- A novel and efficient amidation of 2-aminothiazole
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A facile and efficient method has been developed for the synthesis of novel thiazolyl carboxamide derivatives by direct reaction of the corresponding esters and 2-aminothiazole. Treatment of 2-aminothiozole with various carboxylic esters in the presence of t-butylmagnesium chloride provides the biologically significant thiazolyl carboxamide derivatives in good to excellent yields.
- Choi, Minho,Won, Sun-Woo,Jo, Hyeju,Viji, Mayavan,Seo, Seung-Yong,Lee, Yeon-Ju,Lee, Hyi-Seung,Lee, Heesoon,Hong, Jin Tae,Kwak, Young-Shin,Jung, Jae-Kyung
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- Design, synthesis and biological evaluation of new 1,3-thiazole derivatives as potential anti-inflammatory agents
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Thiazoles are widely recognized as nuclei of great value for obtaining molecules with various biological activities, including analgesic, anti-inflammatory, anti-HIV, antidiabetic, antitumor and antimicrobial. A library of 26 thiazole derivatives as fragments were designed, synthesized and evaluated for their anti-inflammatory activities. Some screened compounds showed promising results and were found to be potent in the series by inhibiting LPS-induced TNFα and IL-8 release with IC50 values in μM range without cytotoxic activity.
- Modri?, Marina,Bo?i?evi?, Marin,Faraho, Ivan,Bosnar, Martina,?kori?, Irena
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- Co2(CO)8as a Solid CO (g) Source for the Amino Carbonylation of (Hetero)aryl Halides with Highly Deactivated (Hetero)arylamines
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Carbonylation of (hetero)aryl iodides/bromides with highly deactivated 2-aminopyridines using Pd-Co(CO)4 bimetallic catalysis is accomplished. The use of Co2(CO)8 as a solid CO(g) source enhanced reaction rates observed when compared to CO(g), and excellent yields highlight the versatility of the developed protocol. A wide range of electronically and sterically demanding heterocyclic amines and (hetero)aryl iodides/bromides employed for this study resulted in excellent yields of amino carbonylated products. The developed methodology was further extended to synthesize Trypanosome brucie and luciferase inhibitors.
- Cheruku, Srinivas,Sajith, Ayyiliath M.,Narayana, Yatheesh,Shetty, Poornima,Nagarakere, Sandhya C.,Sagar, Kunigal S,Manikyanally, Kumara N.,Rangappa, Kanchugarkoppal Subbegowda,Mantelingu, Kempegowda
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p. 5530 - 5537
(2021/05/07)
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- Solar and visible-light active nano Ni/g-C3N4photocatalyst for carbon monoxide (CO) and ligand-free carbonylation reactions
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In this study, we investigate the amino and alkoxycarbonylation reaction between various substituted aryl halides, benzyl iodides, and iodocyclohexane with different types of amines and alcohols in the absence of carbon monoxide gas and ligands. Similar reactions are carried out at high temperatures, in the presence of appropriate ligands, stoichiometric amounts of bases, and gaseous carbon monoxide, which endanger the health of organic chemists. We present a novel method that does not utilize ligands, bases, gaseous CO, and special conditions. This procedure is a redox reaction carried out by new economic nano Ni/g-C3N4at room temperature and under visible light. Mo(CO)6was used toin situgenerate CO, to resolve the problems caused by the use of CO gas. This protocol has the ability to be used on a gram scale by using a continuous flow reactor.
- Hosseini-Sarvari, Mona,Akrami, Zahra
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p. 956 - 969
(2021/02/26)
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- N-(thiazol-2-yl)benzamide derivatives as a new series of supramolecular gelators: Role of methyl functionality and S?O interaction
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A new series of N-(thiazol-2-yl) benzamide derivatives were synthesized, characterized and investigated for their gelation behavior with the aim to elucidate the role of methyl functionality and multiple non-covalent interactions on gelation/non-gelation
- Yadav, Priyanka,Ballabh, Amar
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- Nickel/briphos-catalyzed transamidation of unactivated tertiary amides
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The transamidation of tertiary amides was achieved via nickel catalysis in combination with briphos ligands. N-Methyl-N-phenylbenzamide derivatives reacted with primary amines in the presence of NiCl2/briphos L4 to provide the transamidated products in moderate to good yields. Primary aromatic amines delivered higher product yields than aliphatic amines.
- Kim, Hyunwoo,Lee, Sunwoo,Shin, Taeil,Yang, Dahyeon
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supporting information
p. 6053 - 6057
(2020/10/27)
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- Electrochemical: N-acylation synthesis of amides under aqueous conditions
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An electrochemical N-acylation of carboxylic acids with amines was reported. The sustainable TBAB electrocatalysis proceeded with excellent chemoselectivity and positional selectivity, and with ample scope, allowing electrochemical N-acylation under mild reaction conditions at room temperature in water. Moreover, the synthetic utility of the current method is demonstrated by the synthesis of melatonin.
- Ke, Fang,Xu, Yiwen,Zhu, Suning,Lin, Xiaoyan,Lin, Chen,Zhou, Sunying,Su, Huimin
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supporting information
p. 4329 - 4333
(2019/08/21)
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- Method for preparing derivatives of benzamide under microwave condition in aqueous phase
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The invention discloses a method for preparing derivatives of benzamide under a microwave condition in an aqueous phase. A coupling reaction is carried out between substituted benzoic acid and amine under the microwave condition in the aqueous phase. The method for preparing the derivatives of benzamide is environmentally friendly, easy and convenient to operate, safe, low in cost and efficient. Compared with the prior art, the method can be applicable to a large number of functional groups, is high in yield, produces fewer by-products, and further is easy to operate, safe, low in cost and environmentally friendly. A formula is shown in the description.
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Paragraph 0019; 0066
(2019/03/28)
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- Potassium tert-Butoxide Prompted Highly Efficient Transamidation and Its Coordination Radical Mechanism
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A simple and highly efficient protocol was developed for the transamidation of N,N-disubstituted amides with primary amines in the presence of tBuOK, affording desired products in good to excellent yields. This reaction proceeded under nitrogen atmosphere and featured extensive substrate tolerance. Experimental investigation suggested that a coordination radical process enhanced this transformation.
- Tan, Zhiyong,Li, Zhenhua,Ma, Yao,Qin, Jinjing,Yu, Chuanming
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supporting information
p. 4538 - 4545
(2019/07/18)
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- Aminothiazoles and aminothiadiazoles as nucleophiles in aminocarbonylation of iodobenzene derivatives
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Various 2-, 3- and 4-substituted iodobenzenes were aminocarbonylated using aminothiazole and aminothiadiazole derivatives in palladium-catalysed reaction. The reaction is chemospecific toward the corresponding carboxamides. Consequently, the application o
- Gergely, Máté,Kollár, László
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p. 2030 - 2040
(2018/03/21)
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- Imidazolium-supported benzotriazole: an efficient and recoverable activating reagent for amide, ester and thioester bond formation in water
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An efficient and recyclable imidazolium-supported benzotriazole reagent (Im-CH2-BtH) as a novel synthetic auxiliary has been synthesized and its utility as a carboxyl group activating reagent via the formation of stable imidazolium-supported acyl benzotriazoles was explored for the synthesis of amides, esters and thioesters in water under microwave conditions. The reagent was reused five times without any noticeable loss in activity. It is moisture insensitive and highly stable under thermal and aerobic conditions. The application of imidazolium-supported N-acetyl benzotriazole leads to synthesis of paracetamol on the gram scale under greener conditions in 93% yield.
- Shakoor, S.M. Abdul,Choudhary, Sunita,Bajaj, Kiran,Muthyala, Manoj Kumar,Kumar, Anil,Sakhuja, Rajeev
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p. 82199 - 82207
(2015/10/12)
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- Direct synthesis of amides from coupling of alcohols and amines catalyzed by ruthenium(II) thiocarboxamide complexes under aerobic conditions
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Four octahedral ruthenium(II) thiocarboxamide complexes of the general formula [RuClCO(AsPh3)2(L)] (L = N-substituted pyridine-2-thiocarboxamide) incorporating carbonyl and triphenylarsine have been synthesized from the reaction of 1 equiv of ruthenium precursor [RuHClCO(AsPh3)3] with 1 equiv of thiocarboxamide ligands in refluxing ethanol in the presence of base. All the new complexes have been fully characterized by means of elemental analysis, IR, UV-vis, and NMR spectral methods. Molecular structures of all the complexes were determined by X-ray crystallography, which confirm the coordination mode of thiocarboxamide and reveal the presence of a distorted octahedral geometry around the Ru ion. All the ruthenium(II) thiocarboxamide complexes were generated as highly efficient catalysts for synthesis of secondary or tertiary amides by coupling of amines and alcohols with low catalyst loading, and the maximum yield was obtained up to 97%. The coupling reaction can be readily carried out under mild aerobic conditions, and release of water is the only byproduct. Further, the effect of substituents of the ligand, solvents, reaction temperature, time, and catalyst loading on the catalytic activity of the complexes has been investigated. A plausible mechanism is proposed for the synthesis of amides via hemiaminal as intermediate through an oxidation of an alcohol to aldehyde.
- Sindhuja, Elangovan,Ramesh, Rengan,Balaji, Sundarraman,Liu, Yu
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p. 4269 - 4278
(2014/12/09)
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- Reaction of 2-Aminothiazoles with Reagents containing a C-Halogen and a C=O Electrophilic Centre
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Seven reagents of different types having in common a C-Hal and a C=O electrophilic centre have been used in a study of their reactions with 2-aminothiazoles.Three reagents, CHBrAc2 and ROCHBrCO2Et (R = Me, Ph), gave imidazothiazoles, thus providing useful routes to the 5-acetyl and 5-ethoxycarbonyl derivatives.Unexpectedly, the solvent (acetone) was involved in the reaction of the fourth reagent, CHBr(CO2Et)2, with 2-aminothiazole which led to 5,5-di(ethoxycarbonyl)-6,6-dimethyl-5,6-dihydroimidazothiazole (yield 81percent).With the last three reagents (AcCHBrNO2, BzCHBrCN and ICH2CO2C6H4NO2-p) the outcome was simpler, viz., the formation of 2-amidothiazoles.It is proposed that electrophilic attack by the endo-N of the 2-aminothiazole is the first step in all cases.This occurs at the C-Hal centre of the first four reagents and is followed by cyclisation to the exo-N.In the last three electrophiles the presence of the groups well suited to leaving as stabilised anions favours addition to the C=O group; the intermediates so formed subsequently isomerise to the more stable exo-N substituted products.
- Compton, Victoria J.,Meakins, G. Denis,Raybould, Amanda J.
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p. 2029 - 2032
(2007/10/02)
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