20919-36-2Relevant academic research and scientific papers
Synthesis and luminescence properties of 2-(benzylcarbamoyl)phenyl derivatives and their europium complexes
Guo, Dongcai,He, Wei,Liu, Bang,Gou, Lining,Li, Ruixia
, p. 280 - 286 (2013)
Six novel 2-(benzylcarbamoyl)phenyl derivatives were synthesized and characterized by 1H-NMR, mass spectrometry, infrared spectra and elemental analysis. Their europium complexes were prepared and characterized by elemental analysis, EDTA titri
Synthesis of functionalized benzo[1,3]dioxin-4-ones from salicylic acid and acetylenic esters and their direct amidation
Babu, Beneesh P.,Bhaskaran, Rasmi P.,Nayak, Kalinga H.
, p. 24570 - 24574 (2021)
Direct synthesis of 4H-benzo[d][1,3]dioxin-4-one derivatives from salicylic acids and acetylenic esters (both mono- and disubstituted) has been described. The reaction is mediated by CuI and NaHCO3in acetonitrile. Room temperature amidation of
Graphene oxide: A convenient metal-free carbocatalyst for facilitating amidation of esters with amines
Patel, Khushbu P.,Gayakwad, Eknath M.,Shankarling, Ganapati S.
, p. 2661 - 2668 (2020/02/20)
Herein, we report a graphene oxide (GO) catalyzed condensation of non-activated esters and amines, that can enable diverse amides to be synthesized from abundant ethyl esters forming only volatile alcohol as a by-product. GO accelerates ester to amide conversion in the absence of any additives, unlike other catalysts. A wide range of ester and amine substrates are screened to yield the respective amides in good to excellent yields. The improved catalytic activity can be ascribed to the oxygenated functionalities present on the graphene oxide surface which forms H-bonding with the reactants accelerating the reaction. Improved yields and a wide range of functional group tolerance are some of the important features of the developed protocol.
Dioxomolybdenum(VI) Complexes with Salicylamide Ligands: Synthesis, Structure, and Catalysis in the Epoxidation of Olefins under Eco-Friendly Conditions
Annese, Cosimo,Caputo, Daniela,D'Accolti, Lucia,Fusco, Caterina,Nacci, Angelo,Rossin, Andrea,Tuci, Giulia,Giambastiani, Giuliano
supporting information, p. 221 - 229 (2019/01/04)
Five salicylamides [R1R2SaAmH; R1, R2 = N-substituents: nBu, H (1a); tBu, H (1b); nOc, H (1c); Bn, H (1d); and nBu, nBu (1e)] were successfully coordinated to the dioxomolybdic fragment, resulting in MoO2(R1R2SaAm)2 complexes 2a-e, which were characterized through elemental analysis, IR, 1H- and 13C NMR, ESI-HRMS, and XRD (for 2a,b,e). All complexes are active catalysts in the solvent-free epoxidation of cis-cyclooctene with tert-butyl hydroperoxide in decane (TBHPdec), showing high turnover frequencies (TOF 1890 h–1 for 2b) at 1 % loading. Using aqueous TBHP (TBHPaq) or H2O2, selectivity to cyclooctene oxide is always 100 %, although reactions are more sluggish. The 2c/TBHPaq system, which displays the best TOF (1070 h–1) at 0.25 % loading and 75 °C, allowed for the quantitative conversion of trans-2-octene into its epoxide, while low epoxide selectivity was observed in the case of 1-octene, styrene, and methyl oleate. In the latter case, 90 % epoxide selectivity at 92 % conversion was achieved with the 2b/TBHPdec system at 55 °C, under solvent-free conditions. Compared to related MoO2X2(O-amide)-type complexes, 2a-e exhibit increased catalytic performance under the greener conditions involving the use of aqueous oxidants.
IDO inhibitors
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Page/Page column 317, (2018/09/02)
Presently provided are methods for (a) modulating an activity of indoleamine 2,3-dioxygenase comprising contacting an indoleamine 2,3-dioxygenase with a modulation effective amount of a compound as described in one of the aspects described herein; (b) treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression in a subject in need thereof, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (c) treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (d) enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent and a compound as described in one of the aspects described herein; (e) treating tumor-specific immunosuppression associated with cancer comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; and (f) treating immunosuppression associated with an infectious disease, e.g., HIV-I infection, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount a compound as described in one of the aspects described herein.
Fast synthesis of amides from ethyl salicylate under microwave radiation in a solvent-free system
Lima, Rafaely N.,Silva, Valdenizia R.,De Santos, Luciano,Bezerra, Daniel P.,Soares, Milena B. P.,Porto, André L. M.
, p. 56566 - 56574 (2017/12/26)
In this study, amide bond formation, one of the most important reactions in organic chemistry, it was evaluated using ethyl salicylate and ten different primary amines. Under the optimized experimental conditions, i.e. 60 °C, hexane, phenylboronic acid-PBA (15 mol%), boric acid-BA (15 mol%) or without catalyst-WC, using a hot-plate for 24 h, amides were obtained in excellent isolated yields (WC, 77-94% to S-Aa-Ad; PBA, 11-94% to S-Ae-Aj; and BA, 28-90% to S-Ae-Aj). The reaction employing CAL-B also permitted a moderate conversion for the production of amides S-Ae-Aj (3-42%). However, in our efforts to reduce the amide synthesis time (24 h), the reactions were performed in the presence of microwave-MW radiation using a free-solvent system [60 °C, PBA (15 mol%) or WC], which reduced the time of the reaction by 32-fold (45 min) and afforded nine amides (S-Aa-Ah and S-Aj) in 80-99% isolated yield and S-Ai in 23% yield. A cytotoxicity assay demonstrated that the amide S-Ag was capable of inhibiting four human tumor cell lines (MCF-7, HCT116, HepG2, and HL-60) with an IC50 ranging from 8.68 to 17.57 μg mL-1. In this study, MW radiation provided an attractive way for faster reactions, improved yields, and cleaner reactions, as well as the synthesis of amide S-Ag with cytotoxic activity.
Synergistic cascade catalysis by metal nanoparticles and Lewis acids in hydrogen autotransfer
Choo, Gerald C. Y.,Miyamura, Hiroyuki,Kobayashi, Shuˉ
, p. 1719 - 1727 (2015/08/12)
Of the many types of catalysis involving two or more catalysts, synergistic catalysis is of great interest because novel reactions or reaction pathways may be discovered when there is synergy between the catalysts. Herein, we describe a synergistic cascade catalysis, in which immobilized Au/Pd bimetallic nanoparticles and Lewis acids work in tandem to achieve the N-alkylation of primary amides to secondary amides with alcohols via hydrogen autotransfer. When Au/Pd nanoparticles were used with metal triflates, a significant rate acceleration was observed, and the desired secondary amides were obtained in excellent yields. The metal triflate is thought to not only facilitate the addition of primary amides to aldehydes generated in situ, but also enhance the returning of hydrogen from nanoparticles to hydrogen-accepting intermediates. This resulted in a more rapid turnover of the nanoparticle catalyst, and ultimately translated into an increase in the overall rate of the reaction. The two catalysts in this co-catalytic system work in a synergistic and cascade fashion, resulting in an efficient hydrogen autotransfer process.
Amidation of Carboxylic Acids with Amines by Nb2O5 as a Reusable Lewis Acid Catalyst
Ali,Siddiki,Onodera, Wataru,Kon, Kenichi,Shimizu, Ken-Ichi
, p. 3555 - 3561 (2015/11/10)
Among 28 types of heterogeneous and homogenous catalysts tested, Nb2O5 shows the highest yield for direct amidation of n-dodecanoic acid with a less reactive amine (aniline). The catalytic amidation by Nb2O5 is applicable to a wide range of carboxylic acids and amines with various functional groups, and the catalyst is reusable. A comparison of the results of the catalytic study and an infrared study of the acetic acid adsorbed on the catalyst suggests that activation of the carbonyl group of the carboxylic acid by Lewis acid sites on Nb2O5 is responsible for the high activity of the Nb2O5 catalyst. Kinetic studies show that Lewis acid sites on Nb2O5 are more water-tolerant than conventional Lewis acidic oxides (Al2O3, TiO2). In comparison with the state-of-the-art homogeneous Lewis acid catalyst for amidation (ZrCl4), Nb2O5 undergoes fewer negative effects from basic additives in the solution, which indicates that Nb2O5 is a more base-tolerant Lewis acid catalyst than the homogeneous Lewis acid catalyst.
Direct amidation of carboxylic acids with amines under microwave irradiation using silica gel as a solid support
Ojeda-Porras, Andrea,Hernández-Santana, Alejandra,Gamba-Sánchez, Diego
supporting information, p. 3157 - 3163 (2015/05/27)
A highly improved and green methodology for the direct amidation of carboxylic acids with amines using silica gel as a solid support and catalyst is described. The scope of this method is exemplified by the use of several aliphatic, aromatic, unsaturated and fatty acids. The reaction is also applied to different primary and secondary amines. Typically, the amines should be aliphatic, but aromatic amines can be used as well, though with lower yields. Several experiments to illustrate the selectivity of this methodology were also carried out with several more functionalized acids and amines. This approach is a substantial improvement over other previously described methods in amide synthesis.
An azobenzene-containing metal-organic framework as an efficient heterogeneous catalyst for direct amidation of benzoic acids: Synthesis of bioactive compounds
Hoang, Linh T. M.,Ngo, Long H.,Nguyen, Ha L.,Nguyen, Hanh T. H.,Nguyen, Chung K.,Nguyen, Binh T.,Ton, Quang T.,Nguyen, Hong K. D.,Cordova, Kyle E.,Truong, Thanh
supporting information, p. 17132 - 17135 (2015/12/04)
An azobenzene-containing zirconium metal-organic framework was demonstrated to be an effective heterogeneous catalyst for the direct amidation of benzoic acids in tetrahydrofuran at 70°C. This finding was applied to the synthesis of several important, representative bioactive compounds.
