13053-89-9Relevant academic research and scientific papers
Blue Fluorescence from BF2 Complexes of N,O-Benzamide Ligands: Synthesis, Structure, and Photophysical Properties
Yamaji, Minoru,Kato, Shin-Ichiro,Tomonari, Kazuhiro,Mamiya, Michitaka,Goto, Kenta,Okamoto, Hideki,Nakamura, Yosuke,Tani, Fumito
, p. 12514 - 12519 (2017)
Small molecules having intense luminescence properties are required to promote biological and organic material applications. We prepared five types of benzamides having pyridine, pyridazine, pyrazine, and pyrimidine rings and successfully converted them i
A practical and sustainable protocol for direct amidation of unactivated esters under transition-metal-free and solvent-free conditions
Chen, Cheng,Cheng, Hua,Du, Min-Chen,Qian, Liang,Qin, Xin,Sang, Wei,Yao, Wei-Zhong,Yuan, Ye,Zhang, Rui
supporting information, p. 3972 - 3982 (2021/06/17)
In this paper, a NaOtBu-mediated synthesis approach was developed for direct amidation of unactivated esters with amines under transition-metal-free and solvent-free conditions, affording a series of amides in good to excellent yields at room temperature. In particular, an environmentally friendly and practical workup procedure, which circumvents the use of organic solvents and chromatography in most cases, was disclosed. Moreover, the gram-scale production of representative products3a,3wand3auwas efficiently realized by applying operationally simple, sustainable and practical procedures. Furthermore, this approach was also applicable to the synthesis of valuable molecules such as moclobemide (a powerful antidepressant), benodanil and fenfuram (two commercial agricultural fungicides). These results demonstrate that this protocol has the potential to streamline amide synthesis in industry. Meanwhile, quantitative green metrics of all the target products were evaluated, implying that the present protocol is advantageous over the reported ones in terms of environmental friendliness and sustainability. Finally, additional experiments and computational calculations were carried out to elucidate the mechanistic insight of this transformation, and one plausible mechanism was provided on the basis of these results and the related literature reports.
Copper-Catalyzed Tandem Reactions of 2-Amine-[1,3,5]triazines with Nitriles
Zhang, Li-Yu,Zhang, Chen,Wang, Tao,Shi, Yu-Long,Ban, Meng-Tao,Cui, Dong-Mei
, p. 536 - 543 (2019/01/24)
Copper-catalyzed intermolecular annulation of 2-amine-[1,3,5]triazines and aryl nitriles for the synthesis of [1,2,4]triazolo[1,5-a][1,3,5]triazines via N-C bond formation and oxidative N-N coupling [oxidative 3 + 2 cyclization] is presented. A wide range of aryl nitriles, including electron-rich benzonitriles, electron-poor benzonitriles, 2-cyanothiophene, and 4-cyanopyridine, were all functionalized with 2-amine-[1,3,5]triazines. Furthermore, amidation of 2-amine-[1,3,5]triazines via Cu-catalyzed C-CN bond cleavage of phenylacetonitriles is also demonstrated. The reaction occurred in moderate to satisfactory yields and tolerated alkyl- or aryl-substituted 2-amine-[1,3,5]triazines. Aniline, aminopyridine, and aminopyrimidine also afforded the desired products.
Solvent- and transition metal-free amide synthesis from phenyl esters and aryl amines
Rzhevskiy, Sergey A.,Ageshina, Alexandra A.,Chesnokov, Gleb A.,Gribanov, Pavel S.,Topchiy, Maxim A.,Nechaev, Mikhail S.,Asachenko, Andrey F.
, p. 1536 - 1540 (2019/01/24)
A general, economical, and environmentally friendly method of amide synthesis from phenyl esters and aryl amines was developed. This new method has significant advantages compared to previously reported palladium-catalyzed approaches. The reaction is performed transition metal- and solvent-free, using a cheap and environmentally benign base, NaH. This approach enabled us to obtain target amides in high yields with high atom economy.
Synthesis method of N-heterocyclic acylamide derivative
-
Paragraph 0066; 0067; 0068, (2019/01/14)
The invention discloses a synthesis method of an N-heterocyclic acylamide derivative. A reaction general formula is as shown in the specification. According to the synthesis method, an imidazo heterocyclic amine compound I is taken as a raw material; unde
Ce(III)-catalyzed highly efficient synthesis of pyridyl benzamides from aminopyridines and nitroolefins without external oxidants
Chen, Zhengwang,Wen, Xiaowei,Qian, Yiping,Liang, Pei,Liu, Botao,Ye, Min
supporting information, p. 1247 - 1251 (2018/03/06)
An efficient synthesis of a variety of pyridyl benzamides from 2-aminopyridines and nitroolefins is described. This rare-earth-metal-catalyzed reaction provides the corresponding products with broad substrate scope in moderate to excellent yields, in the absence of additives and external oxidants. Water is used as the source of the carbonyl oxygen atom in pyridyl benzamides. Furthermore, 2-substituted oxazolo[4,5-b]pyridines are formed in good yields under the standard conditions when 2-aminopyridin-3-ols are used as the substrates.
N-Methylamino Pyrimidyl Amides (MAPA): Highly Reactive, Electronically-Activated Amides in Catalytic N-C(O) Cleavage
Meng, Guangrong,Lalancette, Roger,Szostak, Roman,Szostak, Michal
supporting information, p. 4656 - 4659 (2017/09/12)
Despite recent progress in catalytic cross-coupling technologies, the direct activation of N-alkyl-N-aryl amides has been a challenging transformation. Here, we report the first Suzuki cross-coupling of N-methylamino pyrimidyl amides (MAPA) enabled by the controlled nN → πAr conjugation and the resulting remodeling of the partial double bond character of the amide bond. The new mode of amide activation is suitable for generating acyl-metal intermediates from unactivated primary and secondary amides.
An efficient, eco-friendly and sustainable tandem oxidative amidation of alcohols with amines catalyzed by heteropolyanion-based ionic liquids via a bifunctional catalysis process
Fu, Renzhong,Yang, Yang,Feng, Wei,Ge, Qiuxia,Feng, Yan,Zeng, Xiaojun,Chai, Wen,Yi, Jun,Yuan, Rongxin
, p. 8319 - 8326 (2016/12/02)
An efficient, eco-friendly and sustainable method for the tandem oxidative amidation of alcohols with amines has been reported. Using heteropolyanion-based ionic liquids as the catalyst and tert-butyl hydroperoxide as the oxidant, this amidation reaction is operationally straightforward and provides a series of primary, secondary and tertiary amides derivatives in moderate to good yields. Solvent-free media, microwave-promoted conditions and reusability of catalysts are the main highlights. Further, the proposed bifunctional catalysis mechanistic pathway has been briefly investigated in this report.
Microwave-assisted heteropolyanion-based ionic liquid promoted sustainable protocol to N-heteroaryl amides via N-directing dual catalyzed oxidative amidation of aldehydes
Fu, Renzhong,Yang, Yang,Jin, Weihua,Gu, Hui,Zeng, Xiaojun,Chai, Wen,Ma, Yunsheng,Wang, Quan,Yi, Jun,Yuan, Rongxin
, p. 107699 - 107707 (2016/11/29)
A sustainable procedure for the synthesis of N-heteroaryl amides directly from oxidative amidation of aldehydes catalyzed by heteropolyanion-based ionic liquids under microwave-promoted conditions has been reported. The transformation has proven to tolerate a wide range of aldehydes and amino heterocycles with different functional groups. Moderate to excellent yields, solvent-free media, operational simplicity and reusability of catalysts are the main highlights. Furthermore, the proposed N-directing dual-catalysis mechanistic pathway was briefly investigated in this report.
Practical preparation of challenging amides from non-nucleophilic amines and esters under flow conditions
Vrijdag, Johannes L.,Delgado, Francisca,Alonso, Nerea,De Borggraeve, Wim M.,Prez-Macias, Natalia,Alczar, Jesus
supporting information, p. 15094 - 15097 (2014/12/11)
A fast and efficient protocol for the formation of amides from low nucleophilic amines and esters in flow is described. Products were obtained in good to excellent yields and with the advantage of simultaneous mixing of all reagents at once, avoiding steps for intermediate formation. The protocol is also suitable to be combined with ester synthesis, resulting in the preparation of amides in-line from haloarenes. This journal is
