34251-46-2Relevant academic research and scientific papers
Potent antagonists of the Kv1.5 potassium channel: Synthesis and evaluation of analogous N,N-diisopropyl-2-(pyridine-3-yl)acetamides
Nanda, Kausik K.,Brad Nolt,Cato, Matthew J.,Kane, Stefanie A.,Kiss, Laszlo,Spencer, Robert H.,Wang, Jixin,Lynch, Joseph J.,Regan, Christopher P.,Stump, Gary L.,Li, Bing,White, Rebecca,Yeh, Suzie,Bogusky, Michael J.,Bilodeau, Mark T.,Dinsmore, Christopher J.,Lindsley, Craig W.,Hartman, George D.,Wolkenberg, Scott E.,Wesley Trotter
, p. 5897 - 5901 (2006)
This letter describes the discovery of a novel series of potent Kv1.5 ion channel antagonists based on a diisopropyl amide scaffold. Structure-activity relationships of functionalized analogs are discussed. Key compound 1-(3-(diisopropylcarbamoyl)-2-pheny
Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates
Chattopadhyay, Buddhadeb,Hassan, Mirja Md Mahamudul,Hoque, Md Emdadul
supporting information, p. 5022 - 5037 (2021/05/04)
Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.
Preparation method of aryl acetamide compound
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Paragraph 0034-0040, (2020/12/08)
The invention discloses a preparation method of an aryl acetamide compound. The method comprises the following steps: adding a palladium catalyst, a ligand, benzyl formate, tertiary amine and trifluoroacetic anhydride into an organic solvent, performing reacting at 130 DEG C for 24 hours, and after the reaction is completed, carrying out after-treatment to obtain the aryl acetamide compound. The preparation method is easy to operate, the after-treatment is simple and convenient, reaction initial raw materials are cheap and easily available, benzyl formate is taken as both a carbon monoxide source and a reactant, tertiary amine is taken as an amine source, substrate designability is high, substrate functional group tolerance range is wide, and reaction efficiency is high. What is noteworthyis that C-N bonds of the tertiary amine are broken in the reaction, no extra oxidizing agent is needed, various aryl acetamide compounds can be synthesized according to actual needs, and practicability is high.
Formamide catalyzed activation of carboxylic acids-versatile and cost-efficient amidation and esterification
Huy, Peter H.,Mbouhom, Christelle
, p. 7399 - 7406 (2019/08/20)
A novel, broadly applicable method for amide C-N and ester C-O bond formation is presented based on formylpyrrolidine (FPyr) as a Lewis base catalyst. Herein, trichlorotriazine (TCT), which is the most cost-efficient reagent for OH-group activation, was employed in amounts of ≤40 mol% with respect to the starting material (100 mol%). The new approach is distinguished by excellent cost-efficiency, waste-balance (E-factor down to 3) and scalability (up to >80 g). Moreover, high levels of functional group compatibility, which includes acid-labile acetals and silyl ethers, are demonstrated and even peptide C-N bonds can be formed. In comparison to reported amidation procedures using TCT, yields are considerably improved (for instance from 26 to 91%) and esterification is facilitated for the first time in synthetically useful yields. These significant enhancements are rationalized by activation by means of acid chlorides instead of less electrophilic acid anhydride intermediates.
Phototriggered Active Alkyne Generation from Cyclopropenones with Visible Light-Responsive Photocatalysts
Mishiro, Kenji,Kimura, Takeshi,Furuyama, Taniyuki,Kunishima, Munetaka
supporting information, p. 4101 - 4105 (2019/06/17)
A photocatalytic active alkyne generation reaction was developed using cyclopropenone as a starting reagent. Visible light-responsive photocatalysts induced cyclopropenone decarbonylation. The resulting highly reactive alkyne could be used directly, witho
A Revised Mechanism for the Kinugasa Reaction
Malig, Thomas C.,Yu, Diana,Hein, Jason E.
supporting information, p. 9167 - 9173 (2018/07/15)
Detailed kinetic analysis for the Cu(I)-catalyzed Kinugasa reaction forming β-lactams has revealed an anomalous overall zero-order reaction profile, due to opposing positive and negative orders in nitrone and alkyne, respectively. Furthermore, the reaction displays a second-order dependence on the catalyst, confirming the critical involvement of a postulated bis-Cu complex. Finally, reaction progress analysis of multiple byproducts has allowed a new mechanism, involving a common ketene intermediate to be delineated. Our results demonstrate that β-lactam synthesis through the Kinugasa reaction proceeds via a cascade involving (3 + 2) cycloaddition, (3 + 2) cycloreversion, and finally (2 + 2) cycloaddition. Our new mechanistic understanding has resulted in optimized reaction conditions to dramatically improve the yield of the target β-lactams and provides the first consistent mechanistic model to account for the formation of all common byproducts of the Kinugasa reaction.
Phototriggered Dehydration Condensation Using an Aminocyclopropenone
Mishiro, Kenji,Yushima, Yuki,Kunishima, Munetaka
supporting information, p. 4912 - 4915 (2017/09/23)
A phototriggered dehydration condensation using an aminocyclopropenone has been developed. The UV irradiation of an aminocyclopropenone generated a highly reactive ynamine in situ and the dehydration condensation of a carboxylic acid and an amine coexisting in the reaction solution smoothly proceeded to afford an amide. This reaction is completely controllable by the ON/OFF states of a UV lamp.
Charge-Transfer Complex Promoted C-N Bond Activation for Ni-Catalyzed Carbonylation
Yu, Hui,Gao, Bao,Hu, Bin,Huang, Hanmin
supporting information, p. 3520 - 3523 (2017/07/17)
A new strategy was developed for activation of C-N bond via formation of an amine-I2 charge-transfer complex, which facilitates the inert C-N bond activation via oxidative addition with Ni(0). This strategy has been successfully applied in the Ni-catalyzed carbonylation of benzylamines via direct insertion of CO into the C-N bond, which provided a straightforward and rapid approach to arylacetamides in the presence of catalytic amounts of I2 and Ni catalyst. Mechanistic studies suggested that a benzyl radical generated via the oxidative addition was involved in the present reaction.
Synthesis of Unsymmetrical Diaryl Acetamides, Benzofurans, Benzophenones, and Xanthenes by Transition-Metal-Free Oxidative Cross-Coupling of sp3 and sp2 C-H Bonds
Rathore, Vandana,Sattar, Moh.,Kumar, Raushan,Kumar, Sangit
, p. 9206 - 9218 (2016/10/14)
A chemo- and regioselective intermolecular sp3 C-H and sp2 C-H coupling reaction for C-C bond formation is described to access unsymmetrical diaryl acetamides under TM-free conditions from sec- and tert-arylacetamides and nitroarenes using tert-butoxide base in DMSO at room temperature. The coupling partners with sensitive functionalities such as chloro, bromo, hydroxy, and cyano were also amenable to the developed reaction. Synthesized α-(2/4-nitroaryl) phenylacetamides have been transformed into biologically important benzofurans, xanthenes, diaryl indoles, and unsymmetrical benzophenones by novel routes without applying a transition metal. Overall, an economical, yet efficient, strategy has been devised to access unsymmetrical diarylacetamides with the possibility of their further elaboration into a variety of biologically important heterocycles. Mechanistic understanding suggests that the reaction proceeds by a nucleophilic addition of a phenylacetamide carbanion, which is generated in the presence of tert-butoxide base, to the para or ortho (if para is substituted) position of nitrobenzene. The formed α-(4-nitrocyclohexa-2,4-dien-1-yl) phenylacetamide anion intermediate oxidized by a basic solution of DMSO or atmospheric oxygen led to the desired sp3 C-H and sp2 C-H coupled α-(2/4-nitroaryl) phenylacetamides.
Direct amidation of carboxylic acids with tertiary amines: Amide formation over copper catalysts through C-N bond cleavage
Xiong, Biquan,Zhu, Longzhi,Feng, Xiaofeng,Lei, Jian,Chen, Tieqiao,Zhou, Yongbo,Han, Li-Biao,Au, Chak-Tong,Yin, Shuang-Feng
supporting information, p. 4244 - 4247 (2014/07/21)
A copper-catalyzed system for the amidation of carboxylic acids with tert-amines through C-N bond cleavage was developed. This protocol is practical and represents a simple way to produce functionalized amides from basic starting materials in moderate to good yields. A plausible mechanism is proposed for the reaction. Copyright
