135822-89-8Relevant academic research and scientific papers
Efficient and convenient preparation of N-tosylimines catalyzed by indium trichloride
Deng, Gui Sheng,Zou, Jing Yuan,Sun, Teng Fei
, p. 511 - 514 (2011)
A new method for preparation of N-tosylimines by InCl3-mediated condensation of aldehydes with p-toluenesulfonamide in refluxing benzene is reported. The procedure is lauded by its simplicity, mild reaction conditions, excellent yields and adap
Efficient and convenient procedure for preparation of N-sulfonylimines catalyzed by montmorillonite K-10
Jin, Tong-Shou,Yu, Mi-Jun,Liu, Li-Bin,Zhao, Ying,Li, Tong-Shuang
, p. 2339 - 2344 (2006)
A general and practical chemical route to the synthesis of N-sulfonylimines using montmorillonite K-10 as the catalyst is described. This method provides several advantages such as operational simplicity, short reaction time, using of inexpensive materials, noncorrosivity, lack of pollution, and high yields. Copyright Taylor & Francis Group, LLC.
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.
Synthesis of Benzyl Amines via Copper-Catalyzed Enantioselective Aza-Friedel-Crafts Addition of Phenols to N -Sulfonyl Aldimines
Shikora, Jonathan M.,Chemler, Sherry R.
supporting information, p. 2133 - 2137 (2018/04/30)
A new copper-catalyzed enantioselective aza-Freidel-Crafts reaction between phenols and N-sulfonyl aldimines that provides chiral secondary benzylamines in good to excellent yields and excellent enantioselectivities (up to 99% ee) is disclosed. In particular, excellent scope with alkylimines was observed for the first time. The synthetic utility of the products was demonstrated in the first enantioselective synthesis of a dual orexin receptor antagonist, a compound that contains an amine-bearing stereocenter adjacent to a bis-ortho-functionalized arene.
Formation of: N -sulfonyl imines from iminoiodinanes by iodine-promoted, N-centered radical sulfonamidation of aldehydes
Hopkins, Megan D.,Scott, Kristina A.,Demier, Brettany C.,Morgan, Heather R.,Macgruder, Jesse A.,Lamar, Angus A.
, p. 9209 - 9216 (2017/11/14)
A mild and operationally convenient formation of synthetically valuable N-sulfonyl imines from a range of aryl aldehydes by reaction with iminoiodinanes (PhINZ) and I2 has been developed. According to mechanistic experiments described within, the reaction is speculated to proceed through an unconventional light-promoted, N-centered radical (NCR) pathway involving a N,N-diiodosulfonamide reactive species. This method not only provides a new pathway toward the production of activated imines, but also serves as an example of a non-traditional means of carbonyl activation via an NCR species.
Development and Pharmacological Characterization of Selective Blockers of 2-Arachidonoyl Glycerol Degradation with Efficacy in Rodent Models of Multiple Sclerosis and Pain
Brindisi, Margherita,Maramai, Samuele,Gemma, Sandra,Brogi, Simone,Grillo, Alessandro,Di Cesare Mannelli, Lorenzo,Gabellieri, Emanuele,Lamponi, Stefania,Saponara, Simona,Gorelli, Beatrice,Tedesco, Daniele,Bonfiglio, Tommaso,Landry, Christophe,Jung, Kwang-Mook,Armirotti, Andrea,Luongo, Livio,Ligresti, Alessia,Piscitelli, Fabiana,Bertucci, Carlo,Dehouck, Marie-Pierre,Campiani, Giuseppe,Maione, Sabatino,Ghelardini, Carla,Pittaluga, Anna,Piomelli, Daniele,Di Marzo, Vincenzo,Butini, Stefania
, p. 2612 - 2632 (2016/04/10)
We report the discovery of compound 4a, a potent β-lactam-based monoacylglycerol lipase (MGL) inhibitor characterized by an irreversible and stereoselective mechanism of action, high membrane permeability, high brain penetration evaluated using a human in vitro blood-brain barrier model, high selectivity in binding and affinity-based proteomic profiling assays, and low in vitro toxicity. Mode-of-action studies demonstrate that 4a, by blocking MGL, increases 2-arachidonoylglycerol and behaves as a cannabinoid (CB1/CB2) receptor indirect agonist. Administration of 4a in mice suffering from experimental autoimmune encephalitis ameliorates the severity of the clinical symptoms in a CB1/CB2-dependent manner. Moreover, 4a produced analgesic effects in a rodent model of acute inflammatory pain, which was antagonized by CB1 and CB2 receptor antagonists/inverse agonists. 4a also relieves the neuropathic hypersensitivity induced by oxaliplatin. Given these evidence, 4a, as MGL selective inhibitor, could represent a valuable lead for the future development of therapeutic options for multiple sclerosis and chronic pain.
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
Assembly of homoallylamine derivatives through iron-catalyzed three-component sulfonamidoallylation reaction
Fan, Xiaohui,Zhu, Hong-Bo,Lv, Hao,Guo, Kun,Guan, Yong-Hong,Cui, Xiao-Meng,An, Bin,Pu, Yan-Ling
, p. 588 - 592 (2015/09/01)
An efficient FeCl3-catalyzed three-component reaction between aldehydes, sulfonamides and allylsilanes has been achieved, which provides a convenient, atom-economic and green way to construct homoallylamine derivatives. In addition, this reaction exhibits excellent syn stereoselectivity with γ-substituted allylsilanes. A practical three-component cascade process to homoallylamine derivatives is reported, which uses cheap and environmentally benign FeCl3 as catalyst and shows excellent syn stereoselectivity with γ-substituted allylsilanes.
Diastereoselective synthesis of pyrrolidine derivatives via a one-pot nitro-Mannich/hydroamination cascade using base and gold catalysis
?uri?, Andrej,Barber, David M.,Sanganee, Hitesh J.,Dixon, Darren J.
supporting information, p. 2777 - 2779 (2013/04/23)
An efficient one-pot nitro-Mannich/hydroamination cascade reaction for the synthesis of substituted pyrrolidines bearing three stereocentres is reported. Proceeding under the control of a combination of base and gold(i) catalysts, the cascade reaction aff
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.
