36176-90-6Relevant academic research and scientific papers
Facile synthesis, antimicrobial and antiviral evaluation of novel substituted phenyl 1,3-thiazolidin-4-one sulfonyl derivatives
Mandal, Milan Kumar,Ghosh, Swagatika,Naesens, Lieve,Bhat, Hans Raj,Singh, Udaya Pratap
, (2021/07/17)
A series of novel substituted phenyl 1, 3-thiazolidin-4-one sulfonyl derivatives 5 (a-t) were synthesized and screened for their in-vitro anti-microbial and anti-viral activity. The result of the anti-microbial assay demonstrated compounds 5d, 5f, 5g, 5h,
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.
Accelerated Reactivity Mechanism and Interpretable Machine Learning Model of N-Sulfonylimines toward Fast Multicomponent Reactions
Jethava, Krupal P.,Fine, Jonathan,Chen, Yingqi,Hossain, Ahad,Chopra, Gaurav
supporting information, p. 8480 - 8486 (2020/11/18)
We introduce chemical reactivity flowcharts to help chemists interpret reaction outcomes using statistically robust machine learning models trained on a small number of reactions. We developed fast N-sulfonylimine multicomponent reactions for understanding reactivity and to generate training data. Accelerated reactivity mechanisms were investigated using density functional theory. Intuitive chemical features learned by the model accurately predicted heterogeneous reactivity of N-sulfonylimine with different carboxylic acids. Validation of the predictions shows that reaction outcome interpretation is useful for human chemists.
The diastereoselective synthesis of 2,3-diaryl-3-cyano-substituted pyrrolidines via the MgI2 mediated ring expansion of aryl cyclopropyl nitriles
Stead, Darren
supporting information, (2020/09/04)
The MgI2 mediated reaction of aryl substituted cyclopropyl nitriles with tosyl aldimines to give 2,3-diaryl-3-cyano-substituted pyrrolidines has been demonstrated. In all cases, the trans-diastereoisomer was determined to be the major product.
Strategic vinyl sulfone nucleophile β-substitution significantly impacts selectivity in Vinylogous Darzens and aza-Darzens reactions
Delost, Michael D.,Njardarson, Jon T.
supporting information, p. 6917 - 6921 (2020/09/12)
Vinylogous Darzens and aza-Darzens reactions employing a benzothiophene 1,1-dioxide nucleophile are reported. These new [2 + 1] annulation reactions, which proceed under mild reaction conditions, are γ-selective, affording trans-epoxides selectively and favoring trans-aziridines. The reactions are base-dependent, with KOtBu and Cs2CO3 being optimal for aldehyde and imine annulations, respectively. Comparison of the benzothiophene nucleophile to its acyclic counterpart reveals superior performance in the case of aldehydes, while the outcome varies depending on the sulfonamide imine used.
Iron-based nanomaterials used as magnetic mesoporous nanocomposites to catalyze the preparation of N-sulfonylimines
Ashouri, Akram,Samadi, Saadi,Nasiri, Behzad,Bahrami, Zohre
, p. 549 - 556 (2019/08/01)
A new magnetic nanocatalyzed synthetic method for the synthesis of aldimines was evidenced. The reaction was carried out in a Schlenk tube under reflux conditions using various solvents and different nanomaterials as catalysts. In these reactions, an exce
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.
Ruthenium-Catalyzed Synthesis of Isoindolinones via Amide-Directed Addition of Aromatic C-H Bonds to Aldimines
Miura, Hiroki,Kimura, Yuriko,Terajima, Sachie,Shishido, Tetsuya
supporting information, p. 2807 - 2811 (2019/02/01)
Ruthenium-catalyzed addition of aromatic C-H bonds to aldimines is described. [RuCl2(p-cymene)]2 functions as an efficient catalyst to promote the coupling of aryl amides with aldimines in the presence of a catalytic amount of base to give the corresponding isoindolinone derivatives. The nature of the substituent at the N-atom of the amides is crucial for the efficient conversion of the substrates, and a p-toluenesulfonyl group is the functionality of choice. A variety of amides and aldimines participated in the present Ru-catalyzed reaction to furnish the corresponding isoindolinones in moderate to high yield.
Enantioselective Aza-Reformatsky Reaction with Ketimines
Maestro, Aitor,Martinez De Marigorta, Edorta,Palacios, Francisco,Vicario, Javier
supporting information, p. 9473 - 9477 (2019/11/28)
Here, an enantioselective aza-Reformatsky reaction using acyclic ketimine substrates is presented. Using α-phosphorated ketimines as electrophilic substrates and a simple BINOL-derived ligand, phosphorated analogues of aspartic acid holding chiral tetrasubstituted carbons are efficiently obtained with excellent enantioselectivity through an asymmetric organocatalytic Reformatsky-type reaction. The phosphorated analogues of aspartic acid have been used for the synthesis of phosphorus-containing enantiopure tetrasubstituted β-lactams.
Practical N-hydroxyphthalimide-mediated oxidation of sulfonamides to N-sulfonylimines
Wang, Jian,Yi, Wen-Jing
, (2019/11/02)
A new method to prepare sulfonylimines through the oxidation of sulfonamides mediated by N-hydroxyphthalimide under mild conditions has been developed. Compared to reported oxidation methods, broader substrates scope and milder conditions were achieved in
