1629-23-8

Upstream product

• 38985-64-7 o-fluorophenyl isothiocyanate 
• 367-97-5 N-(2-fluorophenyl)benzenamine 
• 348-54-9 2-Fluoroaniline 
• 98-88-4 benzoyl chloride 
• 93-58-3 benzoic acid methyl ester 

Downstream Products

• 883-93-2 2-Phenylbenzothiazole 
• 367-97-5 N-(2-fluorophenyl)benzenamine 
• 1629-92-1 4-fluoro-2-phenylbenzo[d]thiazole 

Relevant academic research and scientific papers

Development of a 1,2,4-Triazole-Based Lead Tankyrase Inhibitor: Part II

Tankyrase 1 and 2 (TNKS1/2) catalyze post-translational modification by poly-ADP-ribosylation of a plethora of target proteins. In this function, TNKS1/2 also impact the WNT/β-catenin and Hippo signaling pathways that are involved in numerous human diseas

Exogenous Photosensitizer-, Metal-, and Base-Free Visible-Light-Promoted C-H Thiolation via Reverse Hydrogen Atom Transfer

Visible-light-driven, intramolecular C(sp2)-H thiolation has been achieved without addition of a photosensitizer, metal catalyst, or base. This reaction induces the cyclization of thiobenzanilides to benzothiazoles. The substrate absorbs visible light, and its excited state undergoes a reverse hydrogen-atom transfer (RHAT) with 2,2,6,6-tetramethylpiperidine N-oxyl to form a sulfur radical. The addition of the sulfur radical to the benzene ring gives an aryl radical, which then rearomatizes to benzothiazole via RHAT.

Palladium-catalyzed C-H cyclization in water: A milder route to 2-arylbenzothiazoles

Water was successfully employed as a reaction medium in palladium-catalyzed C-H cyclization of thiobenzanilides. Reactions efficiently proceeded under considerably mild conditions such as 40 °C in water, providing a more practical, greener method for the synthesis of 2-arylbenzothiazoles. For some substrates, the addition of an amphiphilic surfactant greatly enhanced the process. The method represents a rare example of palladium-catalyzed C-H functionalization processes performed in water. Georg Thieme Verlag Stuttgart · New York.

Palladium-catalyzed synthesis of 2-substituted benzothiazoles via a C-H functionalization/intramolecular C-S bond formation process

(Chemical Equation Presented) Catalytic synthesis of 2-substituted benzothiazoles from thiobenzanilides was achieved in the presence of a palladium catalyst through C-H functionalization/C-S bond formation. This method features the use of a novel catalytic system consisting of 10 mol % of Pd(II), 50 mol % of Cu(I), and 2 equiv of Bu4NBr that produced variously substituted benzothiazoles in high yields with good functional group tolerance.

One-pot preparation of 2 (alkly)arylbenzothiazoles from the corresponding o-halobenzanilides

Thionation of o-halobenzanilides was carried out in the presence of Lawesson's reagent. Subsequently, the formed thioamides reacted with cesium carbonate to give the corresponding benzothiazole derivatives in the same pot. Georg Thieme Verlag Stuttgart.

Synthesis of 2-substituted benzothiazoles from 2-fluorophenylisothiocyanate

Treatment of 2-fluorophenylisothiocyanate with a Grignard reagent, followed by base-induced cyclization of the resulting thioamide, provides a convenient method of synthesizing 2-substituted benzothiazoles. Best results are obtained upon isolation and purification of the intermediate thioamide, but a direct one-pot isothiocyanate-to-benzothiazole transformation has also been achieved.