56426-35-8Relevant academic research and scientific papers
N-vinylation and N-allylation of 3,5-disubstituted pyrazoles by N-H insertion of vinylcarbenoids
Gill, Agagia,Werz, Udo R.,Maas, Gerhard
, p. 747 - 756 (2015)
A vinylcarbenoid approach toward N-functionalization of NH-pyrazoles is presented. The rhodium(II)- catalyzed reaction of methyl styryl-diazoacetate (1) or dimethyl 2-diazoglutaconate (3) with 3,5-disubstituted pyrazoles gave products of carbenoid N-H insertion in high combined yields, although regioselectivity issues posed by the pyrazole or the vinylcarbenoid moiety as well as positional and configurational isomerism concerning the C,C double bond of the latter led to product mixtures. The ambident reactivity of the vinylcarbenoid derived from 1 could be steered by the catalyst: While Rh2(OAc)4 yielded products of direct carbenoid insertion preferentially, silver(I) catalysis strongly favored reaction at the vinylogous site of the carbenoid resulting in an N-allylation of the pyrazoles.
Design, synthesis, biological evaluation and in silico studies of pyrazole‐based nh2‐acyl oseltamivir analogues as potent neuraminidase inhibitors
Ye, Jiqing,Lin, Lin,Xu, Jinyi,Chan, Paul Kay-Sheung,Yang, Xiao,Ma, Cong
, (2021/05/05)
Oseltamivir represents one of the most successful neuraminidase (NA) inhibitors in the current anti‐influenza therapy. The 150‐cavity of NA was identified as an additional binding pocket, and novel NA inhibitors have been designed to occupy the 150‐cavity
Intramolecular Cyclization of Vinyldiazoacetates as a Versatile Route to Substituted Pyrazoles
Drikermann, Denis,G?rls, Helmar,Kerndl, Valerie,Vilotijevic, Ivan
, p. 1158 - 1162 (2020/07/20)
Vinyldiazo compounds undergo a thermal electrocyclization to form pyrazoles in yields of up to 95percent. The reactions are operationally simple, use readily available starting materials, require no intervention of a catalyst, and enable the synthesis of mono-, di- A nd tri-substituted pyrazoles. With the ability to produce highly substituted pyrazoles and the flexibility in installing various types of substituents, this method constitutes a new entry to this valuable heterocyclic scaffold and may be of interest to all branches of the chemical industry.
New Zinc Catalyst for Hydrosilylation of Carbonyl Compounds
Alshakova, Iryna D.,Nikonov, Georgii I.
, p. 3305 - 3312 (2019/08/28)
A new zinc complex was synthesized and applied in the catalytic hydrosilylation of carbonyl compounds. Optimization of the reaction conditions showed that the presence a substoichiometric amount of methanol accelerates the process significantly. The reaction can proceed at very low catalyst load (down to 0.1 molpercent) under mild reaction conditions. The reaction tolerates the presence of C=C bonds, and thus can be useful for the synthesis of allylic alcohols from α,β-unsaturated aldehydes and ketones.
FUSED TRICYCLIC PYRAZOLO-DIHYDROPYRAZINYL-PYRIDONE COMPOUNDS AS ANTIVIRALS
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, (2019/07/13)
The invention provides compounds of Formula (I) as described herein, along with pharmaceutically acceptable salts, pharmaceutical compositions and pharmaceutical combinations containing such compounds, as well as methods to use these compounds, salts and compositions for treating viral infections, particularly infections caused by hepatitis B virus (HBV), and for reducing the occurrence of serious conditions associated with HBV.
The First Kilogram Synthesis of Beclabuvir, an HCV NS5B Polymerase Inhibitor
Bien, Jeffrey,Davulcu, Akin,Delmonte, Albert J.,Fraunhoffer, Kenneth J.,Gao, Zhinong,Hang, Chao,Hsiao, Yi,Hu, Wenhao,Katipally, Kishta,Littke, Adam,Pedro, Aghogho,Qiu, Yuping,Sandoval, Maria,Schild, Richard,Soltani, Michelle,Tedesco, Anthony,Vanyo, Dale,Vemishetti, Purushotham,Waltermire, Robert E.
, p. 1393 - 1408 (2018/09/06)
The process development and kilogram-scale synthesis of beclabuvir (BMS-791325, 1) is described. The convergent synthesis features the use of asymmetric catalysis to generate a chiral cyclopropane fragment and coupling with an indole fragment via an alkyl
Thermally induced N-S bond insertion reaction of diazo compounds with: N -sulfenylsuccinimides: Synthesis of sulfides and mechanism studies
Zhang, Xiaolu,Zheng, Yang,Qiu, Lihua,Xu, Xinfang
supporting information, p. 70 - 76 (2017/12/27)
A metal-free gem-functionalization reaction of diazo compounds with N-sulfenylsuccinimides via a formal N-S bond insertion process has been reported. The transformation features mild reaction conditions, broad substrate scope and functional group tolerance, offering an efficient approach to sulfide synthesis in moderate to high yields. In addition, the mechanism studies indicate the formation of free carbene under thermal conditions followed by ylide generation, then N-S bond cleavage and C-N bond formation occurred in sequence to give the sulfide products.
Synthesis of Nitrogen Heterocycles via Photochemical Ring Opening of Pyridazine N-Oxides
Portillo, Maribel,Maxwell, Michael A.,Frederich, James H.
, p. 5142 - 5145 (2016/10/14)
A photochemical method for the direct synthesis of 1H-pyrazoles from pyridazine N-oxides was developed. This chemistry features a regioselective approach to nonsymmetrically substituted pyridazine N-oxides. Herein, we highlight the first strategic use of photoinduced ring-opening reactions of 1,2-diazine N-oxides for the preparative synthesis of nitrogen heterocycles.
Development of a simple system for the oxidation of electron-rich diazo compounds to ketones
O'Connor, Nicholas R.,Bolgar, Peter,Stoltz, Brian M.
supporting information, p. 849 - 851 (2016/02/05)
Mild heating of diazo compounds in DMSO furnishes ketone products in moderate to excellent yields. The reaction is particularly effective on electron-rich substrates and exhibits high chemoselectivity, allowing for the use of diazo compounds containing additional oxidation-prone functional groups. This straightforward protocol offers an alternate route to synthetically useful α-ketoesters from readily available aryl diazoacetates.
PAR2 RECEPTOR ANTAGONISTS
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Page/Page column 51, (2014/02/16)
Compounds of formula (I) or pharmaceutically acceptable salts, solvates or hydrates thereof wherein P, Q, X, Y, R1, R2, R3, R10, R11, and R12 are as defined in the claims, and the use those compounds in medicine.
