156787-63-2

Upstream product

• 591-50-4 iodobenzene 
• 119072-55-8 tert-butylisonitrile 
• 4274-38-8 2-amino-4-(trifluoromethyl)benzenethiol hydrochloride 
• 103-82-2 phenylacetic acid 
• 121-17-5 2-chloro-3-nitro-5-trifluoromethylbenzene 
• 860-39-9 bis(2-nitro-4-trifluoromethylphenyl) disulfide 
• 100-46-9 benzylamine 
• 603-33-8 triphenylbismuthane 
• 23420-87-3 5-(trifluoromethyl)benzo[d]thiazole-2(3H)-thione 
• 100-52-7 benzaldehyde 
• 19406-49-6 2-amino-4-trifluoromethylthiophenol 
• 100-51-6 benzyl alcohol 
• 618-31-5 benzylidene dibromide 
• 108-86-1 bromobenzene 

Downstream Products

• 1097023-62-5 2-(5-(trifluoromethyl)benzo[d]thiazol-2-yl)phenol 

Relevant academic research and scientific papers

Benzothiazole Synthesis: Mechanistic Investigation of an in Situ-Generated Photosensitizing Disulfide

The use of a visible light absorbing intermediate as a photosensitizer makes a chemical process simple and sustainable, obviating the need for the use of chemical additives. Herein, the formation of a photosensitizing disulfide in benzothiazole synthesis from 2-Aminothiophenol and aldehydes was proposed and confirmed through in-depth mechanistic studies. A series of photophysical and electrochemical investigations revealed that an in situ-generated disulfide photosensitizes molecular oxygen to generate the key oxidants, singlet oxygen and superoxide anion, for the dehydrogenation step.

Visible-light-induced tandem reaction of o-aminothiophenols and alcohols to benzothiazoles over Fe-based MOFs: Influence of the structure elucidated by transient absorption spectroscopy

MIL-100(Fe) and MIL-68(Fe), two Fe-based MOFs, were found to be active for oxidative condensation between alcohols and o-aminothiophenols to form 2-substituted benzothiazoles under visible light irradiation using oxygen (O2) as oxidant. This reaction can be applied to a wide range of substrates with medium to high yield. Controlled experiments and ESR results revealed a superoxide radical (O2-)-mediated pathway, which is derived from the reduction of O2 by photogenerated Fe2+ on Fe–O clusters. The whole multistep reaction is limited by the step of the photo-oxidation of alcohols to aldehydes. MIL-100(Fe) showed catalytic performance superior to that of MIL-68(Fe) because its higher concentration of long-lived (μs time scale) positive holes can be photogenerated over MIL-100(Fe), in contrast to MIL-68(Fe). This study not only provides an economical, sustainable, and thus green process for the production of 2-substituted benzothiazoles, but also illustrates the potential of using transient absorption spectroscopy as an important tool for understanding the photophysics of MOFs, which are believed to show great potential as multifunctional catalysts for light-induced organic transformations.

Sulfur-Promoted Redox Cyclization of 2,2′-Dinitrodiphenyl Disulfides and Benzylamines

This study aims to develop green and sustainable advanced synthetic methods based on redox cyclization. Elemental sulfur is shown to promote the efficient synthesis of 2-substituted benzothiazoles from 2,2′-dinitrodiphenyl disulfides and benzylamines via redox cyclization in the absence of transition-metal catalysts and solvents. The 2-substituted benzothiazoles are obtained in good to excellent yields. This synthetic methodology is highly atom-economical and does not require any external oxidizing and/or reducing agents.

A fluorinated phenylbenzothiazole arrests the trypanosoma cruzi cell cycle and diminishes the infection of mammalian host cells

Chagas disease (CD) is a human infection caused by Trypanosoma cruzi. CD was traditionally endemic to the Americas; however, due to migration it has spread to countries where it is not endemic. The current chemotherapy to treat CD induces several side eff

Liebeskind-Srogl-type cross-coupling reaction of azole-2-thiones with triarylbismuthines: Synthesis of 2-arylazoles

Liebeskind-Srogl-type C(HetAr)–C(Ar) bond formation using trivalent organobismuth compounds as a new class of arylating reagents is described. The reaction of benzazole-2-thiones with triarylbismuthines in the presence of 10 mol% Pd(dba)2 and 2.0 equiv. Cu(OAc)2 at 80 °C affords 2-arylbenzothiazoles, benzoxazoles, and N-methyl benzimidazole in moderate-to-high yield. The reaction is sensitive to the electronic nature of triarylbismuthines: compounds bearing an electron-withdrawing group on the phenyl ring showed higher reactivity than those having an electron-donating group.

Elemental sulfur as a polyvalent reagent in redox condensation with: O -chloronitrobenzenes and benzaldehydes: Three-component access to 2-arylbenzothiazoles

Sulfur was found to be a polyvalent reagent in the multicomponent redox condensation with o-chloronitrobenzenes and benzaldehydes. 2-Arylbenzothiazoles was obtained in moderate to good yields in a highly atom-economical pathway.

Palladium catalyzed Csp2-H activation for direct aryl hydroxylation: The unprecedented role of 1,4-dioxane as a source of hydroxyl radicals

A novel strategy for direct aryl hydroxylation via Pd-catalysed Csp2-H activation through an unprecedented hydroxyl radical transfer from 1,4-dioxane, used as a solvent, is reported with bio relevant and sterically hindered heterocycles and various acyclic functionalities as versatile directing groups.

Elemental sulfur mediated decarboxylative redox cyclization reaction of o -chloronitroarenes and arylacetic acids

A decarboxylative redox cyclization strategy has been developed for the synthesis of 2-substituted benzothiazoles by the reaction of o-chloronitroarenes and arylacetic acids in the presence of elemental sulfur/N-methylmorpholine under metal- and solvent-free conditions.

METHOD FOR PREPARING BENZOTHIAZOLE AND DERIVATIVES

The present invention relates to a method for preparing benzothiazole and derivatives of the same and, more specifically, to a method for preparing benzothiazole derivatives using aminothiophenol derivatives, aldehyde, oxygen, and photocatalyst under the condition in which visible rays are radiated to react in a simple condition while synthesizing benzothiazole derivatives having various forms in high yield.COPYRIGHT KIPO 2015

Elemental sulfur disproportionation in the redox condensation reaction between o-halonitrobenzenes and benzylamines

The disproportionation of elemental sulfur at moderate temperatures is investigated in the redox condensation involving o-halonitrobenzenes 1 and benzylamines 2. As a redox moderator, elemental sulfur plays the dual role of both electron donor and acceptor, generating its lowest and highest oxidation states: S-2 (sulfide equivalent) in benzothiazole 3 and S+6 (sulfate equivalent) in sulfamate 4, and filling the electron gap of the global redox condensation process. Along with this process, a cascade of reactions of reduction of the nitro group of 1, oxidation of the aminomethyl group of 2, metal-free aromatic halogen substitution, and condensation finally led to 2-arylbenzothiazoles 3.