605-85-6Relevant academic research and scientific papers
1,2-Aryl Migration Induced by Amide C?N Bond-Formation: Reaction of Alkyl Aryl Ketones with Primary Amines Towards α,α-Diaryl β,γ-Unsaturated γ-Lactams
Hu, Rong,Tao, Yigao,Zhang, Xiaofeng,Su, Weiping
supporting information, p. 8425 - 8430 (2021/03/16)
Rearrangement reactions incorporated into cascade reactions play an important role in rapidly increasing molecular complexity from readily available starting materials. Reported here is a Cu-catalyzed cascade reaction of α-(hetero)aryl-substituted alkyl (hetero)aryl ketones with primary amines that incorporates an unusual 1,2-aryl migration induced by amide C?N bond formation to produce a class of structurally novel α,α-diaryl β,γ-unsaturated γ-lactams in generally good-to-excellent yields. This cascade reaction has a broad substrate scope with respect to primary amines, allows a wide spectrum of (hetero)aryl groups to smoothly undergo 1,2-migration, and tolerates electronically diverse α-substituents on the (hetero)aryl ring of the ketones. Mechanistically, this 1,2-aryl migration may stem from the intramolecular amide C?N bond formation which induces nucleophilic migration of the aryl group from the acyl carbon center to the electrophilic carbon center that is conjugated with the resulting iminium moiety.
Palladium-catalyzed synthesis of α-aryl acetophenones from styryl ethers and aryl diazonium saltsviaregioselective Heck arylation at room temperature
Kandasamy, Jeyakumar,Lee, Yong Rok,Singh, Adesh Kumar,Venkatesh, Rapelly
supporting information, p. 7832 - 7837 (2021/09/28)
Preparation of α-aryl acetophenones from styryl ethers and aryldiazonium salts is described. The reaction is catalyzed by palladium acetate at room temperature in the absence of ligand and base. The developed method is highly attractive in terms of reaction conditions, substrate scope, functional group tolerance and yields. Synthetic applications of the present method are demonstrated by preparing α-aryl indoles and 3-aryl isocoumarin from styryl ethers.
An Oxidant- And Catalyst-Free Synthesis of Dibenzo[ a, c ]carbazoles via UV Light Irradiation of 2,3-Diphenyl-1 H -indoles
Hou, Rong,Kang, Yang,Liang, Yong,Min, Xiaoyan,Wang, Tao,Zhang, Zunting
, (2021/12/13)
An efficient methodology for the synthesis of dibenzo[a,c]- carbazoles via annulation of 2,3-diphenyl-1H-indoles in EtOH under UV light irradiation (λO = 365 nm) along with hydrogen evolution is described. This method exhibits the advantages of mild reaction conditions, no requirement of any oxidants and catalysts, and release of hydrogen as the only byproduct. Notably, the mechanism investigation confirms that the trans-4b,8a-dihydro-9H-dibenzo[a,c]carbazole intermediate could convert into cis-4b,8a-dihydro-9H-dibenzo[a,c]carbazole, which relies on the nitrogen atom of the indole ring. This is followed by intramolecular dehydrogenation which yields the dibenzo[a,c]carbazoles. 2021. Thieme. All rights reserved.
NCN-Pincer palladium complexes immobilized on MCM-41 molecular sieve: Application in Α-arylation reactions
Kai, Wang,Qian, Hua,Liu, Dabin,Ye, Zhiwen
, p. 85 - 91 (2018/11/21)
Aromatic para-functionalized NCN pincer compounds tethered to a triethoxysilane moiety through a carbamate linkage were immobilized on ordered MCM-41 molecular sieve using a grafting process. The acquired immobilized organometallic pincer complexes were synthesized in high yields with no complex degradation and characterized by IR sprctroscopy, elemental content analysis. Nitrogen physisorption, XRD and TEM revealed that the mesoporous structure was retained during the immobilization process. The hybrid materials were applied as Lewis acid catalysts in the α-arylation reaction between aryl ketones and aryl halides, with the yield up to 95%. The tendency to form mono- or di-arylated products was investigated and the catalyst could be easily recovered and reused in five runs without a significant loss in its activity.
Mn/Cu catalyzed addition of arylboronic acid to nitriles: Direct synthesis of arylketones
Moustafa, Dina,Sweet, Chelsea,Lim, Hyun,Calalpa, Brenda,Kaur, Parminder
, p. 3816 - 3820 (2018/09/18)
A direct and efficient synthesis of arylketones via arylboronic acid addition to nitriles in presence of inexpensive Mn/Cu catalytic system is reported. The use of non-precious Mn and Cu salts has been found to be highly advantageous both in terms of accessibility as well as cost effectiveness. A series of arylboronic acids as well as nitriles were used to synthesize a variety of symmetrical and unsymmetrical arylketones. Based on the literature studies, the reaction mechanism is anticipated to go through an aryl radical intermediate which reacted with the copper activated nitrile to give the desired arylketones after the hydrolysis of the imine intermediate.
Two-Step One-Pot Synthesis of Unsymmetrical (Hetero)Aryl 1,2-Diketones by Addition-Oxygenation of Potassium Aryltrifluoroborates to (Hetero)Arylacetonitriles
Kumar, Yogesh,Jaiswal, Yogesh,Kumar, Amit
, p. 494 - 505 (2018/02/09)
An efficient one-pot two-step procedure for the synthesis of unsymmetrical (hetero)aryl 1,2-diketones has been developed. The reaction proceeds through a palladium-catalyzed nucleophilic addition of potassium aryltrifluoroborates to aliphatic nitriles followed by a copper-catalyzed aerobic benzylic C–H oxygenation using molecular oxygen as a green oxidant. This represents the first example of the direct synthesis of unsymmetrical diaryl 1,2-diketones from arylacetonitriles. This method utilizes inexpensive, stable, nontoxic, and readily available starting materials, is highly effective in the presence of both electron-rich and electron-poor nitriles and aryltrifluoroborates, and tolerates a wide variety of functional groups. The synthetic utility of this transformation was shown by increasing the scale of the reaction and by carrying out the one-pot protocol for the preparation of quinoxaline and benzimidazole derivatives. A plausible reaction mechanism has also been proposed.
Base-mediated insertion reaction of alkynes into carbon-carbon σ-bonds of ethanones: synthesis of hydroxydienone and chromone derivatives
Zhang, Fangfang,Yao, Qiyi,Yuan, Yang,Xu, Murong,Kong, Lingkai,Li, Yanzhong
supporting information, p. 2497 - 2500 (2017/04/03)
Transition-metal free insertions of alkynes into carbon-carbon σ-bonds of ethanones have been reported. These tandem reactions offer an efficient synthesis of hydroxydienones and multi-substituted chromones. This is the first example of base-promoted insertion reactions of isolated carbon-carbon triple bonds into carbon-carbon σ-bonds with active methylene compounds bearing only one electron-withdrawing group.
New synthetic approaches towards analogues of bedaquiline
Priebbenow, Daniel L.,Barbaro, Lisa,Baell, Jonathan B.
supporting information, p. 9622 - 9628 (2016/10/25)
Multi-drug resistant tuberculosis (MDR-TB) is of growing global concern and threatens to undermine increasing efforts to control the worldwide spread of tuberculosis (TB). Bedaquiline has recently emerged as a new drug developed to specifically treat MDR-
X-ray structural and biological evaluation of a series of potent and highly selective inhibitors of human coronavirus papain-like proteases
Báez-Santos, Yahira M.,Barraza, Scott J.,Wilson, Michael W.,Agius, Michael P.,Mielech, Anna M.,Davis, Nicole M.,Baker, Susan C.,Larsen, Scott D.,Mesecar, Andrew D.
, p. 2393 - 2412 (2014/04/17)
Structure-guided design was used to generate a series of noncovalent inhibitors with nanomolar potency against the papain-like protease (PLpro) from the SARS coronavirus (CoV). A number of inhibitors exhibit antiviral activity against SARS-CoV infected Ve
Diarylated ethanones from Mo(CO)6-mediated and microwave-assisted palladium-catalysed carbonylative Negishi cross-couplings
Motwani, Hitesh V.,Larhed, Mats
supporting information, p. 4729 - 4733 (2013/08/23)
Two protocols for palladium-catalysed carbonylative Negishi cross-couplings were developed for aryl iodides and aryl bromides. The two main breakthroughs were that molybdenum hexacarbonyl [Mo(CO)6] could be used as a solid in situ source of CO, and that controlled microwave irraditaion could be used for heating. Consequently, the reactions were safe (in contrast to when CO gas was used) and fast (in comparison to when conventional heating was used). The carbonylative cross-coupling reactions were carried out using commercially available benzylzinc bromide in closed vials (90-120°C for 0.5-1 h) to give a set of diarylated ethanones, a common pharmacophore found in several pharmaceuticals, in moderate to high isolated yields (47-84 %). The mild three-component carbonylation protocol presented here is operationally simple, safe, and rapid, and the formation of the carbonylative Negishi cross-coupling product is favoured over the product of Negishi cross-coupling. Copyright
