80-17-1Relevant articles and documents
Investigation of spectroscopic, structural and non-linear optical properties of ethyl 3,5-dimethyl-4-[(benzenesulfonyl)-hydrazonoethyl]-1H-pyrrol- 2-carboxylate
Singh,Rawat, Poonam,Sahu, Sangeeta
, p. 123 - 133 (2013)
This paper describes the synthesis, spectroscopic 1H and 13C NMR, UV-Visible, FT-IR analysis, elemental analysis, structural evaluation and non-linear optical (NLO) properties of newly synthesized compound, ethyl 3,5-dimethyl-4-[(benzenesulfonyl)-hydrazonoethyl]-1H-pyrrol-2- carboxylate using experimental and quantum chemical techniques. FT-IR spectrum, electronic descriptors, molecular electrostatic potential surface (MEPS) and quantum theory of atoms in molecule (QTAIM) have been used to predict the sites and nature of interactions. A combined experimental and theoretical vibrational analysis identified red shifts in vNH and vCO as result of hydrogen bonding confirming formation of the dimer in the solid phase. The binding energy of dimer has been evaluated as 9.72 kcal/mol. The value of Gibbs free energy change (ΔG) shows that dimer formation is thermodynamically spontaneous. At room temperature, the equilibrium constant (Keq) for dimerization reaction is calculated to be 18.91 i.e. Keq a?‰
Complementary Site-Selective Sulfonylation of Aromatic Amines by Superacid Activation
Bourbon, Paul,Appert, Emeline,Martin-Mingot, Agnès,Michelet, Bastien,Thibaudeau, Sébastien
supporting information, p. 4115 - 4120 (2021/06/21)
Under superacidic conditions, aniline and indole derivatives are sulfonylated at low temperature with easy-to-access arenesulfonic acids or arenesulfonyl hydrazides. By modification of the functional-group directing effect through protonation, this method allows nonclassical site functionalization by overcoming the innate regioselectivity of electrophilic aromatic substitution. This superacid-mediated sulfonylation of arenes is complementary to existing methods and can be applied, through protection by protonation, to the late-stage site-selective functionalization of natural alkaloids and active pharmaceutical ingredients.
Electrochemical heterodifunctionalization of α-CF3alkenes to access α-trifluoromethyl-β-sulfonyl tertiary alcohols
Chen, Kai,Duan, Xin-Yu,Gao, Jie,Guan, Jian-Ping,Liu, Fang,Xiang, Hao-Yue,Xiao, Jun-An,Yang, Hua,Ye, Zhi-Peng
supporting information, p. 8969 - 8972 (2021/09/10)
An unprecedented electrochemical heterodifunctionalization of α-CF3alkenes with benzenesulfonyl hydrazides was accomplished in this work, wherein a β-sulfonyl and a α-hydroxyl group were simultaneously incorporated across the olefinic double bond in a single operation. Consequently, a series of potentially medicinally valuable and densely functionalized α-trifluoromethyl-β-sulfonyl tertiary alcohols were assembled under mild conditions. Electrochemically-driven oxidative 1,2-difunctionlization of electron-deficient alkenes well obviates the need for oxidizing reagents, thus rendering this protocol more eco-friendly.
Electrochemical fluorosulfonylation of styrenes
Jiang, Yi-Min,Wu, Shao-Fen,Yan, Hong,Ye, Ke-Yin,Yu, Yi,Yuan, Yaofeng
supporting information, p. 11481 - 11484 (2021/11/16)
An environmentally friendly and efficient electrochemical fluorosulfonylation of styrenes has been developed. With the use of sulfonylhydrazides and triethylamine trihydrofluoride, a diverse array of β-fluorosulfones could be readily obtained. This reaction features mild conditions and a broad substrate scope, which could also be conveniently extended to a gram-scale preparation.
Synthesis and hyperglycemic, biochemical and histopathological evaluation of novel sulfonylbiguanide and sulfonylurea derivatives as potent anti-diabetic agents
Basyouni, Wahid M.,Abbas, Samir Y.,El-Bayouki, Khairy A.M.,Younis, Eman A.,Ali, Sanaa A.,Aly, Hanan F.
, (2021/11/01)
New sulfonylbiguanide hydrochloride salts and sulfonylurea derivatives containing two sulfonyl groups were synthesized through the reaction of arylsulfonohydrazides with cyanoguanidine and p-tolylsulfonylisocyanate, respectively. Oral treatment of hyperglycemic rats with the synthesized sulfonylbiguanide derivatives 2 and sulfonylurea derivatives 3 revealed that sulfonylurea derivatives 3a and 3c possessed significant decrease of the elevated glucose in compression with the anti-diabetic standard drugs. Effects of the synthesized sulfonylurea derivatives 3a and 3c on the diabetic properties towards α-amylase, liver function enzyme levels (AST, ALT, ALP, TB and γ-GT), kidney functions (urea and creatinine), lipids profiles (TG, TL, TC and HDL-C) were studied. Also, the effect of sulfonylurea derivatives 3a and 3c as antioxidants (reduced glutathione and lipid peroxide) was evaluated. Histopathological examination of hepatic and pancreatic tissues was investigated. The obtained results suggested that the most potent sulfonylurea derivatives 3a and 3c might be possible used as novel diabetic inhibitor agents.
Dual Roles of Rongalite: Reductive Coupling Reaction to Construct Thiosulfonates Using Sulfonyl Hydrazides
Zhang, Guofu,Fan, Qiankun,Zhao, Yiyong,Wang, Huimin,Ding, Chengrong
supporting information, p. 81 - 85 (2020/11/03)
A tunable and practical transformation of structurally diverse sulfonyl hydrazides into thiosulfonates in the presence of Rongalite (NaHSO 2·CH 2O) was developed. Transition-metal-free conditions, operational simplicity, and readily available reagents are the striking features of this protocol. It is the first example for the synthesis of thiosulfonates using sulfonyl hydrazides with the assistance of reductant. Additionally, the mechanistic studies revealed that this transformation probably undergoes via a reducing-coupling pathway.
Iodine-Mediated Coupling of Cyclic Amines with Sulfonyl Hydrazides: an Efficient Synthesis of Vinyl Sulfone Derivatives
Rong, Xiaona,Guo, Jingwen,Hu, Zheqi,Huang, Lehao,Gu, Yugui,Cai, Yuepiao,Liang, Guang,Xia, Qinqin
supporting information, p. 701 - 708 (2020/12/30)
An efficient iodine-mediated coupling of cyclic amines with sulfonyl hydrazides is reported. This transformation opens a new route to the synthesis of vinyl sulfones derivatives, which is a common structural motif in natural products and pharmaceuticals. Tentative mechanistic studies suggest that this reaction is likely to involve a radical process.
NaHSO3-Mediated Direct Synthesis of Sulfinic Esters from Sulfonyl Hydrazides under Transition-Metal-Free Conditions
Zhang, Guofu,Fan, Qiankun,Wang, Huimin,Zhao, Yiyong,Ding, Chengrong
supporting information, p. 833 - 837 (2020/12/07)
We have developed a protocol for the NaHSO3-promoted esterification of sulfonyl hydrazides with alcohols for the synthesis of sulfinic esters. Various sulfonyl hydrazides could be converted to the corresponding sulfinic esters in good to high yields. The merits of this protocol include mild transition-metal-free reaction conditions, an inexpensive and available reagent, and operational simplicity. Controlled experiments reveal that this transformation probably undergoes via a radical pathway. (Figure presented.).
Palladium-Catalyzed Asymmetric Hydrosulfonylation of 1,3-Dienes with Sulfonyl Hydrazides
Li, Ming-Ming,Cheng, Lei,Xiao, Li-Jun,Xie, Jian-Hua,Zhou, Qi-Lin
supporting information, p. 2948 - 2951 (2020/12/15)
A highly enantio- and regioselective hydrosulfonylation of 1,3-dienes with sulfonyl hydrazides has been realized by using a palladium catalyst containing a monodentate chiral spiro phosphoramidite ligand. The reaction provided an efficient approach to synthetically useful chiral allylic sulfones. Mechanistic studies suggest that the reaction proceeds through the formation of an allyl hydrazine intermediate and subsequent rearrangement to the chiral allylic sulfone product. The transformation of the allyl hydrazine intermediate to the product is the enantioselectivity-determining step.
Photoredox/cobaloxime co-catalyzed allylation of amines and sulfonyl hydrazines with olefins to access α-allylic amines and allylic sulfones
Tong, Qing-Xiao,Xu, Hui,Zhang, Hong,Zhong, Jian-Ji
supporting information, p. 8227 - 8231 (2021/10/12)
Herein, we reported a dual-catalytic platform for the allylation of amines and sulfonyl hydrazines with olefins to selectively access α-allylic amines and allylic sulfones in good yields by combining photoredox catalysis and cobaloxime catalysis. This strategy avoided the use of a stoichiometric amount of terminal oxidant and the use of pre-functionalized allylic precursors, representing a green and ideal atom- & step-economical process. Good substrate scope and gram-scale synthesis demonstrated the utility of this protocol. Mechanistic studies revealed that a radical process is probably involved in this reaction.
