649-15-0Relevant academic research and scientific papers
Synthesis of Ferrocenesulfonyl Chloride: Key Intermediate toward Ferrocenesulfonamides
Erb, William,Wen, Min,Roisnel, Thierry,Mongin, Florence
, p. 2612 - 2620 (2021/05/06)
Ferrocenesulfonyl chloride is the key intermediate in the synthesis of ferrocenesulfonamides, a family of underexplored derivatives. A one-pot synthesis of this compound, able to easily deliver multigram quantities of product, is reported. An original protocol for the synthesis of ferrocenesulfonamides is described along with highlighting the reactivity difference between arene and ferrocenesulfonyl chlorides. Finally, an example of diastereoselective deprotolithiation of chiral ferrocenesulfonamides is described.
Recurrent Approximation of Retention Parameters of N-Substituted p-Toluenesulfonamides in Reversed-Phase High Performance Liquid Chromatography for Revealing the Formation of Their Hydrates
Kornilova, T. A.,Nikitina, D. A.,Zenkevich, I. G.
, p. 1931 - 1941 (2021/09/15)
Abstract: Recurrent approximation of retention times in reversed-phase high performance liquid chromatography (RP-HPLC), tR(C + ΔC) = atR(C) + b, where C is the acetonitrile concentration in the eluent, and ΔC is the constant “step” of its variation, for six specially synthesized N-substituted p-toluenesulfonamides confirmed the presence of anomalies previously revealed for some complex polyfunctional organic compounds. The reason for these anomalies is the presence of sulfonamide –SO2–NH fragments in the molecules, which leads to hydration of sorbates in aqueous solutions, or, more precisely, to a change in the ratio of their non-hydrated and hydrated forms because of a shift in the equilibrium Х + Н2О $$ rightleftarrows $$ Х·Н2О (*) as a result of a change in the eluent composition. The same effect is indicated by the strong antibatic dependence of the retention indices RI(C) of all sulfonamides under study; the coefficients dRI/dC vary from –1.9 to –4.0, these values being much higher in magnitude than for compounds that do not form hydrates. Further independent evidence in favor of the transformation of sorbates due to variation of the eluent composition is the dependence of the relative absorbance Arel = A(254)/A(220) on the acetonitrile content in the eluent. This suggests changes in the chemical nature of chromophores in sulfonamide molecules depending on the equilibrium state (*).
Debenzylative Sulfonylation of Tertiary Benzylamines Promoted by Visible Light
Fu, Ying,Wu, Qing-Kui,Du, Zhengyin
supporting information, p. 1896 - 1900 (2021/04/06)
An efficient, general, inexpensive, and environmentally friendly photosynthesis of sulfonamides via visible light promoted debenzylative sulfonylation of tertiary benzylamines is described. Compared to the traditional S?N coupling reactions, which are promoted by oxidative C?N bond cleavage of symmetrical tertiary alkylamines, this strategy provides a selective C?N bond cleavage protocol and avoids the use of transition-metal, explosive oxidants, and ligands.
Synthesis method of aryl tertiary sulfonamide compounds promoted by visible light
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Paragraph 0019-0020, (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.
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.
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.
KCC-1 aminopropyl-functionalized supported on iron oxide magnetic nanoparticles as a novel magnetic nanocatalyst for the green and efficient synthesis of sulfonamide derivatives
Azizi, Sajjad,Shadjou, Nasrin,Hasanzadeh, Mohammad
, (2019/11/22)
A new magnetic nanocatalyst (Fe3O4@KCC-1-npr-NH2) was synthesized directly through the reaction of Fe3O4@KCC-1 with (3-aminopropyl) triethoxysilane (APTES) using a hydrothermal protocol. Prepared nanocomposite was used as a magnetically reusable nanocatalyst for an efficient synthesis of a broad range of sulfonamide derivatives in water as a green solvent at room temperature and the products are collected by filtration with excellent yields (85–97%). The nanocatalyst could be remarkably recovered and reused after ten times without any significant decrease in activity. This mild and simple synthesis method offers some advantages including short reaction time, high yield and simple work-up procedure.
Synthesis method of aryl tertiary sulfonamide compound
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Paragraph 0026; 0027, (2019/10/01)
The invention provides a synthesis method of an aryl tertiary sulfonamide compound. In an aprotic solvent, with aryl sulfonyl chloride and a N,N-disubstituted-4-oxopiperidine quaternary ammonium saltcompound as raw materials and N-methylmorpholine as alka
Double C-N bond cleavages of: N-alkyl 4-oxopiperidinium salts: Access to unsymmetrical tertiary sulfonamides
Fu, Ying,Li, Ming-Peng,Shi, Chun-Zhao,Li, Fang-Rong,Du, Zhengyin,Huo, Congde
supporting information, p. 10172 - 10177 (2019/12/26)
In this paper, regiospecific, double intraannular C-N bond cleavages of N-alkyl 4-oxopiperidinium salts are presented. The reaction sequence involves a charge-transfer complex, in situ formed between sulfonyl chloride and N-methylmorpholine, which induces S-Cl bond homolysis of sulfonyl chloride, yielding a reactive sulfonyl radical that further induces the double C-N bond cleavages of N-alkyl 4-oxopiperidinium salt. The secondary amine thus produced was trapped by sulfonyl chloride to yield the desired sulfonamide product. The key feature of this protocol is that two intraannular C-N bonds of the 4-oxopiperidine ring are cleaved in one step under metal- A nd oxidant-free conditions.
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.
supporting information, 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.
