32337-46-5Relevant academic research and scientific papers
Preparation and biological evaluation of new antimicrotubule agents: Modification of the imidazolidin-2-one moiety of phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonates
Gagné-Boulet, Mathieu,Bouzriba, Chahrazed,Chavez Alvarez, Atziri Corin,Fortin, Sébastien
, p. 187 - 196 (2021/10/19)
We prepared and biologically evaluated 32 novel molecules named phenyl 4-(dioxoimidazolidin-1-yl)benzenesulfonates (PID-SOs) and ethyl 2-(3-(4-(phenoxysulfonyl)phenyl)ureido)acetates (EPA-SOs). The antiproliferative activity of PID-SOs and EPA-SOs was ass
Aryl and heteroaryl nosylates as stable and cheap partners for Suzuki-Miyaura cross-coupling reactions
Dikova, Anna,Cheval, Nicolas P.,Blanc, Aurélien,Weibel, Jean-Marc,Pale, Patrick
, p. 1960 - 1968 (2016/04/05)
Aryl and heteroaryl para-nitrophenylsulfonates (nosylates) have been successfully engaged for the first time in Suzuki-Miyaura cross-coupling reactions with various aryl or vinylboronic acids (48-98%, 12 examples). The best catalyst/ligand combination have been determined to be 2 mol % of palladium acetate (Pd(OAc)2) and 4 mol % of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (XPhos) using K3PO4 as base, in tetrahydrofuran at 80 °C. These new reaction conditions notably provide a direct and very efficient access to the natural alkaloid dubamine.
One-pot tandem reactions for direct conversion of thiols and disulfides to sulfonic esters, alcohols to bis(indolyl)methanes and synthesis of pyrroles catalyzed by N-chloro reagents
Veisi, Hojat,Ataee, Meral,Fatolahi, Leila,Lotfi, Shahram
, p. 111 - 117 (2013/07/26)
A convenient synthesis of sulfonic esters from thiols and disulfides has been described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with Chloramin-T, tetra-butylammonium chloride (t-Bu4NCl) and water. The sulfonyl chlorides are then further allowed to react with phenol derivatives in the same reaction vessel. Also, a facile synthesis of bis(indolyl)methanes from alcohols using TCCA/KBr/wet-SiO2, and N-substituted pyrroles by reaction of hexane-2,5-dione with primary amines has been accomplished under mild condition with excellent yields.
One-pot tandem reactions for direct conversion of thiols and disulfides to sulfonic esters, and Paal-Knorr synthesis of pyrrole derivatives catalyzed by TCCA
Hemmati, Saba,Mojtahedi, Mohammad Majid,Abaee, Mohammad Saeed,Vafajoo, Zahra,Saremi, Shokufe Ghahri,Noroozi, Mohammad,Sedrpoushan, Alireza,Ataee, Meral
, p. 347 - 357 (2013/09/23)
A convenient synthesis of sulfonic esters from thiols and disulfides is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with trichloroisocyanuric acid (TCCA), tetra-butylammonium chloride (t-Bu4NCl), and water. The sulfonyl chlorides are then further allowed to react with phenol derivatives in the same reaction vessel. Also, a facile synthesis of N-substituted pyrroles by the reaction of hexane-2,5-dione with primary amines has been accomplished using TCCA as a catalyst under mild condition with excellent yields.
Synthesis of sulfonamides and sulfonic esters via reaction of amines and phenols with thiols using H2O2-POCl3 system
Bahrami, Kiumars,Khodaei, Mohammad M.,Abbasi, Jamshid
supporting information; experimental part, p. 5095 - 5101 (2012/07/28)
Phosphorus oxychloride efficiently promoted the synthesis of sulfonamides and sulfonic esters from thiols with hydrogen peroxide in the presence of Amberlite IRA-400 (OH-). This method has been applied to a variety of substrates including nucleophilic and sterically hindered amines, and also phenols with excellent yields of sulfonamides and sulfonic esters. In most cases these reactions are highly selective, simple, and clean, affording products in excellent yields and high purity.
A new preparative method of aryl sulfonate esters by using cyclic organobismuth reagents
Sakurai, Naoto,Mukaiyama, Teruaki
, p. 771 - 790 (2008/09/18)
A new method for the preparation of aryl sulfonate esters by using a cyclic pentavalent bismuth is described. Aryl sulfonate esters are formed in good to high yields by treating 10-arylphenothiabismine 5,5-dioxides, m-chloroperoxybenzoicacid (m-CPBA)and various sulfonic acids in dichloromethane.
Competitive Reaction Pathways in the Nucleophilic Substitution Reactions of Aryl Benzenesulfonates with Benzylamines in Acetonitrile
Choi, Jin Heui,Lee, Byung Choon,Lee, Hai Whang,Lee, Ikchoon
, p. 1277 - 1281 (2007/10/03)
The reactions of aryl benzenesulfonates (YC6H4SO2OC6H4Z) with benzylamines (XC6H4CH2NH2) in acetonitrile at 65.0 deg C have been studied. The reactons proceed competitevely by S-O (kS-O) and C-O (kC-O) bond scission, but the former provides the major reaction pathway. On the basis of analysis of the Hammet and Broensted coefficients together with the cross-interaction constants ρXY, ρYZ, and ρXZ, stepwise mechanisms are proposed in which the S-O bond cleavage proceeds by rate-limiting formation of a trigonal-bipyramidal pentacoordinate (TBP-5C) intermediate, whereas the C-O bond scission takes place by rate-limiting expulsion of the sulfonate anion (YC6H4SO3-) from a Meisenheimer-type complex.
Reactivity of sterically hindered aromatic sulfonic acid derivatives: VIII. * General mathematical model for catalytic sulfonylation of phenol
Rubleva,Maksimenko
, p. 1298 - 1300 (2007/10/03)
A general mathematical model is proposed for interpretation and prediction of the reactivity of sterically hindered arenesulfonyl chlorides in the catalytic sulfonylation of phenol. Some specific features of transition states in the catalytic and noncatal
Sulfonyl esters. 2. CS cleavage in some substitution reactions of nitrobenzensulfonates
Baum, James Clayton,Bolhassan, Jimat,Langler, Richard Francis,Pujol, Paul Joseph,Raheja, Raj Kumar
, p. 1450 - 1455 (2007/10/02)
An attempt to explore aromatic sulfonate esters as agents for the condensation of alcohols with mercaptans revealed an unusual process for sulfonate esters: CS bond rupture.Two mechanistic possibilities for CS bond rupture are explored: (i) radical anion intermediacy via singlet electron transfer and (ii) nucleophilic aromatic substitution.Both experiments and molecular orbital computations are presented to support the conclusion that nucleophilic aromatic substitutions are occuring.
Retardation of Hydrolysis of Aryl Arenesulphonate Esters by Quinuclidine through Complex Formation
Suh, Junghun,Suh,, Myung Koo,Cho, Seung Ho
, p. 685 - 688 (2007/10/02)
The hydrolysis of aryl arenesulphonate esters is considerably retarded upon the addition of quinuclidine (Quin).Kinetic and spectral data indicate that the protonated form of Quin forms non-covalent complexes with the sulphonate esters and that the comple
