- Method for promoting acylation of amine or alcohol by carbon dioxide
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The invention relates to a method for promoting acylation of amine or alcohol by carbon dioxide, which comprises the following steps of: mixing an amine compound, carboxylate or thiocarboxylate compound and a reaction solvent under the action of carbon dioxide, and reacting to obtain an amide compound, or under the action of carbon dioxide, mixing the alcohol compound, the thiocarboxylate compound and the reaction solvent [gamma]-valerolactone, and reacting to obtain the ester compound. According to the invention, under the promotion action of carbon dioxide, carboxylate or thiocarboxylate is used as an acylation reagent, and amine and alcohol are converted into amide and ester compounds in the absence of a transition metal catalyst, so that acylation reagents such as acyl chloride or anhydride with irritation and corrosivity are avoided; and the method has the advantages of simple operation, mild reaction conditions, high tolerance of substrate functional groups, strong applicability and high yield, and provides an efficient, reliable and economical preparation method for synthesis of amide and ester compounds.
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Paragraph 0033-0034
(2021/05/29)
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- The immobilized copper species on nickel ferrite (NiFe2O4@Cu): a magnetically reusable nanocatalyst for one-pot and quick reductive acetylation of nitroarenes to N-arylacetamides
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In this study, a green protocol for synthesis of N-arylacetamides was introduced. Magnetically, nanoparticles of the immobilized copper species on nickel ferrite, NiFe2O4@Cu, were synthesized and then characterized using SEM, EDX, XRD, VSM, ICP-OES, BET and XPS analyses. The XPS analysis approved that the immobilized copper species on NiFe2O4 only contain Cu(0) and its oxide form as CuO. The prepared nanocomposite system represented a perfect catalytic activity toward one-pot and quick reductive acetylation of various nitroarenes to the corresponding N-arylacetamides. All reactions were carried out in a mixture of H2O–EtOH (1.5–0.5) within 2–10?min using the combination system of NaBH4 and Ac2O in a one-pot approach and via a two-step procedure. The utilized Cu nanocomposite was magnetically separated from the reaction mixture and reused for 5 consecutive cycles without the significant loss of its catalytic activity.
- Zeynizadeh, Behzad,Shokri, Zahra,Mohammadzadeh, Iman
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p. 859 - 870
(2019/12/24)
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- Biogenic CuFe2O4 magnetic nanoparticles as a green, reusable and excellent nanocatalyst for acetylation reactions under solvent-free conditions
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A convenient green method has been developed for the synthesis of biogenic CuFe2O4 magnetic nanoparticles using tea extracts within a very short reaction time. The prepared nanoparticles with an average size of 8.78 nm have been used as an effective catalyst for the acetylation of various alcohols, phenols and amines in good to excellent yields under solvent-free conditions. The catalyst was characterized by XRD, XPS, VSM, SEM and TEM study. A magnetic study of the fresh and recycled catalyst after the fourth cycle was performed by VSM measurement. The main advantages of this protocol are simple biogenic synthesis of the catalyst, a reusable and heterogeneous catalytic system, and short reaction times with excellent yields.
- Chutia, Rituparna,Chetia, Bolin
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p. 15200 - 15206
(2018/09/29)
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- Impregnated copper on Fe3O4: an efficient magnetically separable nanocatalyst for rapid and selective acylation of amines
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The present paper describes the synthesis of N-arylacetamides through acetylation of arylamines with Ac2O in the presence of magnetically recyclable Fe3O4/Cu NPs. All reactions were carried out efficiently in H2O within 2–10?min to give the products in 89–95% yields. Selective acetylation of amines versus alcohols was carried out successfully with this acetylating system. In addition, acetylation of amines and phenols was taken place with the same reactivity. Reusability of the nanocatalyst was examined 5 times without significant loss of its catalytic activity.
- Shokri, Zahra,Zeynizadeh, Behzad
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p. 2467 - 2474
(2017/10/30)
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- Porous coordination polymers of diverse topologies based on a twisted tetrapyridylbiaryl: Application as nucleophilic catalysts for acetylation of phenols
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Porous coordination polymers (CPs) with partially uncoordinated pyridyl rings based on rationally designed polypyridyl linkers are appealing from the point of view of their application as nucleophilic catalysts. A D2d--symmetric tetradentate organic linker L, that is, 2,2 ',6,6'-tetramethoxy-3,3',5,5'-tetrakis(4-pyridyl)biphenyl, was designed and synthesized for metal-assisted self-assembly aimed at porous CPs. Depending on the nature of the metal ion and the counter anion, the ligand L is found to function as a 3- or 4-connecting building block leading to porous CPs of diverse topologies. The reaction of L with Zn(NO3)2 and Cd(NO3)2 yields porous 2D CPs of "fes" topology, in which the tetrapyridyl linker L serves as a 3-connecting unit with its free pyridyl rings well exposed into the pores. The functional utility of these porous CPs containing uncoordinated pyridyl rings is demonstrated by employing them as efficient heterogeneous nucleophilic catalysts for acetylation of a number of phenols with varying electronic properties and reactivities.
- Seth, Saona,Venugopalan, Paloth,Moorthy, Jarugu Narasimha
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p. 2241 - 2249
(2015/01/30)
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- Compositions for Treatment of Cystic Fibrosis and Other Chronic Diseases
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The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.
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Paragraph 0491
(2015/09/22)
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- Heterobicyclic sphingosine 1-phosphate analogs
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Compounds that have agonist activity at one or more of the S1P receptors are provided. The compounds are sphingosine analogs that, after phosphorylation, can behave as agonists at S1P receptors.
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Page/Page column
(2014/04/18)
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- Synthesis and identification of new flavonoids targeting liver X receptor β involved pathway as potential facilitators of Aβ clearance with reduced lipid accumulation
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Alzheimer's disease (AD) is associated with impaired Aβ degradation in the brain. Enhancing the process of Aβ clearance is an attractive potential AD therapy. Treatment with LXR agonists may reduce Aβ levels in vivo. However, the clinical potential of man
- Hu, Yun,Yang, Yaqi,Yu, Yanjun,Wen, Gesi,Shang, Nana,Zhuang, Wei,Lu, Dihan,Zhou, Binhua,Liang, Baoxia,Yue, Xin,Li, Feng,Du, Jun,Bu, Xianzhang
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p. 6033 - 6053
(2013/09/02)
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- PYRAZOLO[1,5a]PYRIMIDINE DERIVATIVES AS IRAK4 MODULATORS
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Compounds of the formula I or II: wherein X, m, Ar, R1 and R2 are as defined herein. The subject compounds are useful for treatment of IRAK-mediated conditions.
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Page/Page column 78
(2012/02/01)
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- HETEROBICYCLIC SPHINGOSINE 1-PHOSPHATE ANALOGS
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Compounds that have agonist activity at one or more of the SlP receptors are provided. The compounds are sphingosine analogs that, after phosphorylation, can behave as agonists at SlP receptors.
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Page/Page column 29; 58
(2010/05/14)
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- Substituted tetrahydro-quinoline-sulfonamide compounds, their preparation and use as medicaments
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The present invention refers to substituted tetrahydro-quinoline-sulfonamide compounds of general formula (I): a method for their preparation, a medicament comprising these compounds and the use of substituted tetrahydro-quinoline-sulfonamide compounds for the preparation of medicaments for 5-HT6 receptor regulation as well as for the treatment of disorders related thereto.
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Page/Page column 18-19
(2009/02/10)
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- Structurally simple inhibitors of lanosterol 14α-demethylase are efficacious in a rodent model of acute Chagas disease
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We report structure-activity studies of a large number of dialkyl imidazoles as inhibitors of Trypanosoma cruzi lanosterol-14α-demethylase (L14DM). The compounds have a simple structure compared to posaconazole, another L14DM inhibitor that is an anti-Chagas drug candidate. Several compounds display potency for killing T. cruzi amastigotes in vitro with values of EC 50 in the 0.4-10 nM range. Two compounds were selected for efficacy studies in a mouse model of acute Chagas disease. At oral doses of 20-50 mg/kg given after establishment of parasite infection, the compounds reduced parasitemia in the blood to undetectable levels, and analysis of remaining parasites by PCR revealed a lack of parasites in the majority of animals. These dialkyl imidazoles are substantially less expensive to produce than posaconazole and are appropriate for further development toward an anti-Chagas disease clinical candidate.
- Suryadevara, Praveen Kumar,Olepu, Srinivas,Lockman, Jeffrey W.,Ohkanda, Junko,Karimi, Mandana,Verlinde, Christophe L. M. J.,Kraus, James M.,Schoepe, Jan,Van Voorhis, Wesley C.,Hamilton, Andrew D.,Buckner, Frederick S.,Gelb, Michael H.
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experimental part
p. 3703 - 3715
(2010/04/24)
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- SUBSTITUTED TETRAHYDRO-QUINOLINE-SULFONAMIDE COMPOUNDS, THEIR PREPARATION AND USE AS MEDICAMENTS
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The present invention refers to substituted tetrahydro-quinoline-sulfonamide compounds of general formula (I): a method for their preparation, a medicament comprising these compounds and the use of substituted tetrahydro-quinoline-sulfonamide compounds for the preparation of medicaments for 5-HT6 receptor regulation as well as for the treatment of disorders related thereto.
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Page/Page column 10
(2009/02/11)
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- SbCl3 as a highly efficient catalyst for the acetylation of alcohols, phenols, and amines under solvent-free conditions
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Antimony trichloride has been found to be an efficient and expedient catalyst for the acylation of alcohols, phenols, amines, and sugars with acetic anhydride in high yields and in a short reaction time under solvent-free conditions at room temperature. Also, racemization of chiral alcohols and epimerization of sugars were not observed in any of the substrates. Copyright Taylor & Francis Group, LLC.
- Bhattacharya, Asish K.,Diallo, Mamadou A.,Ganesh, Krishna N.
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p. 1518 - 1526
(2008/09/20)
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- Synthesis of 3-acetoxyacetanilide derivatives by means of semmler-wolff-type aromatization reaction of cyclohexane-1,3-dione monooximes
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A novel method for synthesizing 3-acetoxyaniline derivatives from substituted cyclohexane-l, 3-diones is described. This synthetic process includes regioselective formation of cyclohexane-l, 3-dione monooximes 2 and their Semmler-Wolff-type aromatization under very simple reaction conditions. Copyright
- Ishikawa, Teruhiko,Arai, Masaki,Nishiuchi, Hironori,Ishiguro, Hiroshi,Saito, Seiki
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supporting information; experimental part
p. 1066 - 1067
(2009/12/02)
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- N-sulfamoyl-N'-benzopyranpiperidine compounds and uses thereof
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N-sulfamoyl-N′-benzopyranpiperidine compounds of formula I and their physiologically acceptable acid addition salts, pharmaceutical compositions comprising them, processes for their preparation, and their use for the treatment and/or inhibition of glaucoma, epilepsy, bipolar disorders, migraine, neuropathic pain, obesity, type II diabetes, metabolic syndrome, alcohol dependence, and/or cancer, and related concomitant and/or secondary diseases or conditions.
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Page/Page column 8
(2008/06/13)
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- N-SULFAMOYL-N’-BENZOPYRANPIPERIDINES AS INHBITORS OF CARBONIC ANHYDRASES
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The present invention relates to novel N-sulfamoyl-N'-benzopyranpiperidines of general formula (I) and their physiologically acceptable acid addition salts, to pharmaceutical compositions comprising them, processes for their preparation, and their use for the prophylaxis and/or treatment and/or prevention and/or inhibition of glaucoma, epilepsy, bipolar disorders, migraine, neuropathic pain, obesity, type II diabetes, metabolic syndrome, alcohol dependence, and/or cancer, and its concomitant and/or secondary diseases or conditions.
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Page/Page column 15-16
(2008/06/13)
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- Facile catalyzed acylation of alcohols, phenols, amines and thiols based on ZrOCl2·8H2O and acetyl chloride in solution and in solvent-free conditions
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Acylation of heteroatoms (O, N and S) with acetyl chloride based on the use of a catalytic amount of the moisture stable, inexpensive ZrOCl 2?8H2O, proceeds efficiently producing the corresponding acylated products in excellent yields.
- Ghosh, Rina,Maiti, Swarupananda,Chakraborty, Arijit
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p. 147 - 151
(2007/10/03)
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- PYRAZOLE COMPOUNDS
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Compounds of formula (IA) or (IB) or a salt, N-oxide, hydrate or solvate thereof are inhibitors of HSP90, and are of value in the treatment of diseases responsive to HSP90 inhibition such as cancers. In the formulae, Ar is an aryl, aryl(C1-C6 alkyl), aryl(C1-C6 alkyl), heteroaryl, heteroarylaryl(C1-C6 alkyl), or heteroarylaryl(C1-C6 alkyl) group, any of which being optionally substituted in the aryl or heteroaryl part thereof; R1, is hydrogen or optionally substituted Cl-C6 alkyl; R2 is hydrogen, optionally substituted cycloalkyl, cycloalkenyl, C1-C6 alkyl, C1-C6 alkenyl, or Cl-C6 alkynyl; or a carboxyl, carboxamide or carboxyl ester group; and ring A is a non aromatic carbocyclic or heterocyclic ring wherein (i) a ring carbon is optionally substituted, and/or (ii) a ring nitrogen is optionally substituted by a group of formula -(Alk1)p (Cyc)n-(Alk3)m-(Z)r (Alk2)s Q where Alk1, Alk2 and Alk3 are optionally substituted C1-C3 alkyl, Cyc is an optionally substituted carbocyclic or heterocyclic radical; m, n, p, r and s are independently 0 or 1, Z is -0-, -S-, -(C=O)-, -S02-, -C(=O)O-, -OC(=O)-, -NW-, -C(=O)NRA-, -NRAC(=O)-, -SO2NRA- , or -NRASO2- wherein RA is hydrogen or C1-C6 alkyl, and Q is hydrogen or an optionally substituted carbocyclic or heterocyclic radical.
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- Facile catalyzed acylation of heteroatoms using BiCl3 generated in situ from the procatalyst BiOCl and acetyl chloride
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Acylation of a variety of alcohols, phenols, aliphatic and aromatic amines, a thiol and a thiophenol proceeds efficiently using BiCl3 generated in situ from the procatalyst BiOCl and acetyl chloride in a solvent or under solventless conditions, furnishing the corresponding acylated derivatives in very good to excellent yields.
- Ghosh, Rina,Maiti, Swarupananda,Chakraborty, Arijit
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p. 6775 - 6778
(2007/10/03)
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- Synthesis and in-vitro evaluation of platelet aggregation inhibitory activity of paeonol and its analogues
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Paeonol (1-(2-hydroxy-4-methoxyphenyl)ethanone) and a series of substituted 1-(2-hydroxyphenyl)ethanone derivatives were synthesized and screened as inhibitors of platelet aggregation. The compounds with the greatest anti-platelet potential among the series tested were 1-(2,5-dihydroxyphenyl)ethanone (65.36% inhibition at 300 μM against 5 μM ADP), paeonol(36.31%), 1-(2-hydroxy-5-methoxyphenyl)ethanone (24.47%), 1-(2-hydroxy-5-nitrophenyl) ethanone (30.40%) and 1-(5-chloro-2-hydroxy-4-methylphenyl)ethanone (24.43%).
- Akamanchi,Padmawar,Thatte,Rege,Dahanukar
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p. 323 - 329
(2007/10/03)
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- Transacylations with Acyl Derivatives of 4-Pyridones
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Aliphatic and aromatic amines as well as thiols react with N-acyl-4-pyridones (2a, b) and with 4-(benzoyloxy)pyridine (3a) in methylene chloride or chloroform to give the N-substituted amides 4-6 and the thiol esters 7 and 8, respectively, with very good yields.Primary and secondary alcohols react more slowly, tert-butyl alcohol only with 3a to the tert-butyl esters 12 under basic catalysis or with the much more reactive N-(trihaloacetyl)-4-pyridones 3b, c.N-Acetyl-4-pyridone (2a) possesses a much higher acylation potential than N-acetylimidazole (13a).
- Effenberger, Franz,Bessey, Eberhard
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p. 2100 - 2109
(2007/10/02)
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