Synthesis Of Thiosulfonates Research Articles

Metal‐Free Synthesis of Thiosulfonates via Insertion of Sulfur Dioxide

AbstractA simple and catalyst‐free strategy was developed for the synthesis of unsymmetrical thiosulfonates using readily available DABCO⋅(SO2)2 as a solid and bench‐stable sulfur dioxide surrogate. The corresponding thiosulfonates were obtained through a radical pathway with good functional group tolerance. This strategy offers a promising synthesis method for the construction of diverse and useful thiosulfonates in the field of synthetic and pharmaceutical chemistry and extends the number of still limited sulfur dioxide fixation strategies.magnified image

ChemInform Abstract: Copper‐Catalyzed Synthesis of Thiosulfonates by Oxidative Coupling of Thiols with Sodium Sulfinates.

AbstractThe title reaction proceeds in the presence of a CuI/phenanthroline catalyst and oxygen as terminal oxidant.

Copper‐Catalyzed Synthesis of Thiosulfonates by Oxidative Coupling of Thiols with Sodium Sulfinates

AbstractThe copper‐catalyzed sulfonylation of thiols was performed by using sodium sulfinates under an oxygen atmosphere. The procedure afforded thiosulfonates in good yields by using a CuI–Phen·H2O (Phen = 1,10‐phenanthroline) catalyst and tolerated numerous combinations of arene‐ and alkanethiols with sodium sulfinates. Furthermore, it was found that the coupling of diaryl disulfides with sodium arylsulfinates proceeded in air and both sulfide groups on the disulfide were available.

Strategies for the synthesis and molecular modeling aiming to discover biorational agricultural insecticides

This work presents two proposals for the synthesis of halogenated aryl thiosulfonates which are of biologically interesting compounds. Inhibitors of proteases and juvenile hormone mimetizing are already successfully employed for managing pest-insects However, many of these products can be always improved in the aspects of specificity implying in low cost to the farmer. The major objective of this work is the synthesis of thiosulfonates analogues of commercial products which are inhibitors of serine-protease and juvenile hormone mimetizing compounds that can be applied as leads for production of insecticides that can contribute to the control of pest-insects in economically important plantation and stored grains. The scientific research group SINTMOLB (CNPq) is involved with studies related to the synthesis of phenolic compounds with insecticidal potential. Some important results have already been obtained and, in this new project, it is being explored the synthesis of new compounds, computational analysis, and biological tests to evaluate protease inhibitory effect.

ChemInform Abstract: Zinc Dichromate Trihydrate (ZrCr2O7·3H2O) as an Efficient Reagent for the One‐Pot Synthesis of Thiosulfonates from Thiols.

AbstractA simple procedure is developed for the chemoselective oxidation of aryl and alkyl thiols providing thiosulfonates in high yields.

ChemInform Abstract: Synthesis of Heterocyclic Thiosulfonates.

A simple synthesis of heterocyclic thiosulfonates containing indole, indoline, benzoimidazole, and quinoxaline rings is described. The synthesis of these thiosulfonates involves the preparation of the appropriately substituted thiols followed by sulfonylation to give thiosulfonates. The corresponding thiols were prepared in a simple and efficient manner by using a thiocyanation reaction either prior to heterocycle ring formation or after heterocycle ring formation. These thiosulfonates were coupled successfully to the 5,6-dihydropyran-2-one ring to give products that showed excellent HIV protease activity.

ChemInform Abstract: Synthesis of Thiosulfonates with Functional Groups in the Aliphatic Chain.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Synthesis of Thiosulfonates with Functional Groups in the Aliphatic Chain

Thiosulfonates of the general formula RSO2SR 1 having functional substituents in the S-alkyl chain exhibit high biological activity; the presence of a hydroxy group increases their solubility in water [1, 2]. Esters containing hydroxy groups are usually obtained in poor yields (15340%) by alkylation of metal thiosulfonates with ethylene halohydrins in aqueous acetone on heating [2]. With the goal of searching for new methods of synthesis of thiosulfonates we have performed for the first time reactions of alkali metal thiosulfonates with oxiranes. By reaction of 2-chloromethyloxirane with alkali metal thiosulfonates in aqueous alcohol in the presence of Lewis acid at 20oC we have synthesized S-(2-hydroxy-3-chloropropyl) thiosulfonates in 56384% yield. We have thus demonstrated the possibility for opening of the oxirane ring by the action of thiosulfonic acid salts. Thio esters were derived from alkali metal salts of 3-acetylamino-4methoxybenzenethiosulfonic acid (Ia), 1,1-dioxotetrahydrothiophene-3-thiosulfonic acid (Ib), 4-acetylaminobenzenethiosulfonic acid (Ic), 4-toluenethiosulfonic acid (Id), and benzenethiosulfonic acid (Ie).

S-tosylsulfenamides, new electrophilic sulfosulfenylating agents

A method has been developed for the synthesis of thiosulfonates by the electrophilic addition of S-tosylsulfenamides to olefins or their electrophilic substitution in aromatic systems. SO3, Py·SO3, and BF3·Et2O were used as activators. The addition of S-tosylsulfenamides to olefins proceeds through electrophilic trans addition.

ChemInform Abstract: Benzopentathiepin as Sulfurization Reagent. Novel Synthesis of Thiosulfonates (II) from Sulfinates (I).

ChemInform Abstract: Benzopentathiepin as Sulfurization Reagent. Novel Synthesis of Thiosulfonates (II) from Sulfinates (I).

Benzopentathiepin as Sulfurization Reagent. Novel Synthesis of Thiosulfonates from Sulfinates

Abstract Sodium alkane- and arenesulfinates were readily sulfurized with benzopentathiepin in usual organic solvents at room temperature to give corresponding thiosulfonates in good yields.