- Copper(II)-mediated formation of oxazole-4-carbonitrile from acetophenone and coordinated cyanide anion: Via a radical coupling
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A protocol for the direct synthesis of 5-aryloxazole-4-carbonitrile from acetophenone was first described with potassium ferricyanide as a cheap and low toxicity cyanide reagent, in which, multiple bond formation was implemented via an oxygen mediated radical mechanism. Potassium ferricyanide played a dual role as a CN source and also as a coupling partner for the cyclization of oxazole.
- Xu, Congjun,Qin, Mingze,Yi, Jun,Wang, Yanjing,Chen, Yanfeng,Zhang, Bingfu,Zhao, Yanfang,Gong, Ping
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Read Online
- Reaction method for selectively synthesizing oxazole-4-carboxylic ester
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The invention provides a reaction method for selectively synthesizing oxazole-4-carboxylic ester, which comprises the following steps of reacting by taking aromatic aldehyde serving as a raw material,cuprous salt serving as a catalyst and organic amine serving as an additive in a solvent in a nitrogen or argon atmosphere to obtain oxazole-4-carboxylic ester serving as a main product. The synthesis method provided by the invention has the characteristics of atom economy and high selectivity, uses substituted benzaldehyde and aromatic heterocyclic formaldehyde as substrates, and has the advantages of low price, easiness in obtaining, no generation of waste acid and waste gas and the like; the metal copper salt is used for catalyzing, so that the method has the advantages of low cost, easiness in obtaining, wide substrate applicability, simple post-treatment, good reaction selectivity and the like.
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Paragraph 0019; 0020
(2021/03/24)
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- Silver-Induced [3+2] Cycloaddition of Isocyanides with Acyl Chlorides: Regioselective Synthesis of 2,5-Disubstituted Oxazoles
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A silver-induced cycloaddition of isocyanides with acyl chlorides has been developed. This transition metal-catalyzed strategy provides an effective and scalable approach for the formation of 2,5-disubstituted oxazoles in good to high yields. The employed silver-based MOF catalyst can be efficiently recycled without compromising the yield.
- Liu, Jian-Quan,Shen, Xuanyu,Shatskiy, Andrey,Zhou, Enlong,K?rk?s, Markus D.,Wang, Xiang-Shan
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p. 4272 - 4275
(2019/07/19)
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- Synthesis of oxazoles by silver catalysed oxidative decarboxylation-cyclization of α-oxocarboxylates and isocyanides
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A silver catalysed synthesis of oxazoles by the oxidative decarboxylation-cyclization of α-oxocarboxylates and isocyanides was developed. This method provided a novel strategy to construct oxazole rings compared to traditional methods. Mechanistic investigations such as operando IR, EPR and radical inhibition experiments were carefully done and confirmed the acyl cation and Ag(ii) as the intermediates in this transformation, and the involvement of a radical decarboxylative process.
- Ma, Yiyang,Yan, Zhiyuan,Bian, Changliang,Li, Ke,Zhang, Xiaowen,Wang, Mengfan,Gao, Xinlong,Zhang, Heng,Lei, Aiwen
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supporting information
p. 10524 - 10527
(2015/06/25)
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- Ligand controlled orthogonal base-assisted direct C-H bond arylation in oxa(thia)zole-4-carboxylate series. New insights in nCMD mechanism
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Alkyl- and arylphosphines have been screened in competitive C2-H/C5-H direct phenylation of oxa(thia)zole-4-carboxylates using Cs2CO 3 and Rb2CO3 carbonate bases. nCMD-based C2-H selective direct phenylation was
- Théveau, Laure,Querolle, Olivier,Dupas, Georges,Hoarau, Christophe
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supporting information
p. 4375 - 4380
(2013/06/27)
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- Mechanism selection for regiocontrol in base-assisted, palladium-catalysed direct C-H coupling with halides: First approach for oxazole- and thiazole-4-carboxylates
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Both base-assisted non-concerted metallation-deprotonation (nCMD) and concerted metallation-deprotonation (CMD) have been identified as two potent operating mechanisms in palladium-catalysed direct C-H coupling of oxazole and thiazole-4-carboxylate esters
- Théveau, Laure,Verrier, Cécile,Lassalas, Pierrik,Martin, Thibaut,Dupas, Georges,Querolle, Olivier,Van Hijfte, Luc,Marsais, Francis,Hoarau, Christophe
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supporting information; experimental part
p. 14450 - 14463
(2012/01/15)
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- Carbonates: Eco-friendly solvents for palladium-catalysed direct arylation of heteroaromatics
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The palladium-catalysed direct 2-, 4- or 5-arylation of a wide range of heteroaromatics with aryl halides proceed in moderate to good yields using the eco-friendly solvents carbonates. The best yields were obtained using benzoxazole or thiazole derivatives. The arylation of furan, thiophene, pyrrole, imidazole or isoxazole derivatives was found to require a more elevated reaction temperature. The Royal Society of Chemistry 2010.
- Dong, Jia Jia,Roger, Julien,Verrier, Cecile,Martin, Thibaut,Le Goff, Ronan,Hoarau, Christophe,Doucet, Henri
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experimental part
p. 2053 - 2063
(2011/02/25)
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- Regioselective palladium-catalyzed phenylation of ethyl 4-oxazolecarboxylate
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The efficient and regioselective palladium-catalyzed C-2 arylation of ethyl 4-oxazolecarboxylate 1 with phenyliodide is described. The different parameters (solvent, base, ligand and catalyst) for the optimal conditions of this arylation process have been
- Hoarau, Christophe,De Kerdaniel, Alexis Du Fou,Bracq, Nicolas,Grandclaudon, Pierre,Couture, Axel,Marsais, Francis
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p. 8573 - 8577
(2007/10/03)
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- 2,6-Substituted chroman derivatives useful as beta-3 adrenoreceptor agonists
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This invention relates to novel 2,6-substituted chroman derivatives which are useful in the treatment of beta-3 adrenoreceptor-mediated conditions.
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- Di-substituted aminomethyl-chroman derivative beta-3 adrenoreceptor agonists
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This invention is related to novel di-substituted aminomethyl chroman derivatives which are useful in the treatment of beta-3 receptor-mediated conditions.
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- Benzofuran and dihydrobenzofuran derivatives useful as beta-3 adrenoreceptor agonists
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This invention relates to novel benzofuran and dihydrobenzofuran compounds, pharmaceutical compositions containing such compounds, and methods of treating beta-3 adrenoreceptor-mediated conditions with such compositions.
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Page/Page column 35
(2010/01/31)
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- COMPOUNDS FOR TREATING AND PREVENTING COGNITIVE DISEASES AND DEPRESSION AND METHODS OF MAKING SAME
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Ethylenediamine monoamides of the formula R--CO--NH--CH2 --CH2 --NH2. wherein R is one of groups in which R1 is phenyl monohalophenyl, monolower-alkylphenyl, monolower-alkoxypheynl, monotrifluoromethylphenyl, monocyanophenyl or monoaryl-lower-alkoxyphenyl, dihalophenyl, furyl, thienyl or monohalothienyl, R2 is hydrogen, halogen or amino, R3, R5 and R7 each are phenyl, monohalophenyl, dihalophenyl, thienyl, furyl or monohalofuryl, R4 and R6 each are hydrogen or amino and R8 is hydrogen or lower-alkyl, as well as their pharmaceutically usable acid addition salts are disclosed. The compounds have monoamine oxidase inhibiting properties with low toxicity and are useful for the treatment of depressive states and cognitive disorders
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- DIMETHYLALUMINIUM METHANESELENOLATE - A USEFUL REAGENT FOR THE PREPARATION OF SELENOESTERS. A NEW FRIEDEL-CRAFTS ACYLATION PROCEDURE PROMOTED BY Cu(I)
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The preparation of a new aluminium reagent, dimethylaluminium methaneselenolate (Me2AlSeMe) is described.The reactivity of this aluminium reagent toward a variety of organic substrates has been studied.Me2AlSeMe will convert O-alkyl esters to selenoesters in high yield.These selenoesters function as extremely reactive acyl transfer agents and are converted to acids, esters, and amides on reaction with water, alcohols or amines in the presence of a selenophilic metal cation.The selenoesters will, moreover, acylate reactive arenes and heterocyclic compounds when cuprous triflate is employed as the selenophilic metal cation.This latter transformation constitutes a new transition metal promoted variant of the Friedel-Crafts acylation reaction.
- Kozikowski, Alan P.,Ames, Anthony
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p. 4821 - 4834
(2007/10/02)
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