19832-78-1Relevant articles and documents
Dimethyl Sulfoxide Serves as a Dual Synthon: Construction of 5-Methyl Pyrimidine Derivatives via Four Component Oxidative Annulation
Xu, Cheng,Jiang, Shi-Fen,Wen, Xiao-Hui,Zhang, Qin,Zhou, Zhi-Wen,Wu, Yan-Dong,Jia, Feng-Cheng,Wu, An-Xin
, p. 2267 - 2271 (2018)
An efficient potassium persulfate mediated four component reaction for the construction of 5-methyl pyrimidine derivatives has been established from readily available methyl ketones, amidine hydrochlorides and dimethyl sulfoxide. This transformation featu
Enantioselective Copper-Catalyzed Electrophilic Sulfenylation of Cyclic Imino Esters
Chen, Zhiwei,Lin, Huaxin,Han, Jian,Fang, Dongmei,Wang, Min,Liao, Jian
supporting information, p. 9146 - 9150 (2021/11/30)
Herein we report an enantioselective sulfenylation of cyclic imino esters with the efficient and versatile sulfenylation reagent S-alkyl 4-methylbenzenesulfonothioates. By utilizing the Cu/tBu-Phosferrox catalytic system, we can assemble diverse S-alkyl groups into the cyclic imino esters under mild conditions in good yields and with excellent enantioselectivities. Remarkably, this method demonstrates a high tolerance of diverse functional groups and proves to be applicable in the late-stage functionalization of pharmaceuticals.
Design and synthesis of Mannich base-type derivatives containing imidazole and benzimidazole as lead compounds for drug discovery in Chagas Disease
Atherton, Richard L.,Kelly, John M.,Olmo, Francisco,Sanz-Serrano, Julen,Alcolea, Verónica,Beltran-Hortelano, Iván,Pérez-Silanes, Silvia,Rubio-Hernández, Mercedes
, (2021/07/14)
The protozoan parasite Trypanosoma cruzi is the causative agent of Chagas disease, the most important parasitic infection in Latin America. The only treatments currently available are nitro-derivative drugs that are characterised by high toxicity and limited efficacy. Therefore, there is an urgent need for more effective, less toxic therapeutic agents. We have previously identified the potential for Mannich base derivatives as novel inhibitors of this parasite. To further explore this family of compounds, we synthesised a panel of 69 new analogues, based on multi-parametric structure-activity relationships, which allowed optimization of both anti-parasitic activity, physicochemical parameters and ADME properties. Additionally, we optimized our in vitro screening approaches against all three developmental forms of the parasite, allowing us to discard the least effective and trypanostatic derivatives at an early stage. We ultimately identified derivative 3c, which demonstrated excellent trypanocidal properties, and a synergistic mode of action against trypomastigotes in combination with the reference drug benznidazole. Both its druggability and low-cost production make this derivative a promising candidate for the preclinical, in vivo assays of the Chagas disease drug-discovery pipeline.
Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures
Delost, Michael D.,Njardarson, Jon T.
supporting information, p. 6121 - 6125 (2021/08/16)
We report mild new annulation approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes via Darzens inspired protocols. The products of these anionic annulations, rarely studied previously, possess attractive features rendering them valuable building blocks for synthesis platforms. In this study, trisubstituted acetophenone nucleophiles bearing SCF3 and bromine substituents in their α position were shown to undergo [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.
Palladium-catalyzed regioselective synthesis of B(4,5)-or B(4)-substituted: O-carboranes containing α,β-unsaturated carbonyls
Li, Jiaoyi,Lu, Jian,Tian, Song,Wang, Qian,Zhang, Chuyi,Zhang, Jianwei,Zhou, Ling
supporting information, p. 4723 - 4727 (2020/07/13)
With the help of a carboxylic acid directing group, Pd-catalyzed regioselective synthesis of B(4,5)-or B(4)-substituted o-carboranes containing α,β-unsaturated carbonyls has been reported. The-COOH, removed during the course of the reaction, is responsible for controlling the regioselectivity. The desired products could be obtained in moderate to good yields.
A silver-catalyzed radical ring-opening reaction of cyclopropanols with sulfonyl oxime ethers
Wang, Xin,Zeng, Xiaobao,Zhang, Yanan,Zhao, Yu,Zhu, Li
supporting information, p. 3734 - 3739 (2020/06/03)
A silver-catalyzed ring-opening reaction of cyclopropanols with sulfonyl oxime ethers has been developed. The protocol was conducted under mild reaction conditions to provide a series of ?-keto oxime ethers with moderate to good yields. The reaction proceeded in a stereoselective manner for CF3-containing oxime ethers to provide a single stereoisomer, while an inseparableEandZmixture was obtained for CN-containing oxime ethers. Mechanistic studies indicate that the reaction proceededviaa radical mechanism.
PROCESS FOR THE DIRECT ALPHA-METHYLENATION OF KETONES
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Page/Page column 16; 17, (2020/06/10)
The invention relates to a process for preparing an α-methylene ketone comprising the step of reacting a ketone with formaldehyde in the presence of a catalyst which is an organic compound comprising at least one acid function or the corresponding salt, ester or amide thereof and at least one amine function or the corresponding ammonium salt, or a zwitterion thereof.
Asymmetric "clip-Cycle" Synthesis of Pyrrolidines and Spiropyrrolidines
Maddocks, Christopher J.,Ermanis, Kristaps,Clarke, Paul A.
supporting information, p. 8116 - 8121 (2020/11/02)
The development of an asymmetric "clip-cycle"synthesis of 2,2- and 3,3-disubstituted pyrrolidines and spiropyrrolidines, which are increasingly important scaffolds in drug discovery programs, is reported. Cbz-protected bis-homoallylic amines were activate
Copper-Catalyzed Asymmetric Hydrosilylation of β-Nitroethyl Aryl Ketones
Zeng, Weijun,Tan, Xuefeng,Yu, Yang,Chen, Gen-Qiang,Zhang, Xumu
supporting information, p. 858 - 862 (2020/01/31)
A copper-catalyzed asymmetric hydrosilylation of β-nitroethyl aryl ketones has been disclosed, and the corresponding chiral alcohols could be obtained in high yields (up to 99% yield) and excellent enantioselectivities (up to 96% ee). Moreover, the reaction worked well on a gram scale with 0.3 mol % of ligand loading, indicating that our protocol has potential applications in the synthesis of important pharmaceuticals such as Tranylcypromine and Ticagrelor.
Synthesis of novel multi-functionalized pyrrolidines by [3 + 2] dipolar cycloaddition of azomethine ylides and vinyl ketones
Pe?i?, Marko S.,Bugarinovi?, Jovana P.,Mini?, Aleksandra,Ili? Komatina, Danijela,Pejovi?, Anka,?mit, Biljana,Stevanovi?, Dragana,Damljanovi?, Ivan
, p. 663 - 679 (2019/03/11)
Abstract: An efficient and easy synthetic route to substituted pyrrolidine derivatives has been established through [3 + 2] dipolar cycloaddition of vinyl ketones and azomethine ylides. The reactions proceed smoothly, under mild conditions, affording mode
