5421-40-9Relevant academic research and scientific papers
Organocatalytic and enantioselective [4+2] cyclization between hydroxymaleimides and: Ortho -hydroxyphenyl para -quinone methide-selective preparation of chiral hemiketals
Xiang, Min,Li, Chen-Yi,Song, Xiang-Jia,Zou, Ying,Huang, Zhi-Cheng,Li, Xia,Tian, Fang,Wang, Li-Xin
supporting information, p. 14825 - 14828 (2020/12/07)
A cinchona alkaloid squaramide promoted enantioselective [4+2] cyclization between hydroxymaleimides and ortho-hydroxyphenyl p-QMs has been disclosed, and a wide range of chiral hemiketals containing chromane and succinimide frameworks with two adjacent quaternary stereogenic centers have been prepared for the first time with excellent results (up to 99% yield, up to 99?:?1 dr, up to >99% ee) under mild conditions. This journal is
Chemoselective α,β-Dehydrogenation of Saturated Amides
Teskey, Christopher J.,Adler, Pauline,Gon?alves, Carlos R.,Maulide, Nuno
supporting information, p. 447 - 451 (2019/01/04)
We report a method for the selective α,β-dehydrogenation of amides in the presence of other carbonyl moieties under mild conditions. Our strategy relies on electrophilic activation coupled to in situ selective selenium-mediated dehydrogenation. The α,β-unsaturated products were obtained in moderate to excellent yields, and their synthetic versatility was demonstrated by a range of transformations. Mechanistic experiments suggest formation of an electrophilic SeIV species.
Catalyst-Free Transamidation of Aromatic Amines with Formamide Derivatives and Tertiary Amides with Aliphatic Amines
Yin, Jiawen,Zhang, Jingyu,Cai, Changqun,Deng, Guo-Jun,Gong, Hang
supporting information, p. 387 - 392 (2019/01/11)
A simple catalyst- and promoter-free protocol has been developed for the transamidation of weakly nucleophilic aromatic amines with formamide derivatives and low-reactivity tertiary amides with aliphatic amines. This strategy is advantageous because no catalyst or promoters are needed, no additives are required, separation and purification is easy, and the reaction is scalable. Significantly, this strategy was further applied to synthesize several pharmaceutical molecules on a gram scale, and excellent yields were achieved.
A non-catalyst non-promoter under the conditions of amide derivatives of aromatic amine with transfers the amine reaction
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Paragraph 0095; 0096, (2019/03/28)
The present invention discloses a non-catalyst under the condition of non-accelerator [...] amide derivatives of aromatic amine with transfers the amine reaction, yield of synthetic N - aryl amide derivatives. The method has a wide range of the substrate, its raw materials and cheap and easy to obtain acylation reagent, the reaction yield is high, one-step reaction, low cost, high reaction selectivity, simple operation and the like. Adopting this method can be gram scale can realize the high yield of the synthesis of drug molecules. Therefore, the method in the N - aryl amide derivatives of synthesis application field has very good application prospect. The method overcomes the existing technologies such as the reaction reagent toxicity is large, the need to use different type catalyst, synthesis method and the cost is high, more reaction steps, more byproducts and the like.
Catalyst- and Supporting-Electrolyte-Free Electrosynthesis of Benzothiazoles and Thiazolopyridines in Continuous Flow
Folgueiras-Amador, Ana A.,Qian, Xiang-Yang,Xu, Hai-Chao,Wirth, Thomas
supporting information, p. 487 - 491 (2017/12/15)
A catalyst- and supporting electrolyte-free method for electrochemical dehydrogenative C?S bond formation in continuous flow has been developed. A broad range of N-arylthioamides have been converted to the corresponding benzothiazoles in good to excellent yields and with high current efficiencies. This transformation is achieved using only electricity and laboratory grade solvent, avoiding degassing or the use of inert atmosphere. This work highlights three advantages of electrochemistry in flow, which is (i) a supporting electrolyte-free reaction, (ii) an easy scale-up of the reaction without the need for a larger reactor and, (iii) the important and effective impact of having a good mixing of the reaction mixture, which can be achieved effectively with the use of flow systems. This clearly improves the reported methods for the synthesis of benzothiazoles.
Preparation method of amide compounds
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Paragraph 0041-0042, (2018/09/28)
The invention discloses a novel preparation method of amide compounds. According to the preparation method, perfluoroalkyl amide is taken as the raw material, a transition metal catalyst is adopted, perfluoroalkyl amide carries out reactions for a while in an organic aprotic solvent at a certain temperature, amide compounds can be obtained high selectively, and the yield is high. The preparation method has the advantages of low cost, high yield, and simple and convenient operation, and can be possibly applied to industrial production.
Organocatalytic Asymmetric Annulation between Hydroxymaleimides and Nitrosoarenes: Stereoselective Preparation of Chiral Quaternary N-Hydroxyindolines
Yang, Yu,Ren, Hong-Xia,Chen, Feng,Zhang, Zheng-Bing,Zou, Ying,Chen, Chao,Song, Xiang-Jia,Tian, Fang,Peng, Lin,Wang, Li-Xin
supporting information, p. 2805 - 2808 (2017/06/07)
An unusual and highly effective asymmetric annulation of nitrosoarenes with hydroxymaleimides catalyzed by a chiral bifunctional amine squaramide catalyst has been disclosed. A wide range of highly fused chiral N-hydroxyindolines with two consecutive quaternary stereocenters and multifunctional groups were directly and effectively prepared in excellent yields (up to >99%) with complete regioselective cyclization and excellent stereoselectivities (up to >99:1 dr and >99% ee). The efficiency and potentials of the new reaction and the target chiral entities were well demonstrated by delicate transformations into a series of new chiral indolines.
N-Acyl-N-(4-chlorophenyl)-4-nitrobenzenesulfonamides: Highly selective and efficient reagents for acylation of amines in water
Ebrahimi, Sara,Saiadi, Safoura,Dakhilpour, Simin,Mirsattari, Seyed Nezamoddin,Massah, Ahmad Reza
, p. 95 - 104 (2016/04/26)
A variety of N-acyl-N-(4-chlorophenyl)-4-nitrobenzenesulfonamides (1a-e) were synthesized in one pot from 4-chloroaniline under solvent-free conditions and have been developed as chemoselective N-acylation reagents. Selective protection of primary amines in the presence of secondary amines, acylation of aliphatic amines in the presence of aryl amines, and monofunctionalization of primary-secondary diamines as well as selective N-acylation of amino alcohols using these reagents are described. All of the acylation reactions were carried out in water as a green solvent. High stability and easy preparation of these acylating reagents are other advantages of this method.
Zirconium-catalyzed direct amide bond formation between carboxylic esters and amines
Lenstra, Danny C.,Nguyen, D. Thao,Mecinovi?, Jasmin
, p. 5547 - 5553 (2015/08/03)
Development of catalytic amide bond formation reactions from readily available starting materials remains a challenging task for modern organic chemistry. Herein, we report that unactivated carboxylic esters and amines react in the presence of 10 mol % of zirconocene dichloride (Cp2ZrCl2) in toluene at 110 °C to afford amides in very good to excellent conversions. The Zr-catalyzed reaction is amenable for the amidation of aliphatic and aromatic carboxylic esters with primary and secondary amines. The reaction proceeds with almost complete retention of configuration for chiral esters and chiral amines.
Hydrogen bond organocatalysis of benzotriazole in transamidation of carboxamides with amines
Nguyen, Thanh Binh,Ermolenko, Ludmila,Dau, Marie-Elise Tran Huu,Al-Mourabit, Ali
, p. 403 - 416 (2014/01/17)
A new method of transamidation of carboxamides with amines catalyzed by benzotriazole has been developed.
