,Sun, Baoguo
, p. 12939 - 12944 (2018/10/20)
The preparation of nitriles from primary amides or aldoximes was achieved by using oxalyl chloride with a catalytic amount of dimethyl sulfoxide in the presence of Et3N. The reactions were complete within 1 h after addition at room temperature. A diverse range of cyano compounds were obtained in good to excellent yields, including aromatic, heteroaromatic, cyclic, and acyclic aliphatic species.
C H Bond Arylation of Diamondoids Catalyzed by Palladium(II) Acetate
Larrosa, Marta,Heiles, Sven,Becker, Jonathan,Spengler, Bernhard,Hrdina, Radim
supporting information, p. 2163 - 2171 (2016/07/16)
We have developed an effective approach to 1,2-disubstituted diamondoids by palladium(II) acetate catalyzed functionalization of C H bond. Selective mono-arylation of the adamantane framework was achieved using picolylamide as a directing group in yields up to 87 %. Kinetic studies in combination with deuterium labeling experiments, competitive experiments and mass spectrometry contribute to the mechanistic understanding of the arylation process of alkanes with number of C H bonds neighboring the directing group. Triflic anhydride promoted cyclization of the directing group generates imidazo[1,5-a]pyridine derivatives. Acid-mediated removal of the directing group provides access to 2-aryl diamondoid carboxylic acids, which are common precursors for the synthesis of various bioactive compounds (drug candidates). (Figure presented.) .
FUSED-RING COMPOUNDS, PHARMACEUTICAL COMPOSITION AND USES THEREOF
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Paragraph 296; 297; 298, (2016/09/15)
This disclosure is related to a fused-ring compound of formula (I) and/or a pharmaceutically acceptable salt thereof, a pharmaceutical composition comprising the fused ring compound of formula (I) and/or a pharmaceutically acceptable salt thereof, preparation methods thereof, and use thereof in modulating activity of indoleamine 2, 3-dioxygenase (IDO) and/or tryptophan 2, 3-dioxygenase (TDO). This disclosure further provides methods of treating IDO and/or TDO-associated diseases, including cancer, viral infection and autoimmune diseases.
2-Substituted and 2,2-disubstituted adamantane derivatives as models for studying substituent chemical shifts and C-Hax?Yax cyclohexane contacts - results from experimental and theoretical NMR spectroscopic chemical shifts and DFT structures
Kolocouris, Antonios,Koch, Andreas,Kleinpeter, Erich,Stylianakis, Ioannis
supporting information, p. 2463 - 2481 (2015/03/30)
Abstract The complete 1H and 13C NMR chemical shifts assignment for various 2-substituted and 2,2-disubstituted adamantane derivatives 1-38 in CDCl3 solution was realized on the basis of NMR experiments combined with chemical structure information and DFT-GIAO (B3LYP/6-31+G(d,p)-GIAO) calculations of chemical shifts in solution. Substituent-induced 13C NMR chemical shifts (SCS) are discussed. C-Hax?Yax contacts are a textbook prototype of steric hindrance in organic chemistry. The nature of these contacts will be further investigated in this work on basis of new adamantane derivatives, which are substituted at C-2 to provide models for 1,4-C-Hax?Yax and 1,5-C-Hax?Yax contacts. The B3LYP/6-31+G(d,p) calculations predicted the presence of NBO hyperconjugative attractive interactions between C-Hax and Yax groups along C-Hax?Yax contacts. The 1H NMR signal separation, Δδ(γ-CH2), reflects the strength of the H-bonded C-Haxa?Yax contact.
