87751-37-9Relevant academic research and scientific papers
Synthesis of Diversely Substituted Imidazolidines via [3+2] Cycloaddition of 1,3,5-Triazinanes with Donor-Acceptor Aziridines and Their Anti-Tumor Activity
Shi, Zhichao,Fan, Tingting,Zhang, Xun,Zhan, Feng,Wang, Zhe,Zhao, Lei,Lin, Jin-Shun,Jiang, Yuyang
supporting information, p. 2619 - 2624 (2021/04/05)
A Y(OTf)3-catalyzed [3+2] cycloaddition of 1,3,5-triazinanes with donor-acceptor aziridines has been developed, accessing diversely substituted imidazolidines high efficiency. Mechanistic investigations support the formation of imidazolidines through an SN1-like pathway. Furthermore, these imidazolidines exhibit promising anti-tumor activity against a series of human cancer cell lines. (Figure presented.).
Catalytic Asymmetric Hydroacyloxylation/Ring-Opening Reaction of Ynamides, Acids, and Aziridines
Li, Xiangqiang,Zeng, Hongkun,Lin, Lili,Feng, Xiaoming
supporting information, p. 2954 - 2958 (2021/05/05)
A highly enantioselective three-component reaction of ynamides with carboxylic acids and 2,2′-diester aziridines has been realized by using a chiral N,N′-dioxide/Ho(OTf)3 complex as a Lewis acid catalyst. The process includes the formation of an α-acyloxyenamide intermediate through the addition of carboxylic acids to ynamides and the following enantioselective nucleophilic addition to in-situ-generated azomethine ylides induced by the chiral catalyst. A range of amino acyloxyenamides are delivered in moderate to good yields with good ee values. In addition, a possible catalytic cycle with a transition model is proposed to elucidate the reaction mechanism.
Silica-supported zinc chloride (ZnCl2/SiO2)-induced efficient protocol for the synthesis of N-sulfonyl imines and 2-Arylbenzothiazole
Soliman, Hanan A.,El-Shahat, Mahmoud,Soliman, Abdel-Ghany
, p. 584 - 591 (2019/07/31)
A straightforward strategy for the synthesis of N-sulfonyl imine derivatives from sulfonamides and aryl aldehydes utilizing Silica-supported zinc chloride (ZnCl2/SiO2, silzic) as a catalyst under solvent-free conditions has been developed. 2-Arylbenzothiazole derivatives were also synthesized by the reaction of 2-aminothiophenol with aryl aldehydes under the same conditions. This procedure has advantages of high yields, mild reaction condition, simple procedure, low cost, and simplicity of workup. The catalyst has the same efficiency on its reuse up to three times.
Sulfinate-Organocatalyzed (3+2) Annulation Reaction of Propargyl or Allenyl Sulfones with Activated Imines
Martzel, Thomas,Lohier, Jean-Fran?ois,Gaumont, Annie-Claude,Brière, Jean-Fran?ois,Perrio, Stéphane
supporting information, p. 5069 - 5073 (2018/09/14)
An operationally simple methodology for the synthesis of 4-sulfonyl-3-pyrrolines is described using a propargylic sulfone and N-sulfonyl imines as substrates. This annulation process is initiated by an arenesulfinate organocatalyst, which allows a smooth isomerization of the alkynyl precursor into the corresponding allene, followed by the generation of a highly reactive allyl sulfone anion. An asymmetric version involving an unprecedented enantiopure sulfinate–ammonium cooperative ion pair (PhSO2– R4N+*) was investigated. A proof-of-concept, with enantiomeric excesses of up to 41 %, was obtained according to a preliminary screening of commercially available chiral phase-transfer catalysts.
Visible-light, iodine-promoted formation of n-sulfonyl imines and n-alkylsulfonamides from aldehydes and hypervalent iodine reagents
Hopkins, Megan D,Brandeburg, Zachary C.,Hanson, Andrew J.,Lamar, Angus A
, (2018/08/04)
Alternative synthetic methodology for the direct installation of sulfonamide functionality is a highly desirable goal within the domain of drug discovery and development. The formation of synthetically valuable N-sulfonyl imines from a range of aldehydes,
Synthesis of 3-(Arylsulfonyl)-3-pyrrolines from Allenyl Sulfonamides by Silver Ion Catalysis
Tata, Rama Rao,Fu, Chencheng,Kelley, Steven P.,Harmata, Michael
supporting information, p. 5723 - 5726 (2018/09/21)
Treatment of allenyl sulfonamides with catalytic amounts of silver fluoride in acetonitrile at reflux afforded the corresponding 3-sulfonyl-3-pyrrolines in excellent yields by intramolecular hydroamination via a 5-endo-trig cyclization. The starting allenyl sulfonamides were prepared by lithiation of allenic sulfones and trapping with various N-sulfonylimines.
Nitroxyl-Radical-Catalyzed Oxidative Coupling of Amides with Silylated Nucleophiles through N-Halogenation
Moriyama, Katsuhiko,Kuramochi, Masako,Fujii, Kozo,Morita, Tsuyoshi,Togo, Hideo
supporting information, p. 14546 - 14551 (2016/11/23)
A nitroxyl-radical-catalyzed oxidative coupling reaction between amines with an N-protecting electron-withdrawing group (EWG) and silylated nucleophiles was developed to furnish coupling products in high yields, thus opening up new frontiers in organocatalyzed reactions. This reaction proceeded through the activation of N-halogenated amides by a nitroxyl-radical catalyst, followed by carbon–carbon coupling with silylated nucleophiles. Studies of the reaction mechanism indicated that the nitroxyl radical activates N-halogenated amides, which are generated from N-EWG-protected amides and a halogenation reagent, to give the corresponding imines.
Synthesis of N-Sulfonyl Arylaldimines Developed by Retesting an Old Process
Huang, Dayun,Wang, Xuesong,Wang, Xingyong,Chen, Wenwen,Wang, Xinyan,Hu, Yuefei
supporting information, p. 604 - 607 (2016/02/18)
By simply heating the mixture of an arylaldehyde and a sulfonylisocyanate in a solvent or in neat form under catalyst- and additive-free conditions, the desired N-sulfonylimine was produced with the release of carbon dioxide. The method is characterized b
Hydrocyanation of sulfonylimines using potassium hexacyanoferrate(II) as an eco-friendly cyanide source
Li, Zheng,Li, Rongzhi,Zheng, Huanhuan,Wen, Fei,Li, Hongbo,Yin, Junjun,Yang, Jingya
, p. 1739 - 1743 (2014/01/06)
An efficient and eco-friendly method for hydrocyanation of sulfonylimines via one-pot two-step procedure using potassium hexacyanoferrate(II) as a cyanide source, benzoyl chloride as a promoter, and potassium carbonate as a base is described. This protocol has the features of using nontoxic, nonvolatile and inexpensive cyanide source, high yield, and simple work-up procedure.
