6435-78-5Relevant articles and documents
Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides
Chen, Rongxiang,Xu, Shaohong,Shen, Fumin,Xu, Canran,Wang, Kaikai,Wang, Zhanyong,Liu, Lantao
, (2021/09/20)
A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.
Method for preparing N-sulfonyl tetrahydropyrrole compound by using gold complex
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Paragraph 0054-0059, (2021/07/17)
The invention relates to a method for preparing an N-sulfonyl tetrahydropyrrole compound by using a gold complex, which comprises the following step of: reacting a sulfonamide compound and a tetrahydrofuran compound as raw materials with a gold complex containing an ortho-carborane Schiff base ligand as a catalyst at room temperature to obtain the N-sulfonyl tetrahydropyrrole compound. Compared with the prior art, the method has the advantages that the gold complex containing the ortho-carborane Schiff base ligand is adopted as the catalyst, the sulfonamide compound and the tetrahydrofuran compound can be catalyzed to react under the room temperature condition to prepare the N-sulfonyl tetrahydropyrrole compound, the usage amount of the catalyst is low, the reaction condition is mild, the reaction rate is high, the product yield is high, the substrate is high in universality, the raw materials are cheap and easy to obtain, and the method has a wide application prospect in industry.
Diastereoselective synthesis of conformationally restricted KOR agonists
Ilari, Denise,Maskri, Sarah,Schepmann, Dirk,K?hler, Jens,Daniliuc, Constantin G.,Koch, Oliver,Wünsch, Bernhard
, p. 4082 - 4099 (2021/05/19)
In order to analyze the bioactive conformation of flexible KOR agonists the ethylenediamine KOR pharmacophore was conformationally constrained by incorporation into a bicyclic system. For this purpose, 2-azabicyclo[3.2.1.]octan-7-amines were designed, synthesized and pharmacologically evaluated. The primary amine 14 as first key intermediate was prepared in a six-step synthesis starting with methyl cyclopent-3-enecarboxylate 9. Whereas phenylacetamides failed to provide bicyclic compounds, the intramolecular nucleophilic substitution of the sulfonamide 25 was initiated by deprotonation with NaH affording the bicyclic compound 26 in 72% yield. The three-step introduction of the pharmacophoric pyrrolidine ring started with nucleophilic substitution of exo-configured tosylate 26 with NaN3, which unexpectedly occurred under retention of configuration leading to exo-configured azide 31. The final KOR agonists 35 and 36 with exo-configured amino moieties were obtained by removal of the N-tosyl moiety of 33 and introduction of the second pharmacophoric element by acylation with dihalophenylacetyl chlorides. The KOR affinity of the pyrrolidine 35a is in the high nanomolar range (Ki = 862 nM). The low KOR affinity is explained by a non-appropriate dihedral angle of 137°/141° of the N(pyrrolidine)-C-C-N(acyl) system. As observed for stereoisomers of potent KOR agonists, phenylacetamide 35a and more importantly sulfonamides 33a and 33b show moderate affinity at σ1 receptors (Ki = 109-208 nM). This journal is
Synthesis method of aryl tertiary sulfonamide compounds promoted by visible light
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Paragraph 0021-0022, (2021/01/25)
The invention provides a synthesis method of aryl tertiary sulfonamide compounds promoted by visible light. In a non-protonic solvent, N-benzyl tertiary amine and arylsulfonyl chloride are used as rawmaterials, under the conditions of photosensitizer catalysis and illumination, a reaction is carried out for 1-4h at room temperature, and then separation and purification are carried out to obtain the product. The synthesis method of the aryl tertiary sulfonamide compound provided by the invention has the advantages of mild reaction conditions, simplicity and convenience in operation, short reaction time, no need of any transition metal catalysis and environmental friendliness.
NEW SELECTIVE MODULATORS OF INSECT NICOTINIC ACETYLCHOLINE RECEPTORS
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Page/Page column 19; 22, (2020/06/01)
The present invention relates to a compound having the following formula (I): wherein: - A is a (hetero)aryl radical comprising from 5 to 10 carbon atoms, possibly substituted by at least one substituent chosen from the group consisting of: halogen atoms, amino, azido, cyano, nitro, hydroxyl, formyl, carboxyl, amido, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, alkenyl groups, cycloalkenyl groups, and alkynyl groups, and - R is H, CN or CF3, or their pharmaceutically acceptable salts, racemates, diastereomers or enantiomers.
Synthesis of sulfonamides promoted by alkyl iodide via a hypervalent iodine intermediate
Zhou, Zhongshi,He, Xuehan
supporting information, p. 280 - 284 (2019/11/16)
A new method for the preparation of sulfonamides from sodium sulfinates and amines is developed. A stoichiometric amount of m-chloroperbenzoic acid as oxidant and a catalytic amount of 1-iodopropane provides the corresponding sulfonamides in good yields under mild reaction conditions. In this protocol, 1-iodopropane is first oxidized by m-chloroperbenzoic acid into the corresponding hypervalent iodine intermediate iodosylpropane, which is highly unstable and decomposes at once to form hypoiodous acid. Then, the following reaction of the generated active hypoiodous acid with sodium sulfinates and amines results in the corresponding sulfonamides.
Water soluble homogeneous catalysts that are recoverable by phase selectivity and host-guest interactions
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Page/Page column 2, (2020/08/30)
A chemical reaction is catalyzed in an organic solvent using a water soluble N-heterocyclic carbene homogeneous catalyst to form a reaction mixture. An aqueous phase in the reaction mixture. A solvent in which the catalyst is insoluble is added to the reaction mixture, causing the catalyst to migrate to the aqueous phase to form a catalyst-laden aqueous phase. The catalyst is extracted from the catalyst-laden aqueous phase.
Synthesis method of beta-aryl sulfonyl enamine compound
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Paragraph 0036-0039, (2020/05/29)
The invention belongs to the technical field of organic synthesis. The invention relates to the technical field of organic synthesis, in particular to a synthesis method of a beta-aryl sulfonyl enamine compound, which comprises the following steps: in an air environment, with a sodium benzenesulfinate derivative and tertiary amine as substrates, carrying out anodic oxidation coupling reaction in amixture of an electrolyte and a solvent to obtain the beta-aryl sulfonyl enamine compound. The synthesis method of the beta-aryl sulfonyl enamine compound provided by the invention is free of metal,oxidant and halogen, the whole synthesis process is harmless to the environment, and a variety of beta-aryl sulfonyl enamine compounds with satisfactory yield can be obtained.
TBAI-catalyzed selective synthesis of sulfonamides and β-aryl sulfonyl enamines: coupling of arenesulfonyl chlorides and sodium sulfinates with tert-amines
Jiang, Hongmei,Tang, Xiaoyue,Xu, Zhihui,Wang, Huixian,Han, Kang,Yang, Xiaolan,Zhou, Yuanyuan,Feng, Yong-Lai,Yu, Xian-Yong,Gui, Qingwen
, p. 2715 - 2720 (2019/03/12)
A simple, practical and metal-free method has been developed for the synthesis of sulfonamides and β-arylsulfonyl enamines via the selective cleavage of C-N and C-H bonds through the iodine-catalyzed oxidation of arenesulfonyl chlorides and sodium sulfinates with tert-amines. The method uses commercially available inexpensive catalysts and oxidants, and has a wide substrate scope and operational simplicity.
Hypervalent Iodine Mediated Sulfonamide Synthesis
Poeira, Diogo L.,Macara, Jo?o,Faustino, Hélio,Coelho, Jaime A. S.,Gois, Pedro M. P.,Marques, M. Manuel B.
, p. 2695 - 2701 (2019/04/08)
A new metal-free sulfonylation reaction is described. The method takes advantage of the Umpolung reactivity and group-transfer properties of iodine(III) compounds, combining hypervalent iodine reagents and sulfinate salts to deliver a clean and mild transfer of sulfonyl groups to amines and anilines. A total of 25 sulfonamides was synthesised in up to 99 % yield, even on gram-scale. The reaction mechanism was investigated by ESI-MS and DFT calculations.
