- Ag2CO3-mediated direct functionalization of alkyl nitriles: Facile synthesis of γ-ketonitriles through nitrile alkylation of enol acetates
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Direct C(sp3)-H functionalization of alkyl nitriles is a low toxic and facile route to nitrile-containing compounds. In this research, the Ag2CO3-mediated nitrile methylenation of enol acetates is developed to prepare γ-ketonitriles through the direct C(sp3)-H oxidative functionalization of acetonitrile. A radical pathway is proposed, and acetonitrile serves both as solvent and CN-containing radical source.
- Cheng, Pi,Wang, Wei,Wang, Lin,Zeng, Jianguo,Reiser, Oliver,Liang, Yun
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p. 1408 - 1412
(2019/05/06)
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- Chemoselective Access to γ-Ketoesters with Stereogenic Quaternary α-Center or γ-Keto Nitriles by Aerobic Reaction of α-Cyanoesters and Styrenes
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Chemoselective access to either γ-ketoesters with a quaternary all-carbon α-stereogenic center or γ-keto nitriles is described by copper-catalyzed aerobic reaction of styrenes with α-cyanoesters. Formal oxo-enolation or oxo-cyanomethylation of styrenes is achieved via a sequence of addition of enolate (or cyanomethyl) radical to olefin and oxidation of the resulting radical adduct. This method starts from abundant and cheap feedstock under aerobic conditions, without any prefunctionalization or the production of stoichiometric metal salts waste, making it very attractive for practical use.
- Zhang, Song-Lin,Wang, Xian-Jin,Yu, Ze-Long
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supporting information
p. 3139 - 3142
(2017/06/23)
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- Preparation γ - par phenyle and γ - ketoester method (by machine translation)
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The invention relates to a process for preparing γ - par phenyle and γ - ketoester method, characterized in that comprises the following experimental procedure: catalyst/ligand/additive under the catalytic action of, in the environment of oxygen, with the α - cyano ester substituted styrene mixed solution for 60 - 100 °C oil bath pot reaction 12 - 20 h; cooling after reaction to the room temperature, by extraction, washing, drying and chromatography, to obtain the product γ - par phenyle and γ - ketoester. The invention of each reaction raw material, catalyst, ligand, additive and solvent are industrial commodities, simple and easy to obtain, the price is cheap, and performance is quite stable, does not need special storage conditions, the operation is convenient. The invention has advantages of low cost, high yield, the process is simple, and less pollution and the like. (by machine translation)
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Paragraph 0026-0030
(2018/04/01)
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- Simple efficient routes for the preparation of pyrazoleamines and pyrazolopyrimidines: Regioselectivity of pyrazoleamines reactions with bidentate reagents
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Simple and efficient routes for the preparation of 2-amino-5-phenyl-4, 5-dihydrofuran-3-carbonitrile (12), 2-oxo-5-phenyl-tetrahydrofuran-3-carbonitrile (13) and the 3, 5-diaminopyrazole derivative 2h were developed. The results of the reactivity profiles of 12 and 2h are reported and the previously investigated reaction of pyrazole-3, 5-diamine (2b) with acrylonitrile to yield compound (31), a N-1 acylation product, is currently justified by using X-ray crystallographic analysis. Taken together, the observation of alkenes and alkynes substitution when reacting with 3, 5-diaminopyrazole derivative 2h is explained by the terminal electron withdrawing group. This pattern of substitution is attributed to involvement of sterically unhindered electrophiles primarily at the N-1 position.
- Moustafa, Moustafa Sherief,Al-Mousawi, Saleh Mohammed,Elnagdi, Mohamed Hilmy
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- Regioselective alkylation of isopropylidene- and cyclohexylidenepropanedinitrile with phenacyl bromides
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Alkylation of isopropylidene- and cyclohexylidenepropanedinitrile with phenacyl bromides gave 2,2-bis(2-aryl-2-oxoethyl)propanedinitriles. Direct alkylation of propanedinitrile with phenacyl bromides afforded only 2-(2-aryl-2-oxoethyl)propanedinitriles.
- Dyachenko,Pavlova
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p. 1693 - 1696
(2016/02/03)
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- Studies with β-oxoalkanonitriles: Simple novel synthesis of 3-[2,6-diaryl-4- pyridyl]-3-oxopropanenitriles
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Heteroaromatization of ethyl 2-cyano-4-oxo-2-(2-oxo-2-arylethyl)-4- arylbutanoates 3a,b with ammonium acetate gave ethyl 2,6-diarylisonicotinates 4a,b. Treatment of the latter with acetonitrile afforded novel β-oxoalkanonitriles 6a,b. Reactions of 6a,b wi
- Riyadh, Sayed M.,Al-Matar, Hamad M.,Elnagdi, Mohamed H.
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experimental part
p. 3140 - 3148
(2009/04/07)
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- Regioselective reactions of phenacyl bromide with active methylene compounds
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The reactivity of phenacyl bromide with active methylene compounds in the presence of alcoholic KOH, BTEAC (PTC), NaOEt and K2CO3 has been studied.
- Padmavathi,Balaiah,Reddy, M. Muralidhar,Reddy, D. Bhaskar
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p. 1519 - 1522
(2007/10/03)
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- 3,3-Disubstituted 1,5-diaryl-1,5-pentanediones as versatile intermediates for spiro heterocycles
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The spiro heterocycles, spiro-4H-pyran pyrazolidinedione/isoxazolidinedione/pyrimidinetrione/thioxopyrimidinedione and spiro-4H-pyran aminopyrazolidinone/isoxazolidinone/hydroxypyrimidinone/mercaptopyrimidinone have been prepared from 3,3-disubstituted 1,5-diaryl-1,5-pentanedione. All the compounds have been characterised by spectral parameters.
- Padmavathi,Balaiah,Reddy, K. Venugopal,Padmaja,Reddy, D. Bhaskar
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p. 1670 - 1675
(2007/10/03)
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- Synthesis and anti-HIV-1 activity of new delavirdine analogues carrying arylpyrrole moieties
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In our search for novel anti-human immunodeficiency virus (HIV)-1 agents, 14 delavirdine analogues were synthesized and evaluated as potential anti-HIV-1 agents in cell-based assays. Compound 1Aa exhibited potent and selective anti-HIV-1 activity in acutely infected MT4 cells, with effective concentration (EC50) values in the submicromolar range.
- Pinna,Loriga,Murineddu,Grella,Mura,Vargiu,Murgioni,La Colla
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p. 1406 - 1411
(2007/10/03)
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- Synthesis and dopamine D2-like receptor binding affinity of substituted 5-phenyl-pyrrole-3-carboxamides.
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A series of 5-p-substituted phenyl-pyrrole-3-carboxamide derivatives was designed as hybrid analogs of the dopamine D2-like 5-phenyl-pyrrole and heterocyclic carboxamide antipsychotics. The title compounds were synthesized and evaluated for dopamine D2-like receptor by means of [3H]YM-09151-2 receptor binding assay. The compound bearing a 1-ethyl-2-methyl-pyrrolidine moiety as the basic part of 5-phenyl-pyrrole-3-carboxamide derivative 1a together with its 2-chloro analog 1f were found to possess affinity in the low micromolar range. Substituted phenyl-pyrrolecarboxamides containing groups such as F, Cl, NO2, CH3, at the 4-position of the phenyl ring, gave ligands with lower D2-like affinity.
- Pinna,Curzu,Sechi,Chelucci,Maciocco
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p. 542 - 550
(2007/10/03)
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