- Nickel-Catalyzed Domino Heck-Type Reactions Using Methyl Esters as Cross-Coupling Electrophiles
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While esters are frequently used as traditional electrophiles in substitution chemistry, their application in cross-coupling chemistry is still in its infancy. This work demonstrates that methyl esters can be used as coupling electrophiles in Ni-catalyzed Heck-type reactions through the challenging cleavage of the C(acyl)?O bond under relatively mild reaction conditions at either 80 or 100 °C. With the σ-NiII intermediate generated from the insertion of acyl NiII species into the tethered C=C bond, carbonyl-retentive products were formed by domino Heck/Suzuki–Miyaura coupling and Heck/reduction pathways when organoboron and mild hydride nucleophiles are used.
- Zheng, Yan-Long,Newman, Stephen G.
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p. 18159 - 18164
(2019/11/13)
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- Design, synthesis and pharmacological evaluation of novel antiinflammatory and analgesic O-benzyloxime compounds derived from natural eugenol
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Background: A new series of O-benzyloximes derived from eugenol was synthesized and was evaluated for its antinociceptive and anti-inflammatory properties. Methods: The target compounds were obtained in good global 25-28% yields over 6 steps, which led us to identify compounds (Z)-5,6-dimethoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-one-O-(4- (methylthio)benzyloxime (8b), (Z)-5,6-dimethoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-one-O-4- bromobenzyloxime (8d) and (Z)-5,6-dimethoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-one-O-4- (methylsulfonyl)benzyloxime (8f) as promising bioactive prototypes. Results: These compounds have significant analgesic and anti-inflammatory effects, as evidenced by formalin-induced mice paw edema and carrageenan-induced mice paw edema tests. In the formalin test, compounds 8b and 8f evidenced both anti-inflammatory and direct analgesic activities and in the carrageenan-induced paw edema, with compounds 8c, 8d, and 8f showing the best inhibitory effects, exceeding the standard drugs indomethacin and celecoxib. Conclusion: Molecular docking studies have provided additional evidence that the pharmacological profile of these compounds may be related to inhibition of COX enzymes, with slight preference for COX-1. These results led us to identify the new O-benzyloxime ethers 8b, 8d and 8f as orally bioactive prototypes, with a novel structural pattern capable of being explored in further studies aiming at their optimization and development as drug candidates.
- Da Silva, Rodrigo César,Veiga, Fabiano,Vilela, Fabiana Cardoso,Pereira, André Victor,Da Silva Cunha, Thayssa Tavares,Tesch, Roberta,Viegas, Claudio,Dias, Danielle Ferreira,Giusti-Paiva, Alexandre,Veloso, Marcia Paranho,Fraga, Carlos Alberto Manssour
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p. 1157 - 1166
(2019/10/28)
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- Palladacycle-Phosphine Catalyzed Methylation of Amines and Ketones Using Methanol
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Methylation of amines and ketones with palladacycle precatalyst has been performed using methanol as an environmentally benign reagent. Various ketones and amines undergo methylation reaction to yield monomethylated amines or ketones in moderate to good isolated yields. Moreover, this protocol was tested for the chemoselective methylation of 4-aminobenzenesulfonamide. The scope of the reaction was further extended to the deuteromethylation of ketones.
- Mamidala, Ramesh,Biswal, Priyabrata,Subramani, M. Siva,Samser, Shaikh,Venkatasubbaiah, Krishnan
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p. 10472 - 10480
(2019/08/20)
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- Synthesizing method of indanone compound
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The invention discloses a synthesizing method of an indanone compound. The synthesizing method comprises the following steps of respectively adding a catalyst and an antioxidant into a reaction bottle, then adding a compound shown in a formula (2), adding a solvent, and reacting for 2 to 6h at the temperature of 70 to 120 DEG C under the argon protection atmosphere, so as to obtain the indanone compound, wherein the catalyst is selected from any one of Cu(OAc)2, CuCl2 (copper (II) chloride), CuBr2 (copper (II) bromide), CuO (copper oxide), CuF2 (copper fluoride), Cu(OTf) 2, Cu(OH)2 (copper hydroxide), Cu(NO3)2 (copper nitrate), CuCl (copper chloride), CuBr (copper bromide), CuI (cuprous iodide) and Cu2O (cuprous oxide); the oxidant is tert-butyl hydroperoxide; the solvent is toluene. The synthesizing method has the advantages that a novel concept of the indanone compound is provided; the copper catalyst is used, the price of copper is low, the reserve amount is rich, the environment-friendly effect is realized, and the hydroacylation reaction catalyzed by copper meets the requirements of green chemistry.
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Paragraph 0095; 0096; 0098; 0099; 0102
(2018/11/04)
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- DERIVATIVES OF SULINDAC CAN PROTECT NORMAL CELLS AGAINST OXIDATIVE DAMAGE
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The disclosure provides chemical compounds possessing therapeutic and/or protective properties against oxidative damage. Methods of making such therapeutic and/or protective compounds and associated compositions are also provided, as are methods for their use, which include protecting cells from oxidative damage and/or inhibiting production of ROS in a cell or subject, as well as preventing or reducing the extent of tissue damage caused by an ischemic event in a subject at elevated risk of such an event.
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- Scandium triflate-catalyzed intramolecular Friedel-Crafts acylation with Meldrum's acids: insight into the mechanism
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The intramolecular Friedel-Crafts acylation of arenes with Meldrum's acid derivatives catalyzed by Sc(OTf)3 was reported as a mild and general entry into functionalized 1-indanones. Mechanistic investigations were undertaken to determine the rate-determining step in the acylation sequence using Meldrum's acid, as well as to examine the role of the Lewis acid catalyst. Enolizable Meldrum's acid derivatives react via an acyl ketene intermediate under thermal conditions, while quaternized Meldrum's acid derivatives are thermally stable and only act as effective Friedel-Crafts acylating agents in the presence of a Lewis acid catalyst. The acylation was postulated to proceed through direct acylation of a Lewis acid-activated carbonyl. In the catalytic Friedel-Crafts acylation of Meldrum's acids, triflic acid appeared to be the active catalytic species, with Sc(OTf)3 serving as a very mild and convenient reagent for its delivery.
- Fillion, Eric,Fishlock, Dan
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scheme or table
p. 6682 - 6695
(2011/02/26)
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- Meldrum's acids as acylating agents in the catalytic intramolecular Friedel-Crafts reaction
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(Chemical Equation Presented) The intramolecular Friedel-Crafts acylation of aromatics with Meldrum's acid derivatives catalyzed by metal trifluoromethanesulfonates is reported. Meldrum's acids are easily prepared, functionalized, handled, and purified. The synthesis of polysubstituted 1-indanones from benzyl Meldrum's acids was investigated thoroughly, and it was shown that a variety of catalysts were effective, while accommodating a diversity of functional groups under mild conditions. The scope, limitations, and functional group tolerance (terminal alkene and alkyne, ketal, dialkyl ether, dialkyl thioether, aryl methyl ether, aryl TIPS and TBDPS ethers, nitrile- and nitro-substituted aryls, alkyl and aryl halides) for a variety of 5-benzyl (enolizable Meldrum's acids) and 5-benzyl-5-substituted Meldrum's acids (quaternized Meldrum's acids), forming 1-indanones and 2-substituted-1- indanones, respectively, are delineated. This method was further applied to the synthesis of 1-tetralones, 1-benzosuberones, and the potent acetylcholinesterase inhibitor donepezil. Rate of cyclization as a function of ring size was established for various benzocyclic ketones via competition experiments: 1-tetralones form faster than both 1-indanones and 1-benzosuberones, and 1-benzosuberones cyclize faster than 1-indanones.
- Fillion, Eric,Fishlock, Dan,Wilsily, Ashraf,Goll, Julie M.
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p. 1316 - 1327
(2007/10/03)
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- Method for assaying the sod activity by using a self-oxidizable compound necessary for its implementation, self-oxidizable compounds and preparation thereof
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The method for assaying the SOD (super oxide dismutase) activity in liquid medium is based on the activation of self-oxidization, by SOD activity, of a reactive agent having the general formula (I) wherein either n is 1 or 2, R1 is --OR4 or --NR5 R6 ; R2 is H, --OR4, alkyl (1-6C), --CH2 -- or --CH2 --CH2 --, to form a ring by binding to the phenyl substituent, at meta with respect to R1 ; and R3 is H, alkyl (1-6C) or --OR4 (if R2 is different from --OR4); with R4 being H or alkyl (1-6C); R5 being H, alkyl (1-6C), --CH2 COOH, --C6 H5 COOH or --C6 H5 SO3 H; and R6 is H, alkyl (1-6C) or --CH2 COOH; or n is 1, R1 is --OR4, R2 is --CH2 --O--, in order to form a ring by bonding of O with the phenyl substituent, at meta with respect to R1 ; and R3 is H or --OR4. Application to assaying the SOD activity in a sample, specially a biological sample, particularly by a single measurement and one calibrating curve.
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- NEW DERIVATIVES OF 18-CROWN-6 CONTAINING A METHYLINDANONE FRAGMENT IN THE RING
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New derivatives of 18-crown-6 containing a methylindanone fragment in the ring have been obtained by the acylation of dibenzo-18-crown-6 with unsaturated acids in the presence of polyphosphoric acid.
- Tashmukhamedova, A. K.,Sarieva, G. M.,Levkovich, M. G.,Kamaev, F. G.
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p. 489 - 492
(2007/10/02)
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