758716-82-4

Upstream product

• 349-95-1 4-(trifluoromethyl)benzylic alcohol 
• 149-30-4 2-Mercaptobenzothiazole 
• 939-99-1 4-trifluoromethylbenzyl chloride 

Downstream Products

• 1259948-51-0 2-((4-(trifluoromethyl)benzyl)sulfonyl)benzo[d]thiazole 

Relevant academic research and scientific papers

Green Synthesis of Potential Antifungal Agents: 2-Benzyl Substituted Thiobenzoazoles

A series of benzyl-substituted thiobenzoazoles were synthesized by an environmentally friendly approach, to search for new antifungal agrochemicals. Compounds were prepared starting from 2-mercaptobenzoazoles, using KOH, benzyl halides, and water, resulting in a simple and ecological method. New antifungals were tested against a group of phytopathogenic fungi. Two compounds showed an interesting activity against Botrytis cinerea, Fusarium oxysporum, and Aspergillus spp.: 2-((4-(trifluoromethyl)benzyl)thio)benzo[d]thiazole, 3ac, and 2-((4-methylbenzyl)thio)benzo[d]thiazole, 3al. Thus, 3ac and 3al can be considered as broad spectrum antifungal agents. Furthermore, two new compounds, 2-((4-iodobenzyl)thio)benzo[d]thiazole, 3aj, and 2-(benzylthio)benzo[d]oxazole, 3ba, showed better inhibitory effect against Botrytis cinerea and Fusarium oxysporum when compared to the commercial fungicide Captan. Thus, 3aj and 3ba can be considered reduced-spectrum antifungals.

One-Pot Substitution of Aliphatic Alcohols Mediated by Sulfuryl Fluoride

The Mitsunobu reaction is a powerful transformation for the one-pot activation and substitution of aliphatic alcohols. Significant efforts have focused on modifying the classic conditions to overcome problems associated with purification from phosphine-based byproducts. Herein, we report a phosphine free method for alcohol activation and substitution that is mediated by sulfuryl fluoride. This new method is effective for a wide range of primary alcohols using phthalimide, di-tert-butyl-iminodicarboxylate, and aromatic thiol nucleophiles in 74 % average yield. Activated carbon nucleophiles and a deactivated phenol were also effective for this reaction in good yields. Secondary alcohols were also successful substrates using aryl thiols, affording the corresponding sulfides in 56 % average yield with enantiomeric ratios up to 99:1. This new protocol has a distinct synthetic advantage over many existing phosphine-based methods as the byproducts are readily separable. This feature was exploited in several examples that did not require chromatography for purification. Furthermore, the mild reaction conditions enabled further in situ derivatization for the one-pot conversion of alcohols to amines or sulfones. This method also provides a boarder nucleophile scope compared to existing phosphine-free methods.

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.

A Convenient, Mild, and Green Synthesis of NH-Sulfoximines in Flow Reactors

NH-sulfoximines are emerging as useful and important targets in drug discovery and synthetic organic chemistry. We report herein the development of an efficient, convenient, and sustainable continuous-flow strategy, for the direct, straightforward preparation of NH-sulfoximines by using sulfides or sulfoxides as suitable starting material. The flow process uses PhI(OAc)2 as the oxidant and aqueous solutions of ammonia as the N source. The scope of the reaction has been demonstrated by using several substituted sulfides and sulfoxides including enantioenriched and biologically relevant starting materials. The flow strategy was found to be more convenient with respect to conventional batch processing.

Structure-activity relationships of 2-benzylsulfanylbenzothiazoles: Synthesis and selective antimycobacterial properties

A set of 2-benzylsulfanyl derivatives of benzothiazole was synthesized and evaluated for antimicrobial and cytotoxic activities. The biological screening on antimicrobial activity against a panel of Gram-positive and Gramnegative bacteria, yeasts and fung

Novel aromatic fluoroolefins via fluoro-Julia-Kocienski olefination

Fluoroolefins, which play an increasingly important role as peptide mimics in pharmaceuticals and as crop protection agents, are generated using a fluoro-Julia-Kocienski olefination. Their preparation can easily be accomplished using a Mitsunobu reaction and subsequent oxidation to generate the required benzothiazolyl sulfones. The key step of this process was the electrophilic -fluorination of the sulfone with N-fluorobenzenesulfonimide. The last stage of the successful synthesis of the fluoroolefins was the modified Julia-Kocienski olefination under basic conditions. Further functionalization was followed with the application of a Suzuki reaction. Georg Thieme Verlag Stuttgart.