- Dual Roles of Rongalite: Reductive Coupling Reaction to Construct Thiosulfonates Using Sulfonyl Hydrazides
-
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.
- Zhang, Guofu,Fan, Qiankun,Zhao, Yiyong,Wang, Huimin,Ding, Chengrong
-
supporting information
p. 81 - 85
(2020/11/03)
-
- NaHSO3-Mediated Direct Synthesis of Sulfinic Esters from Sulfonyl Hydrazides under Transition-Metal-Free Conditions
-
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.).
- Zhang, Guofu,Fan, Qiankun,Wang, Huimin,Zhao, Yiyong,Ding, Chengrong
-
supporting information
p. 833 - 837
(2020/12/07)
-
- One-pot synthesis of sulfonylhydrazones from sulfonyl chloride, hydrazine hydrate and vinyl azide in water
-
A facile and eco-friendly protocol for the synthesis of sulfonylhydrazones from sulfonyl chlorides, hydrazine hydrate and vinyl azides was developed. The unique advantage of this approach is that desired products can be obtained efficiently in water, which meets the requirements of green chemistry and provides good perspectives for the sustainable production of new drug candidate. Also, this reaction proceeded in moderate to good yields with a wide tolerance of functional groups.
- Luo, Mengqiang,Wang, Hai,Ren, Xiaorong,Lu, Ruijuan,Qi, Chenze,Zhang, Yaohong,Shen, Runpu
-
p. 2713 - 2722
(2021/03/19)
-
- Synthesis of symmetrical / unsymmetrical thiosulfonates through the disproportionate coupling reaction of sulfonyl hydrazide mediated by phosphomolybdic acid
-
Phosphomolybdic acid (H3PMo12O40) is reported as a green low-cost catalyst for the synthesis of symmetrical / unsymmetrical thiosulfonates via the disproportionate coupling reaction of sulfonyl hydrazide. The attributes of this reported catalytic system include low catalyst loadings (1 mol%), efficient turnover, and high yields (up to 94%). Additionally, this reaction mechanism involves the formation of a thiyl radical and sulfonyl radical via sulfinyl radical disproportionation.
- Lv, Mengting,Liu, Yufeng,Li, Ke,Yang, Guoping
-
supporting information
(2021/01/21)
-
- Copper-Catalyzed Sulfonylation of Cyclobutanone Oxime Esters with Sulfonyl Hydrazides
-
A copper-catalyzed radical cross-coupling of cyclobutanone oxime esters with sulfonyl hydrazides has been developed. The copper-based catalytic system proved crucial for cleavage of the C-C bond of cyclobutanone oximes and for selective C-S bond-formation involving persistent sulfonyl-metal radical intermediates. This protocol is distinguished by the low-cost catalytic system, which does not require ligand, base, or toxic cyanide salt, and by the use of readily accessible starting materials, as well as broad substrate scope, providing an efficient approach to various diversely substituted cyano-containing sulfones.
- Dong, Bingbing,Lu, Jiansha,Bao, Honghao,Zhang, Yuanyuan,Liu, Yingguo,Leng, Yuting
-
supporting information
p. 3769 - 3776
(2021/07/14)
-
- Electrochemical fluorosulfonylation of styrenes
-
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.
- Jiang, Yi-Min,Wu, Shao-Fen,Yan, Hong,Ye, Ke-Yin,Yu, Yi,Yuan, Yaofeng
-
supporting information
p. 11481 - 11484
(2021/11/16)
-
- Heterogeneous copper-catalyzed synthesis of diaryl sulfones
-
A carbon-supported copper nanoparticle (Cu-NP) with high catalytic activity for the synthesis of diaryl sulfones is reported. For the first time, this Cu-NP is proved to be able to effectively promote the reaction of arylboronic acids and arylsulfonyl hydrazides to generate diaryl sulfones at room temperature. The reaction shows excellent substrate universality, and substrates with different substituents can undergo the reaction smoothly, leading to the desired products in good yields. The Cu-NP is found to be made of low valence Cu based on XRD. Hence, the reaction catalyzed by the Cu-NP is believed to involve a Cu-mediated organometallic cycle.
- Gong, Xinchi,Qu, Lingling,Shen, Zhengqi,Wang, Ganghu,Zhu, Chunyin
-
supporting information
p. 10662 - 10668
(2021/12/27)
-
- Electrochemically Induced Synthesis of Sulfonylated N-Unsubstituted Enamines from Vinyl Azides and Sulfonyl Hydrazides
-
Sulfonylated N-unsubstituted enamines were synthesized through a chain of chemical and electrochemical transformations via sulfonylation of vinyl azides. The disclosing of the N-unsubstituted enamines synthesis was based on a unique property of the azido group, which is its ability to eliminate the N2 molecule. Furthermore, a formal paradox is observed: A double bond reacts and a double bond is retained. Electrosynthesis proceeded in an undivided cell equipped with a graphite anode and a stainless steel cathode; NH4I was used as a supporting electrolyte.
- Mulina, Olga M.,Zhironkina, Nataliya V.,Paveliev, Stanislav A.,Demchuk, Dmitry V.,Terent'Ev, Alexander O.
-
supporting information
p. 1818 - 1824
(2020/03/04)
-
- A general and practical sulfonylation of benzylic ammonium salts with sulfonyl hydrazides for the synthesis of sulfones
-
A practical and efficient approach adopting transition-metal-free cross-coupling of sulfonyl hydrazides with benzyl ammonium salts has been developed to synthesize benzyl sulfones using Cs2CO3 as base under mild conditions. The protocol employs stable and easy to handle coupling partners, and is endowed with good substrate compatibility, leading to functional benzyl sulfones in good yields.
- Zhu, Haibo,Zhang, Yingying,Liu, Yishuai,Yang, Liu,Xie, Zongbo,Jiang, Guofang,Le, Zhang-Gao
-
supporting information
(2020/05/06)
-
- CuCl2-promoted decomposition of sulfonyl hydrazides for the synthesis of thiosulfonates
-
Sulfonyl hydrazides recently received much attention as reagents for the introduction of sulfur-containing functional groups into organic compounds, because both sulfonyl and sulfenyl sources could be generated by the oxidation and decomposition of the sulfonyl hydrazides, respectively. However, the transformations of sulfonyl hydrazides into thiosulfonates, which could be produced by the reaction between sulfonyl and sulfenyl sources, have been less investigated. In this manuscript, we describe CuCl2-promoted selective synthesis of thiosulfonates from sulfonyl hydrazides. A variety of thiosulfonates were produced in moderate to good yields. The mechanism involving radical intermediates such as sulfonyl radical and thiyl radical was proposed on the basis of the previously reported references and mechanistic investigations. In addition, quantum chemical simulations revealed that Cu-promoted decomposition of sulfonyl hydrazides is thermodynamically viable in the developed conditions.
- Kim, Junsu,Park, Sanggil,Kim, Hyungjun,Kim, Jinho
-
supporting information
(2020/07/02)
-
- An Alternative Metal-Free Aerobic Oxidative Cross-Dehydrogenative Coupling of Sulfonyl Hydrazides with Secondary Phosphine Oxides
-
An alternative metal-free, efficient and practical approach for the preparation of phosphinothioates is established via the aerobic oxidative cross-dehydrogenative coupling (CDC) of sulfonyl hydrazides with secondary phosphine oxides catalyzed by tetrabutylammonium iodide (TBAI) in the presence of atmospheric oxygen. The strategy provides an array of diverse phosphinothioates in good to excellent yields. Furthermore, two representative bioactive molecules are synthesized on up to gram scale by utilizing this method.
- Cheng, Feixiang,Liu, Jianjun,Liu, Teng,Yu, Rong,Zhang, Yanqiong
-
p. 253 - 262
(2019/12/28)
-
- Metal-Free Electrochemical Coupling of Vinyl Azides: Synthesis of Phenanthridines and β-Ketosulfones
-
We reported an efficient and environmentally benign electrochemical synthesis of phenanthridines by oxidative coupling of vinyl azides with sodium azide or benzenesulfonyl hydrazides, for the first time. The reaction conditions are mild, and no additional metal-catalyst or exogenous oxidants are needed. The protocol has broad substrate scope and high functional group tolerance. Furthermore, this green electrochemical procedure can be readily extended to the synthesis of β-ketosulfones. Gram scale reactions further demonstrate the practicability.
- Chen, Qianjin,Kong, Xianqiang,Li, Guodong,Liang, Qi,Lin, Long,Xu, Bo,Yu, Ke
-
supporting information
p. 6135 - 6145
(2020/10/06)
-
- One-pot synthesis of β-ketosulfones from sulfonyl chloride, hydrazine hydrate and vinyl azide in water
-
A novel, facile and efficient strategy for the one-pot synthesis of β-ketosulfones from readily available sulfonyl chloride, hydrazine hydrate and vinyl azides is described. The reaction proceeded very smoothly affording diverse β-ketosulfones in moderate to good yields. This new procedure has the advantages of environmental benign, easy and simple operation, low cost and wide tolerance of functional groups, which provides a highly fascinating protocol to access β-ketosulfones.
- Zhang, Yaohong,Luo, Mengqiang,Li, Yan,Shen, Runfu,Qi, Chenze,Wang, Hai,Cheng, Kai
-
supporting information
(2020/10/26)
-
- Synthesis of 3,4-Dihydrobenzo[f]phthalazines via Iodine/tert-Butyl Hydroperoxide-Mediated Annulation Cascade of Yne-Allenones
-
An iodine (I2)/tert-butyl hydroperoxide (TBHP)-mediated annulation cascade between yne-allenones and sulfonyl hydrazides has been established, in which a wide set of dihydrobenzo[f]phthalazines were synthesized through one-pot, two-step strategy under metal-free conditions. The synthetic utility of these transformations leads to subsequent C?C and C?N bond-forming reactions to effectively build up functional aza-heterocycle with potential significance. (Figure presented.).
- Fu, Rong,Li, Meng-Fan,Zhou, Peng,Hao, Wen-Juan,Tu, Shu-Jiang,Jiang, Bo
-
supporting information
p. 2280 - 2285
(2019/04/13)
-
- Wittig Ylide Mediated Decomposition of N -Sulfonylhydrazones to Sulfinates
-
N-Sulfonylhydrazones generate sulfinates selectively when treated with a stabilized Wittig ylide in a polar aprotic solvent at elevated temperature. The transition metal and base free decomposition method is applicable to N-sulfonylhydrazones generated from a number of aromatic and heteroaromatic aldehydes and ketones. In the case of N-tosylhydrazones derived from O-allyl and O-propargyl salicylaldehydes, selective formation of sulfinate occurs over intramolecular [3 + 2]-cycloaddition reaction.
- Choudhary, Deepika,Khatri, Vineeta,Basak, Ashok K.
-
supporting information
p. 1703 - 1706
(2018/04/14)
-
- Gold-Catalyzed Dehydrazinative C(sp)–S Coupling Reactions of Arylsulfonyl Hydrazides with Ethynylbenziodoxolones for Accessing Alkynyl Sulfones
-
A gold(III)-catalyzed dehydrazinative coupling reaction between arylsulfonyl hydrazides and ethynylbenziodoxolone reagents was realized for the synthesis of alkynyl sulfones. The scope and versatility of the reaction were demonstrated by the efficient synthesis of 23 derivatives with diverse structural features.
- Shinde, Popat S.,Patil, Nitin T.
-
p. 3512 - 3515
(2017/07/04)
-
- Synthesis, biological activities and molecular docking simulation of hydrazone scaffolds of carvacrol, thymol and eugenol
-
In present work, we report the synthesis of 12 new hydrazones and sulfonyl hydrazones linkage containing carvacrol, thymol and eugenol derivatives by simple condensation reactions. Synthesized derivatives have been characterized by 1H NMR, 13C NMR, LC–MS, and X-ray single crystallography techniques, and these derivatives were screened for anticancer testing by using sulforhodamine B assay and anti-oxidant testing by using DPPH assay. Docking studies of all the derivatives against the active site of human heme oxygenase-1 indicated that interaction with the maximum site of the amino acid residue of human heme oxygenase-1 was crucial for anti-oxidant activity. The results show that all derivatives possess interesting biological activities.
- Rajput, Jamatsing D.,Bagul, Suresh D.,Bendre, Ratnamala S.
-
p. 6601 - 6616
(2017/10/05)
-
- Copper-Catalyzed Aerobic Oxidative Reaction of Sulfonyl Hydrazides with Alcohols: An Easy Access to Sulfinates
-
A Cu-catalyzed aerobic oxidative reaction between sulfonyl hydrazides and alcohols has been developed. In this reaction, sulfonyl hydrazides act as the sulfinic acid precursors to react with alcohols, resulting in sulfinic esters with up to 72 % yield. This catalytic system tolerates a wide range of sulfonyl hydrazide substrates, and represents a new strategy for the transformation of readily available sulfonyl hydrazides.
- Du, Bingnan,Li, Zan,Qian, Ping,Han, Jianlin,Pan, Yi
-
supporting information
p. 478 - 481
(2016/03/08)
-
- Synthesis and potential anticonvulsant activity of new aryl sulfonyl semicarbazide derivatives
-
In the present study on the development of new anticonvulsants, twelve new aryl sulfonyl semicarbazide derivatives were synthesized and tested for anticonvulsant activity using maximal electroshock (MES), subcutaneous pentylenetetrazole screens. Their neurotoxicity was determined by the rotorod test. The most active compound 5i showed the MES-induced seizures with ED50 value of 7.3?mg/kg and TD50 value of 402.3?mg/kg after intraperitoneally injection to mice, which provided compound 5i with a protective index (TD50/ED50) of 55.1 in the MES test.
- Nie, Yousong,Zhong, Min,Jiang, Zhiyuan,Sun, Jian,Gao, Yangguang,Ding, Fei,Li, Hang,Zhang, Yongmin,He, Xianran
-
p. 1425 - 1432
(2016/07/06)
-
- Iodine-catalyzed expeditious synthesis of sulfonamides from sulfonyl hydrazides and amines
-
A new synthesis of sulfonamides has been developed via an iodine-catalyzed sulfonylation of amines with arylsulfonyl hydrazides. This metal-free strategy employs readily accessible and easy to handle starting materials, catalysts and oxidants, and can be easily conducted under mild conditions, providing a convenient access to a wide range of sulfonamides in moderate to excellent yields within a short reaction time.
- Yotphan, Sirilata,Sumunnee, Ladawan,Beukeaw, Danupat,Buathongjan, Chonchanok,Reutrakul, Vichai
-
supporting information
p. 590 - 597
(2016/01/12)
-
- SAMDI Mass Spectrometry-Enabled High-Throughput Optimization of a Traceless Petasis Reaction
-
Development of the self-assembled monolayer/MALDI mass spectrometry (SAMDI) platform to enable a high-throughput optimization of a traceless Petasis reaction is described. More than 1800 unique reactions were conducted simultaneously on an array of self-assembled monolayers of alkanethiolates on gold to arrive at optimized conditions, which were then successfully transferred to the solution phase. The utility of this reaction was validated by the efficient synthesis of a variety of di- and trisubstituted allenes.
- Diagne, Abdallah B.,Li, Shuheng,Perkowski, Gregory A.,Mrksich, Milan,Thomson, Regan J.
-
supporting information
p. 658 - 662
(2015/11/17)
-
- Oxidative Mizoroki-Heck-type reaction of arylsulfonyl hydrazides for a highly regio- and stereoselective synthesis of polysubstituted alkenes
-
A useful source: Arylsulfonyl hydrazides have been identified as synthetically useful aryl sources for the Pd(OAc)2 catalyzed oxidative Mizoroki-Heck-type reaction under molecular oxygen to provide a convenient access to polysubstituted alkenes in a highly regio- and stereoselective manner (see scheme). The reaction well tolerates various functional groups such as alkoxy, halo, alcohol, carboxylic acid, ester, amide, sulfonamide, and sulfone. Copyright
- Yang, Fu-Lai,Ma, Xian-Tao,Tian, Shi-Kai
-
supporting information; experimental part
p. 1582 - 1585
(2012/03/11)
-
- N-aryl-2-oxazolidinone-5-carboxamides and their derivatives
-
The present invention provides antibacterial agents having the formulae I, II, and III described herein.
- -
-
-
- N-ARYL-2-OXAZOLIDINONE-5-CARBOXAMIDES AND THEIR DERIVATIVES AND THEIR USE AS ANTIBACTERIALS
-
Compounds of formula B-C-A-CO-NH-R1, wherein A is structure i, ii or iii: formulae (I), (II), (III). C is optionally substituted aryl or heteroaryl, and B is a specified cyclic moiety, or C and B together are a heterobicyclic moiety, are useful as antibacterial agents.
- -
-
Page/Page column 135
(2010/02/07)
-
- N-arylsulfonyl hydrazones as inhibitors of IMP-1 metallo-β-lactamase
-
Members of a family of N-arylsulfonyl hydrazones have been identified as novel inhibitors of IMP-1, a metallo-β-lactamase of increasing prevalence. Structure-activity relationship studies have indicated a requirement for bulky aromatic substituents on each side of the sulfonyl hydrazone backbone for these compounds to serve as efficient inhibitors of IMP-1. Molecular modeling has provided insight into the structural basis for the anti-metallo-β-lactamase activity exhibited by this class of compounds.
- Siemann, Stefan,Evanoff, Darryl P.,Marrone, Laura,Clarke, Anthony J.,Viswanatha, Thammaiah,Dmitrienko, Gary I.
-
p. 2450 - 2457
(2007/10/03)
-