5707-04-0Relevant articles and documents
Interaction of difluoromethylene phosphobetaine with heteroatom-centered electrophiles
Trifonov, Alexey L.,Panferova, Liubov I.,Levin, Vitalij V.,Volodin, Alexander D.,Korlyukov, Alexander A.,Dilman, Alexander D.
, p. 78 - 82 (2019)
A series of difluorinated phosphonium salts were obtained by reaction of difluoromethylene phosphobetaine with halogenating reagents, as well as arylsulfenyl and arylselenyl chlorides. The reaction proceeds via decarboxylation of the phosphobetaine followed by trapping of the difluorinated phosphorus ylide by heteroatom-centered electrophiles. The crystal structures of the phosphonium salts were studied by X-ray diffraction analysis. For the salt containing the CF2I group and iodide counterion, the I?I interaction was identified in the solid state. The nature of this halogen bond was evaluated by quantum chemical calculations.
Intramolecular Chalcogenylation of Isooxazolines Mediated by PhICl 2and Diorganyl Disulfides or Diselenides
Zhang, Dongke,Zhang, Jingran,Li, Xiaoxian,Yu, Zhenyang,Li, Yadong,Sun, Fengxia,Du, Yunfei
, p. 411 - 420 (2021/10/05)
Reactive organosulfenyl chlorides (ArSCl) or selenenyl chlorides (ArSeCl), generated in situ from the reaction of PhICl 2with diorganyl disulfides or diselenides, enable the intramolecular oxidative cyclization/chalcogenylation of β,γ-unsaturated oximes, leading to the formation of a series of chalcogenylated isooxazolines in good to excellent yield.
Preparation of selenyl 1,3-oxazines: Via PhICl2/Cu2O-promoted aminoselenation of O -homoallyl benzimidates with diselenides
Zhang, Linlin,Qi, Lin,Chen, Jia-Min,Dong, Wei,Fang, Zhuo-Yue,Cao, Tong-Yang,Li, Wei,Wang, Li-Jing
supporting information, p. 12655 - 12658 (2021/12/07)
A practical electrophilic aminoselenation of O-homoallyl benzimidate with diselenides promoted by PhICl2/Cu2O has been developed. The easily available and stable diselenides were used as selenium sources. Various selenyl 1,3-oxazines, which are important frameworks in medicinal and biological chemistry, were easily obtained in moderate to good yields for the first time. Easy scaleup and scalability make this method attractive for the preparation of other valuable organoselenides.
Synthesis of 4-chalcogenyl pyrazoles via electrophilic chalcogenation/cyclization of α,β-alkynic hydrazones
Cheng, Yu-Fei,Gao, Wen-Chao,Niu, Yulan,Shang, Yu-Zhu,Tian, Jun,Yu, Xinzhang
, p. 1806 - 1811 (2020/03/17)
A facile method for the synthesis of 4-chalcogenylated pyrazoles has been developed via electrophilic chalcogenation/cyclization of α,β-alkynic hydrazones. The cyclization of α,β-alkynic aldehyde hydrazones could be induced by using either sulfenyl chloride or the S-electrophiles generated in situ from the reaction of NCS and arythiol. The developed method was successfully applied to the synthesis of the sulfenyl analogue of celecoxib.
In Situ Formation of RSCl/ArSeCl and Their Application to the Synthesis of 4-Chalcogenylisocumarins/Pyrones from o-(1-Alkynyl)benzoates and (Z)-2-Alken-4-ynoates
Xing, Linlin,Zhang, Yong,Li, Bing,Du, Yunfei
supporting information, p. 3620 - 3624 (2019/05/24)
The reaction of diorganyl disulfides or diselenides with PhICl2 in acetonitrile was found for the first time to lead to the in situ formation of organosulfenyl chloride or selenenyl chloride, which enables the regioselective intramolecular chalcogenylacyloxylation of alkynes resulting in the formation of 4-chalcogenylisocumarins/pyrones in good to excellent yields under metal-free conditions.
Synthetic method of aryl sulfur chlorine or aryl selenium chlorine
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Paragraph 0034-0037, (2019/06/27)
The invention discloses a synthetic method of aryl sulfur chlorine or aryl selenium chlorine. The synthetic method comprises the following steps that diaryl disulfide or diaryl diselenide II is dissolved in a solvent and reacts under the action of dichloro-iodobenzene III to obtain aryl sulfur chlorine or aryl selenium chlorine I. In the formula shown in the description, R refers to hydrogen, methyl or halogen, and Y refers to sulfur or selenium. The method has the advantages that the operation is simple, the raw materials are cheap and easy to obtain, the yield is relatively ideal and the cost is low.
in situ Formation of RSCl/ArSeCl and Their Oxidative Coupling with Enaminone Derivatives Under Transition-metal Free Conditions
Shang, Zhenhua,Chen, Qingyu,Xing, Linlin,Zhang, Yilin,Wait, Laura,Du, Yunfei
supporting information, p. 4926 - 4932 (2019/11/03)
The reaction of diorganyl disulfides or diselenides with PhICl2 in DMF at room temperature led to the in situ formation of the reactive organosulfenyl chloride (RSCl) or selenenyl chloride (ArSeCl), which reacted with enaminone compounds to afford a series of α-thioenaminones or α-selenylenaminones, respectively, including the bioactive inhibitor for Cdc25B and its analogue, via the intermolecular oxidative C(sp2)-S/Se cross coupling reactions under metal-free conditions. (Figure presented.).
Copper complexes and carbon nanotube-copper ferrite-catalyzed benzenoid A-ring selenation of quinones: An efficient method for the synthesis of trypanocidal agents
Jardim, Guilherme A.M.,Bozzi, ícaro A.O.,Oliveira, Willian X.C.,Mesquita-Rodrigues, Camila,Menna-Barreto, Rubem F.S.,Kumar, Ramar A.,Gravel, Edmond,Doris, Eric,Braga, Antonio L.,Da Silva Júnior, Eufranio N.
, p. 13751 - 13763 (2019/09/16)
We report a new method for A-ring selenation of naphthoquinones and anthraquinones and discuss the relevant trypanocidal activity of the synthesized compounds. We have demonstrated three efficient strategies for the preparation of the target selenium derivatives, i.e. (a) copper(i) thiophene-2-carboxylate and in situ generated Santi's reagent were used to prepare selenium-substituted benzenoid quinones, (b) copper complexes and (c) carbon nanotube-supported copper ferrite as catalysts in the presence of AgSeR-salts were also used for the synthesis of selenium-containing quinoidal derivatives. These new methods provide efficient and practical strategies for the preparation of selenium-based quinones. In addition, we have discovered nine compounds with potent trypanocidal activity. The derivatives 2a-2e showed potent trypanocidal activity with IC50 values in the range of 13.3 to 37.0 μM.
Acyl Selenyl Sulfides as the Precursors for Reactive Sulfur Species (Hydrogen Sulfide, Polysulfide, and Selenyl Sulfide)
Hamsath, Akil,Wang, Yingying,Yang, Chun-Tao,Xu, Shi,Ca?edo, Danica,Chen, Wei,Xian, Ming
supporting information, p. 5685 - 5688 (2019/08/01)
Persulfides are receiving increased attention due to their links to hydrogen sulfide (H2S) and hydrogen polysulfide (H2Sn). Their close analogues selenyl sulfides (RSeSHs), however, have limited literature precedent, and their reactivity and possible role in biology are largely unknown. Here, we devised an acyl selenyl sulfide template to study RSeSH chemistry. Their stability and reactivity toward amines/thiols were studied. These compounds can produce H2S or H2S2 under different conditions, suggesting that RSeSHs are possible intermediates.
Reactivity of extended chalcogen-nitrogen π-systems: Compounds Ar-Se-N=S=N-Se-Ar
Makarov, Arkady G.,Grayfer, Tatiana D.,Makarov, Alexander Yu.,Bagryanskaya, Irina Yu.,Vasiliev, Vladimir G.,Zibarev, Andrey V.
scheme or table, p. 320 - 322 (2012/02/06)
The reactions of Ar-Se-N=S=N-Se-Ar with SO2Cl2 (as well as with ArSeCl and p-TolICl2) and H2O gave Ar-SeCl2-N=S=N-Se-Ar and [NH4]+[ArSeSO 3]- (Se-Bunte salts), respectively, whose structures were confirmed by X-ray diffraction.
