67219-33-4

Upstream product

• 19654-17-2 2-benzylthiobenzothiazole 
• 149-30-4 2-Mercaptobenzothiazole 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 100-51-6 benzyl alcohol 
• 7778-70-3 potassium 2-mercaptobenzothiazolate 
• 2492-26-4 sodium 2-mercaptobenzothiazole 

Downstream Products

• 1202-49-9 (E)-2-styrylfuran 
• 1271301-08-6 tert-butyl 2-(benzo[d]thiazol-2-ylsulfonyl)-2-phenylacetate 
• 1271301-06-4 methyl 2-(benzo[d]thiazol-2-ylsulfonyl)-2-phenylacetate 
• 51793-64-7 sodium α-toluenesulfinate 
• 101-41-7 benzeneacetic acid methyl ester 
• 16537-11-4 tert-butyl 4-phenylbutanoate 
• 101306-31-4 benzyl cinnamyl ether 
• 101306-31-4 (Z)-(3-(benzyloxy)prop-1-en-1-yl)benzene 
• 27066-35-9 (E)-1,4-diphenylbut-1-ene 
• 70388-65-7 (Z)-1,4-diphenyl-1-butene 
• 696-31-1 α-fluorostyrene 
• 886206-84-4 1,3-benzothiazol-2-yl (phenyl)fluoromethyl sulfone 
• 1332866-18-8 C₁₈H₁₇ClO₂ 
• 1332866-17-7 C₂₅H₂₀ClNO₄S₂ 

Relevant academic research and scientific papers

Redox-active alkylsulfones as precursors for alkyl radicals under photoredox catalysis

A method for generating alkyl radicals using visible-light photoredox catalysis is described. This procedure was found to present an efficient means to access a diverse collection of 1°, 2°, and 3° alkyl radicals through the single-electron transfer of sulfones under mild reaction conditions. These alkyl radicals generated via the reductive desulfonylation of readily synthesized and stable alkylsulfones were engaged to forge C-C bonds. A detailed study was also carried out to shed light on the mechanism.

Conformational Analysis of Acyclic α-Fluoro Sulfur Motifs

Bioactive small molecules containing α-fluoro sulfur motifs [RS(O)nCH2F] are appearing with increasing frequency in the pharmaceutical and agrochemical sectors. Prominent examples include the anti-asthma drug Flovent and t

One-pot sequential synthesis and antifungal activity of 2-(benzylsulfonyl)benzothiazole derivatives

New antifungal agrochemicals, derived from 2-(benzylsulfonyl)benzothiazole were synthesized by an environmentally friendly method, using water as reaction medium. These compounds were prepared by a one-pot, two-step synthesis, starting from 2-mercaptobenzothiazole and benzyl halides. The potential fungicides were tested against a panel of phytopathogenic fungi, with many of them showing a significant improvement compared to the non-oxidized analogues and the commercial antifungal Captan. The new derivatives 2-((2-chlorobenzyl)sulfonyl)benzo[d]thiazole (4f) and 2-((4-methylbenzyl)sulfonyl)benzo[d]thiazole (4k) presented remarkable properties, being able to inhibit the growth of two resistant moulds (Aspergillus fumigatus and Aspergillus ustus). Both 4f and 4k could be classified as broad-spectrum fungicides, emerging as possible candidates for the control of these moulds, which have negative impact in food production.

One and Two-Carbon Homologation of Primary and Secondary Alcohols to Corresponding Carboxylic Esters Using β-Carbonyl BT Sulfones as a Common Intermediate

Herein we report the efficient one- and two-carbon homologation of 1° and 2° alcohols to their corresponding homologated esters via the Mitsunobu reaction using β-carbonyl benzothiazole (BT) sulfone intermediates. The one-carbon homologation approach uses standard Mitsunobu C-S bond formation, oxidation and subsequent alkylation, while the two-carbon homologation uses a less common C-C bond forming Mitsunobu reaction. In this latter case, the use of β-BT sulfone bearing esters lowers the pKa sufficiently enough for the substrate to be used as a carbon-based nucleophile and deliver the homologated β-BT sulfone ester, and this superfluous sulfone group can then be cleaved. In this paper we describe several methods for the effective desulfonylation of BT sulfones and have developed methodology for one-pot alkylation-desulfonylation sequences. As such, overall, a one-carbon homologation sequence can be achieved in a two-pot (four step) procedure and the two-carbon homologation in a two-pot (three step) procedure (three-pot; four step when C-acid synthesis is included). This methodology has been applied to a wide variety of functionality (esters, silyl ethers, benzyls, heteroaryls, ketones, olefins and alkynes) and are all tolerated well providing good to very good overall yields. The power of our method was demonstrated in site-selective ingenol C20 allylic alcohol two-carbon homologation.

Benzothiazole Sulfinate: A Sulfinic Acid Transfer Reagent under Oxidation-Free Conditions

Sulfinic acids are commonly encountered intermediates found in natural product synthesis and medicinal chemistry. However, because of high reactivity, instability, and harsh reaction conditions, they are difficult to synthesize. Herein we have developed an oxidation-free method to produce sulfinic acids and sulfinate salts using 2-sulfinyl benzothiazole (BTS). We have also demonstrated the synthetic usefulness by developing one-pot syntheses of sulfones and sulfonamides.

Practical synthesis of β-oxo benzo[d]thiazolyl sulfones: Scope and limitations

In this paper, we discuss our new synthetic approach towards functionalized benzo[d]thiazolyl (BT) sulfones, based on the reunion of alkyl BT sulfones and various electrophiles (e.g. R-CO-X, RO-CO-X, RS-CO-X, Ts-X...). All important aspects of this coupling reaction, including relevant and undesirable side reactions, are evaluated by means of calculations and competitive experiments. The scope and limitations of this method are established. The Royal Society of Chemistry 2012.

Practical synthesis of β-acyl and β-alkoxycarbonyl heterocyclic sulfones

A short and efficient synthesis for β-acyl and β-alkoxycarbonyl heterocyclic sulfones containing benzothiazol (BT) and phenyltetrazol (PT) heterocyclic core is presented here. The method seems to be general and provides the desired C-nucleophiles in very good to excellent yields from readily available starting materials.

Chemoselective sulfoxidation by H2O2 or HNO3 using a phosphate impregnated titania catalyst

A variety of organosulfur compounds have been selectively oxidized to the corresponding sulfoxides by either H2O2 or HNO3 using a newly developed solid acid catalyst composed of 84.5% of TiO2 and 15.5% of [Ti4H11(PO4)9]·nH2O (n = 1-4). The chemoselective oxidation of sulfides in the presence of vulnerable groups such as -CN, -C{double bond, long}C-, -CHO, or -OH, as well as sulfoxidation of substrates like benzothiazole, glycosyl sulfide, and dibenzothiophenes is some of the important attribute of the protocol. Nitric acid, under the present experimental conditions, brings about relatively better selectivity than hydrogen peroxide.

Fast and efficient oxidation of sulfides to sulfones with N,N′-dibenzyl-N,N,N′,N′-tetramethyl diammonium permanganate

Selective oxidation of sulfides to sulfones was developed using N,N′-dibenzyl-N,N,N′,N′-tetramethylethylene diammonium permanganate. A variety of aromatic and aliphatic sulfides were oxidized to the corresponding sulfones immediately in excellent yields at r.t. Copyright Taylor & Francis Group, LLC.

THIOREDOXIN AND THIOREDOXIN REDUCTASE INHIBITORS

The present invention relates to sulfone derivatives and to their use as modulators of the thioredoxin/thioredoxin reductase redox system, including for the treatment and/or prevention of pathophysiological conditions mediated by thioredoxin/thioredoxin reductase, such as cancer, HIV/ AIDS, Alzheimer's disease, rheumatoid arthritis, and skin disorders. Also provided are pharmaceutical compositions comprising the inventive sulfones.