10546-70-0Relevant articles and documents
Aminolysis of 2,2,2-Trichloro-1-arylethanones in Aprotic Solvents
Druzian, Janice,Zucco, Cesar,Rezende, Marcos Caroli,Nome, Faruk
, p. 4767 - 4771 (1989)
The kinetics of the reaction of the title substrate with various alkylamines was studied in n-heptane, dichloromethane, dioxane, tetrahydrofuran, and acetonitrile.The reaction was third-order in amine when the solvent was n-heptane or dichloromethane.In the other solvents a second-order dependence on was observed.The fourth-order rate constants for the reaction of n-butylamine with various 2,2,2-trichloro-1-arylethanones in dichloromethane yielded a ρ value of 3.0.In all solvents the observed rate constans decreased with a temperature increase.Two mechanistic possibilities were suggested, the first one in solvents of low donicity, involving a T0 intermediate formed in a concerted process with the participation of an amine dimer; and the second one, a stepwise process in more basic solvents which takes place via a T+/- intermediate.Base-catalyzed collapse of the tetrahedral intermediates is the rate-determining step in both pathways.
The direct amidation of α-diketones with amines via TBHP-promoted oxidative cleavage of C(sp2)-C(sp2) bonds
Zhao, Qiong,Li, Hongji,Wang, Lei
, p. 6772 - 6779 (2013)
A novel and efficient direct amidation of α-diketones with amines via TBHP-promoted oxidative cleavage of C(sp2)-C(sp2) bonds has been developed. The strategy provides an alternative approach to amides under metal-free conditions.
Ester aminolysis catalyzed by nucleosides in a nonpolar medium
Melander, Christian,Horne, David A.
, p. 8344 - 8346 (1996)
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Electrophilic Activation of Amides for the Preparation of Polysubstituted Pyrimidines
Stopka, Tobias,Adler, Pauline,Hagn, Gerhard,Zhang, Haoqi,Tona, Veronica,Maulide, Nuno
, p. 194 - 202 (2019)
In this article we describe the straightforward synthesis of polysubstituted pyrimidines by electrophilic activation of secondary amides in the presence of alkynes. An unusual mechanistic detour leading to pyridine derivatives as products is also presente
Amidoethylation of Anthracene Hydride by N-Aroylaziridines: Inner-sphere Single Electron Transfer (SET) and Radical Coupling confirmed
Lin,Stamm
, p. 646 - 647 (1998)
Regioselectivity (near 1:1) of substitutive ring opening of 1-benzoyl-2-methylaziridine by anthracene hydride is incompatible with common nucleophilic attack and thus confirms the radical coupling path.
The Mechanisms of Photochemical Reactions of o-Sulfobenzoic Imides
Ono, Isao,Sato, Shohei,Fukuda, Kiyoshi,Inayoshi, Tomoko
, p. 2051 - 2055 (1997)
The photochemical processes of N-propyl-o-sulfobenzoic imide to the amides were investigated in ethanol and monocyclic aromatics, such as benzene, anisole, toluene, polymethylbenzenes, and benzonitrile. It was clarified that although both the S1 and T1 states took part in those photochemical reactions, the mechanisms were different in ethanol and those aromatics. The mechanism in ethanol is thought to involve hydrogen-atom abstraction from ethanol by a diradical formed after the extrusion of sulfur dioxide. The mechanism in aromatics involved an energy transfer from the singlet excited aromatic molecules to the sulfobenzoic imide and the addition of the resulting diradicals to the partner aromatics. Although the sulfobenzoic imide sensitized to a triplet state by acetophenone in benzene resulted as well in the formation of the arylated benzamide, this process was minor in comparison with the process via the S1 state. This was attributed to the triplet multiplicity of the diradical. The reactions of the sulfobenzoic imide with p-xylene and mesitylene were less predominant than those with toluene and anisole, which was attributable to a steric effect of plural methyl groups on the ring. The fact that no formation of the arylated benzamides took place in the case of benzonitrile could be explained by a strong inductitive effect of a cyano group of benzonitrile.
Linke
, p. 303 (1978)
One-pot synthesis of amides from carboxylic acids activated using thionyl chloride
Leggio,Belsito,De Luca,Di Gioia,Leotta,Romio,Siciliano,Liguori
, p. 34468 - 34475 (2016)
A one-pot synthesis of secondary and tertiary amides from carboxylic acids and amines by using SOCl2 has been developed. Also when sterically hindered amines were used as the starting materials, excellent yields of the corresponding amides were obtained. The amidation of N-protected α-amino acids with secondary amines proceeds effectively with good yields. The process works well also in the presence of acid sensitive groups and occurs with almost complete retention of stereochemical integrity of chiral substrates. This protocol could be extended to industrial large-scale production processes.
A study on reactions of an alkynylsilane with oxone-KX (X = Cl, Br, I) and its one-pot transformation into an amide/ester
Sriramoju, Vinodkumar,Jillella, Raveendra,Kurva, Srinivas,Madabhushi, Sridhar
, p. 560 - 562 (2017)
Oxyhalogenation reactions of a variety of alkynylsilanes were studied using oxone as mild oxidant and KCl, KBr, and KI as halogen sources. In this study, reaction of an alkynylsilane with oxone-KX (X = Cl or Br) produced trichloromethyl/tribromomethyl ketones inhigh yields. Under similar conditions, however, reactions of alkynylsilanes with oxone-KI were found to give exclusively 1,2,2-triiodovinyl derivatives in high yields. In this study, new methods were deveoped for effcient one-pot tranformation of alkynylsilanes into amides and esters by reaction with amines and alcohols respectively via trihalomethyl ketone.
Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides
Qu, Erdong,Li, Shangzhang,Bai, Jin,Zheng, Yan,Li, Wanfang
supporting information, p. 58 - 63 (2021/12/27)
Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.
Cobalt-catalyzed alkene hydrogenation by reductive turnover
van der Puyl, Vincent,McCourt, Ruairi O.,Shenvi, Ryan A.
supporting information, (2021/04/19)
Earth abundant metal catalysts hold advantages in cost, environmental burden and chemoselectivity over precious metal catalysts. Differences in reactivity for a given metal center result from ligand field strength, which can promote reaction through either open- or closed-shell carbon intermediates. Herein we report a simple protocol for cobalt-catalyzed alkene reduction. Instead of using an oxidative turnover mechanism that requires stoichiometric hydride, we find a reductive turnover mechanism that requires stoichiometric proton. The reaction mechanism appears to involve coordination and hydrocobaltation of terminal alkenes.
Visible-light-induced direct construction of amide bond from carboxylic acids with amines in aqueous solution
Wang, Jin,Hou, Huiqing,Hu, Yongzhi,Lin, Jin,Wu, Min,Zheng, Zhiqiang,Xu, Xiuzhi
supporting information, (2021/02/09)
A novel visible-light-promoted N-acylation for the synthesis of amides from easily available carboxylic acids with amines in the presence of I2 within 2.5 h in aqueous solution has been developed. Using sunlight as the visible light source greatly reduces the cost of experiments and produces almost no toxic effects. Hence, this study provides an alternative catalytic system for the construction of a wide range of amides with readily available materials. Moreover, the strategy was successfully applied in the preparation of N-(3-(2,6-dimethoxyphenoxy)-7-nitroquinoxalin-2-yl)benzohydrazide, which displayed a signification anti-proliferation effect on A549, MCF-7 and HCT116 cell lines.
