5831-37-8Relevant academic research and scientific papers
Oxidative radical coupling of hydroquinones and thiols using chromic acid: One-pot synthesis of quinonyl alkyl/aryl thioethers
Adarsh Krishna, T. P.,Chinnasamy, Suresh,Ilangovan, Andivelu,Pandaram, Sakthivel
, p. 19454 - 19462 (2020/06/04)
An efficient, simple and practical protocol for one-pot sequential oxidative radical C-H/S-H cross-coupling of thiols with hydroquinones (HQs) and oxidation leading to the formation of quinonyl alkyl/aryl thioethers using H2CrO4was developed. This cross-coupling of thiyl and aryl radicals offers mono thioethers in good to moderate yield and works well with a wide variety of thiols. Similarly, this method works well for coupling of 2-amino thiophenol and HQs to form phenothiazine-3-ones5a-c. C-S bond formationviathioether synthesis was observed using a chromium reagent for the first time. Theoretical studies on the pharmacokinetic properties of compounds5a-crevealed that due to drug-like properties, compound5bstrongly binds with Alzheimer's disease (AD) associated AChE target sites.
The convenient synthesis and reaction of 2-(arylthio)phenols under ligand-free conditions: arylthioquinone preparation through cascade C–H functionalization and oxidation from arylthiols and aryl iodides
Wang, Dawei,Yu, Xiaoli,Wang, Likui,Yao, Wei,Xu, Zhaojun,Wan, Huida
supporting information, p. 5211 - 5214 (2016/11/13)
A convenient and simple method for copper-catalyzed synthesis of 2-(arylthio)phenols through C–H functionalization of arylthiols and aryl iodides was developed under ligand-free conditions without nitrogen protection. In addition, arylthioquinone derivatives were very easily prepared for one more step of oxidation with moderate to good yields. This provide an alternative and efficient way to 2-(arylthio)phenols and arylthioquinone derivatives smoothly without using ligands and nitrogen protection or expensive arylboronic acids.
Copper and triphenylphosphine-promoted sulfenylation of quinones with arylsulfonyl chlorides
Yu, Xiaoli,Wu, Qiujin,Wan, Huida,Xu, Zhaojun,Xu, Xingle,Wang, Dawei
, p. 62298 - 62301 (2016/07/16)
The efficient copper and triphenylphosphine-promoted sulfenylation of quinones with arylsulfonyl chlorides has been developed under mild conditions with moderate to good yields. Significantly, this provides an alternative method to synthesise arylthioquinone derivatives. This is the first time that arylthioquinones with arylsulfonyl chlorides as starting material have been prepared, which avoids the use of the awful smelling thioalcohols and thiophenols.
Copper-Catalyzed Reaction Cascade of Thiophenol Hydroxylation and S-Arylation through Disulfide-Directed C-H Activation
Wang, Dawei,Yu, Xin,Yao, Wei,Hu, Wenkang,Ge, Chenyang,Shi, Xiaodong
supporting information, p. 5543 - 5546 (2016/04/20)
Copper-catalyzed thiophenol C-H activation is described. Through an initial attempt to conduct C-arylation with arylboronic acid, a rather surprising sequential C-H activation and S-arylation was discovered. Mechanistic investigation revealed the disulfide intermediate as the key component in directing C-H oxidation. The overall reaction proceeded under mild conditions with molecular oxygen as the oxidant. Discovery of disulfide as the directing group provides a potential new direction for catalytic C-H functionalization under mild conditions.
A convenient new route to 4-substituted benzo[de][3,6]phenanthrolin- 6(6H)-ones: Important intermediates in the synthesis of ring-A analogues of the cytotoxic marine alkaloid ascididemin
Copp, Brent R.,Hansen, Richard P.,Appleton, David R.,Lindsay, Brent S.,Squire, Chris J.,Clark, George R.,Rickard, Cliff E. F.
, p. 2665 - 2676 (2007/10/03)
4-ethylthio- and (4-(4''-methylphenylthio)benzo[de][3,6]phenanthrolin- 6-(6H)-one have been synthesised in 4 steps from benzoquinone and then readily converted to the 4-amino (6d) and 4-methoxy (6c) analogues by nucleophilic substitution. Further elaborat
GENERAL SYNTHESIS OF CHIRAL 2-P-TOLYLSULFINYLQUINONES
Carreno, M. Carmen,Ruano, Jose L. Garcia,Mata, Jose M.,Urbano, Antonio
, p. 605 - 614 (2007/10/02)
Optically pure (S)-p-tolylsulfinyl substituted quinones were synthesized by deketalization of the corresponding quinone bisketals obtained by Andersen's type synthesis starting from 2-bromo-1,4-dimethoxy aromatic derivatives, followed by anodic oxidation
Polymer-supported Periodate and Iodate as Oxidizing Agents
Harrison, Charles R.,Hodge, Philip
, p. 509 - 511 (2007/10/02)
The periodate forms of some commercial macroporous anion-exchange resins can be used in either protic or aprotic solvents to oxidize various quinols, catechols, and glycols and also triphenylphosphine, hydrazobenzene, and benzohydroxamic acid.The reagents in methanol oxidize thioethers.Polymer-supported iodate also oxidizes quinols and catechols.
Oxidation Reactions using Sodium Metaperiodate Supported on Silica Gel
Gupta, Dharmendra N.,Hodge, Philip,Davies, J. Eric
, p. 2970 - 2973 (2007/10/02)
No reaction occurred when solutions of 2,5-di-t-butylhydroquinone, dibenzyl sulphide, trans-cyclohexane-1,2-diol or hydrazobenzene in methylene chloride were stirred with powdered sodium metaperiodate at 20 deg C for several hours.However, these and several closely related substrates were oxidized in good yield, generally within a few hours, when solutions in methylene chloride, and in some cases benzene or ether, were stirred with sodium metaperiodate supported on silica gel.The supported reagent was prepared by evaporating to dryness an aqueous solution of sodium metaperiodate in the presence of silica gel, followed by heating at 120 deg C in vacuo.The reagent appears to consist mainly of a monomolecular layer of sodium metaperiodate bound to the silica gel by the surface hydroxy-groups, together with a minor amount of crystalline anhydrous sodium metaperiodate.
