- Photoredox Activation of Formate Salts: Hydrocarboxylation of Alkenes via Carboxyl Group Transfer
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A photoredox activation mode of formate salts for carboxylation was developed. Using a formate salt as the reductant, carbonyl source, and hydrogen atom transfer reagent, a wide range of alkenes can be converted into acid products via a carboxyl group tra
- Huang, Yan,Hou, Jing,Zhan, Le-Wu,Zhang, Qian,Tang, Wan-Ying,Li, Bin-Dong
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p. 15004 - 15012
(2021/12/14)
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- Cu/PCy3-Catalyzed Formal Carbene Insertion into Electron-Deficient C?H Bonds
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A carbene insertion into electron-deficient C?H bonds of 1,3-diesters, β-ketoesters, β-ketonitriles, and malononitriles was realized by using CuCN/PCy3 as the catalyst. The reaction provides a straightforward approach to the synthetically important multi-substituted succinic acid derivatives. A plausible reaction mechanism with cyclopropanation/ring opening as key steps was proposed based on control experiments.
- Ren, Yuan-Yuan,Mao, Hong-Xiang,Hu, Meng-Yang,Zhu, Shou-Fei,Zhou, Qi-Lin
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p. 4267 - 4271
(2020/07/06)
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- Harnessing Applied Potential: Selective β-Hydrocarboxylation of Substituted Olefins
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The construction of carboxylic acid compounds in a selective fashion from low value materials such as alkenes remains a long-standing challenge to synthetic chemists. In particular, β-addition to styrenes is underdeveloped. Herein we report a new electrosynthetic approach to the selective hydrocarboxylation of alkenes that overcomes the limitations of current transition metal and photochemical approaches. The reported method allows unprecedented direct access to carboxylic acids derived from β,β-trisubstituted alkenes, in a highly regioselective manner.
- Alkayal, Anas,Buckley, Benjamin R.,Malkov, Andrei V.,Montanaro, Stephanie,Tabas, Volodymyr,Wright, Iain A.
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supporting information
(2020/02/13)
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- Stereoselective One-Pot Synthesis of cis-1,2-Dicyanoalkenes from 1,1-Bis(benzenesulfonyl)alkenes and KCN
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An efficient synthesis of cis-1,2-dicyanoalkenes by the reaction of 1,1-bis(benzenesulfonyl)alkenes with KCN was developed. This reaction was conducted in the presence of tetrabutylammonium bromide and NH4Cl/K3PO4 under phase-transfer conditions. A series of cis-1,2-dicyanoalkenes were obtained in good to high yields. Further transformation of the obtained product allows for access to imide and dicarboxylic acid compounds.
- Zhang, Yue,Wei, Yi,Li, Shen,Ma, Jun-An
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p. 199 - 203
(2019/01/04)
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- Preparation method and application of tetrahydroisoquinoline derivative
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The invention discloses a preparation method of a tetrahydroisoquinoline derivative. The tetrahydroisoquinoline derivative is prepared by subjecting 1-(tetrapyrrolidin-1-yl)-1,2,3,4-tetrahydroisoquinoline and 2,3-dihydro-indene-3-one-1-carboxylic acid to condensation. Process conditions are optimized so that preparation steps are simplified. Agents used in the preparation are pollution free. The prepared tetrahydroisoquinoline derivative 1-(tetrapyrrolidin-1-methyl)-2-(2,3-dihydro-indene-3-one-1-carbonyl)-1,2,3,4-tetrahydroisoquinoline can provide good calming effect against neuropathic pain.The tetrahydroisoquinoline derivative has high medical value in drug compositions for pain treatment and in replacing dependent analgesics, such as morphine.
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Paragraph 0035-0038
(2019/03/08)
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- Method for synthesizing succinic acid compounds
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The invention provides a method for synthesizing succinic acid compounds. The method specifically comprises the following steps: adding a substrate, a photocatalyst and an alkali into a reaction tube,adding a reducing agent and a solvent under the atmosphere of CO2, conducting reacting under the irradiation of visible light, carrying out quenching treatment after the raw materials react completely, and then conducting separating and purifying to obtain a dicarboxylated product of olefin, namely a succinic acid compound. The photocatalyst is 4CzIPN or Ir[(ppy)2(dtbppy)]PF6 and the like, and the reaction substrate comprises 1,1-diaryl ethylene, a monoaryl substituted olefin compound, an acrylate compound and allene. According to the scheme provided by the invention, the reaction conditionsare mild, the applicability of the reaction substrate is wide, and the yield is basically not influenced under the condition that the reaction substrate is amplified to the gram scale; and meanwhile,the invention overcomes the defects of high toxicity of reagents and harsh reaction conditions in the prior art, and has a good industrial application prospect.
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Paragraph 0028-0036; 0040
(2019/08/01)
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- Direct β-Selective Hydrocarboxylation of Styrenes with CO2 Enabled by Continuous Flow Photoredox Catalysis
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The direct β-selective hydrocarboxylation of styrenes under atmospheric pressure of CO2 has been developed using photoredox catalysis in continuous flow. The scope of this methodology was demonstrated with a range of functionalized terminal styrenes, as well as α-substituted and β-substituted styrenes.
- Seo, Hyowon,Liu, Aofei,Jamison, Timothy F.
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supporting information
p. 13969 - 13972
(2017/10/17)
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- Discovery, stereospecific characterization and peripheral modification of 1-(pyrrolidin-1-ylmethyl)-2-[(6-chloro-3-oxo-indan)-formyl]-1,2,3,4-tetrahydroisoquinolines as novel selective κ opioid receptor agonists
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A novel series of 1-(pyrrolidin-1-ylmethyl)-2-[(3-oxo-indan)-formyl]-1,2,3,4-tetrahydroisoquinoline derivatives maj-3a-maj-3u were synthesized and evaluated in vitro for their binding affinity at κ-opioid receptors. Maj-3c displayed the highest affinity for κ-opioid receptors (Ki = 0.033 nM) among all the compounds evaluated. Furthermore, all four stereoisomers of compound 3c were prepared, and (1S,18S)-3c was identified as the most potent (Ki = 0.0059 nM) κ-opioid receptor agonist among the four stereoisomers. Maj-3c produced significant antinociception (ED50 = 0.000406 mg kg-1) compared to U-50,488H and original BRL 52580 in the acetic acid writhing assay, but its strong sedative effect (ED50 = 0.000568 mg kg-1) observed in the mouse rotation test reduced its druggability. To minimize the central nervous system side effects, a series of hydroxyl-containing analogs of maj-3c were synthesized, and maj-11a was found to be a potent κ-opioid receptor agonist (Ki = 35.13 nM). More importantly, the dose for the sedative effect (ED50 = 9.29 mg kg-1) of maj-11a was significantly higher than its analgesic dose (ED50 = 0.392 mg kg-1), which made it a promising peripheral analgesic candidate compound with weak sedative side effects.
- Gan, Zong-Jie,Wang, Yu-Hua,Xu, Yun-Gen,Guo, Ting,Wang, Jun,Song, Qiao,Xu, Xue-Jun,Hu, Shi-Yuan,Wang, Yu-Jun,Wang, De-Chuan,Sun, De-Zhu,Zhang, Di,Xi, Tao,Li, Hao-Dong,Zhang, Hai-Bo,Hang, Tai-Jun,Lu, Hong-Guo,Liu, Jing-Gen
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p. 5656 - 5673
(2015/05/27)
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- DERIVATIVES OF 2-PYRIDIN-2-YL-PYRAZOL-3(2H)-ONE, PREPARATION AND THERAPEUTIC USE THEREOF AS HIF ACTIVATORS
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The present invention relates to novel substituted dihydropyrazolone derivatives, to their preparation and to their therapeutic use as activators of the transcription factor HIF.
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Page/Page column 26
(2011/12/13)
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- TETRAHYDRO ISOQUINOLINE DERIVATIVES, PREPARATION METHODS AND MEDICINAL USES THEREOF
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A kind of tetrahydro isoquinoline derivatives (I), their preparation methods, medicine compositions and medicinal uses thereof, especially their uses as κ-opioid receptor excitant in pain relieving, which belongs to the medicine chemistry. The substituents R1, R2, R3, R4 of general formula (I) are defined as the description.
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Page/Page column 8
(2009/04/23)
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- Tetrahydro isoquinoline derivatives, preparation methods and medicinal uses thereof
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A kind of tetrahydro isoquinoline derivatives (I), their preparation methods, medicine compositions and medicinal uses thereof, especially their uses as kappa-opioid receptor excitant in pain relieving, which belongs to the medicine chemistry. The substituents R1, R2, R3, R4 of general formula (I) are defined as the description.
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Page/Page column 6
(2009/12/02)
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- Efficient electrochemical dicarboxylations of arylacetylenes with carbon dioxide using nickel as the cathode
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The electrochemical dicarboxylation of arylacetylenes with carbon dioxide could be smoothly achieved in an undivided cell using Ni as the cathode and Al as the anode with n-Bu4NBr-DMF as the supporting electrolyte, at a constant current under CO2 pressure of 3 MPa and room temperature in the absence of additional catalysts. The corresponding aryl-maleic anhydrides and 2-arylsuccinic acids were afforded in excellent total yields (82-94%). Under anhydrous conditions, an unsaturated aryl-maleic anhydride as the main product was obtained, while the presence of H2O would lead to the formation of saturated 2-arylsuccinic acids. The results of cyclic voltammetric experiments show that a nickel cathode itself plays the catalytic role in the reduction reaction of arylacetylenes with CO2.
- Yuan, Gao-Qing,Jiang, Huan-Feng,Lin, Chang
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p. 5866 - 5872
(2008/09/21)
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- Simple synthesis of arylsuccinic acids
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Alkylation of arylacetonitriles with potassium chloroacetate proceeds selectively leading to 3-cyano-3-arylpropionic acids, which are directly hydrolyzed to arylsuccinic acids.
- Makosza,Marcinowicz
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p. 1311 - 1312
(2007/10/03)
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- Efficient electrochemical dicarboxylation of phenyl-substituted alkenes: Synthesis of 1-phenylalkane-1,2-dicarboxylic acids
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Electrochemical dicarboxylation of phenyl-substituted alkenes in the presence of atmospheric pressure of carbon dioxide with a platinum plate cathode and a magnesium rod anode readily took place efficiently in a DMF solution containing 0.1 M Et4NClO4 to give the corresponding 1,2-dicarboxylic acids in high yields.
- Senboku,Komatsu,Fujimura,Tokuda
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p. 418 - 420
(2007/10/03)
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- 1,4-Conjugate addition of the Reformatsky reagent to α-nitrostyrenes: A new synthesis of γ-nitroesters
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α-Nitrostyrenes react with the Reformatsky reagent to yield the corresponding 1,4-addition products. The reaction represents a practical and convenient route to ethyl 3-aryl-4-nitrobutanoates.
- Menicagli, Rita,Samaritani, Simona
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p. 1425 - 1432
(2007/10/03)
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- "ONE-POT" SYNTHESIS OF DISYMMETRICALLY α,α'-DISUBSTITUTED SUCCINIC ANHYDRIDES PRECURSORS
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A "one-pot" synthesis for disymmetrically α,α'-disubstituted succinic anhydrides precursors isreported in the present paper.Substituents are aryl, primary or secondary alkyl groups.This reaction represents a simple and quick method with fair yields.
- Dana, A.,Campagnole, M.,Bourgeois, M.J.,Montaudon, E.
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p. 2981 - 2988
(2007/10/03)
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- Remarkable Selectivity in the Reaction of 1-Trityl-2-lithioimidazoles with t-Butyl Halogenoacetates
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2-Lithio-1-triphenylmethylimidazoles react with t-butyl halogenoacetates to give a variety of products, the nature of which is cleanly determined by the halogen atom.With chloroacetate the products are chloromethyl ketones, while bromacetate gives di-t-butyl imidazolesuccinates, and iodoacetate yields iodoimidazoles.In each case 50percent of the parent triphenylmethylimidazole is recovered from the reaction.When the triphenylmethyl substituent is replaced by the N,N-dimethylsulfamoyl group, reaction with bromoacetate is suppressed, but t-butyl chloroacetate and iodoacetate again give chloroketones and aryl iodides respectively.
- Coutts, Ian G. C.,Jieng, Shende,Khandelwahl, Ghanshyam D.,Wood, Michael L.
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p. 857 - 860
(2007/10/02)
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- Hydroformylation of cinnamic acid derivatives catalyzed by rhodium complexes
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The hydroformylation of methyl cinnamate catalyzed by various rhodium complexes affords the aldehyde 1a with good chemo- and regio-selectivity, while in the case of methyl p-chlorocinnamate the predominant reaction is the substrate hydrogenation. Higher yields of the desired aldehydes 1a and 1b are obtained by hydroformylation of the cinnamaldehyde and p-chlorocinnamaldehyde diethylacetal, respectively, under the same reaction conditions. These aldehyde products are valuable drug precursors.
- Botteghi, C.,Paganelli, S.
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p. C18 - C21
(2007/10/02)
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- STERICALLY SCREENED HALOGENOCYCLOBUTANONES VI. SYNTHESIS OF 3-FORMYLPROPIONIC ACIDS FROM DICHLOROCYCLOBUTANONES
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3-Formylpropionic acids can be obtained with good yields by the treatment of 2,2-dichlorocyclobutanones with an aqueous solution of potassium hydroxide.
- Bessmertnykh, A. G.,Donskaya, N. A.
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p. 279 - 284
(2007/10/02)
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- Reductive Arylation of Maleic and Fumaric Acid Derivatives by Arenediazonium and Titanium(III) Salts
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The titanium(III)-induced decomposition of substituted benzenediazonium salts in the presence of maleic and fumaric acids, alkyl esters, amides, and nitriles gives the corresponding arylsuccinic acid derivatives.
- Citterio, Attilio,Cominelli, Alberto,Bonavoglia, Francesco
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p. 308 - 309
(2007/10/02)
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- Studies on the Autoxidation of 1-Phenylbuta-1,3-diene and 2-Phenylbuta-1,3-diene
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Hydrogenation of the polymeric peroxides formed during the autoxidation of 1-phenylbuta-1,3-diene (1) and 2-phenylbuta-1,3-diene (10) at 50 deg C in an autoclave yielded 1-phenylbutane-3,4-diol (5) and 2-phenylbutane-1,4-diol(12), respectively.The LiAlH4 reduction of 1-phenylbuta-1,3-diene oxidate (50 deg C) yielded cinnamyl alcohols (4) as a major product.The oxygen-containing polymeric products formed along with Diels-Alder dimers during the oxidation of the title substances at 140 deg C showed no degradation after subjecting to hydrogenation and are therefore considered as polyethers.
- Blau, K.,Voerkel,V.,Willecke, L.
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- Enamines; 45. A New Simple Synthesis of 2-Phenylsuccinic Acids
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A simple route to 2-phenylsuccinic acids consists of the reaction of 1,1-dimorpholinoethene with β-nitrostyrenes at room temperature and hydrolysis of the 1:1 adduct thus obtained with hydrochloric acid.The method affords good overall yields of 2-phenylsuccinic acids.
- Rossi, Elisabetta,Sassano, Silvia,Stradi, Riccardo
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p. 765 - 766
(2007/10/02)
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- PREPARATION AND SOME REACTIONS OF 4- AND 5-ARYL-4,5-DIHYDROPYRIDAZIN-3(2H)-ONES
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Efficient preparations of 4- and 5-phenyl-4,5-dihydropyridazin-3(2H)-ones have been developed, the main reactions of these compounds have been studied, and the synthetic routes have been used to give analogues with substituents in the phenyl rings.In the best synthesis of the 4-phenyldihyropyridazinone (72 percent overall yield) the product was obtained from phenylacetic acid by three simple stages.This approach was applied in preparations of the 2- and 4-hydroxyphenyl compounds and, in conjunction with a recent method for amine protection, the 4-aminophenyl analogue.A four stage synthesis starting from benzaldehyde gave the 5-phenyldihydropyridazinone in 47 percent overall yield; hydroxybenzaldehydes were similarly converted into 5-(allyloxyphenyl)dihydropyridazinones.Oxidation to phenylpyridazinones occured more readily with the 4- and 5-phenyldihydropyridazinones than with the 6-phenyl isomer.The 4- and 5-dihydropyridazinones were smoothly reduced to tetrahydropyridazinones by hydrogenation over platinum but were uneffected by palladium in the presence of hydrazine or cyclohexene.
- Breukelman, Stephen P.,Meakins, G. Denis
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p. 1627 - 1636
(2007/10/02)
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- 1,1-Alkanediol dicarboxylate linked antibacterial agents
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Useful antibacterial agents in which a penicillin and/or a beta-lactamase inhibitor are linked via 1,1-alkanediol dicarboxylates are of the formula STR1 where A is the residue of certain dicarboxyic acids, R3 is H or (C1 -C3), n is zero or 1 such that when n is zero R is P or B and R1 is the residue of certain esters, H or a salt thereof; and when n is 1, one of R and R1 is P and the other is B, and P is STR2 where R2 is H or certain acyl groups, and B is the residue of a beta-lactamase inhibiting carboxylic acid; a method for their use, pharmaceutical compositions thereof and intermediates useful in their production.
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- OXIDATIVE COUPLING OF CARBOXYLIC ACID DIANIONS
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The conditions, scope, and stereochemical consequences of a versatile approach to succinic acid derivatives are described.
- Belletire, J. L.,Spletzer, E. G.,Pinhas, A. R.
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p. 5969 - 5972
(2007/10/02)
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