152355-90-3

Upstream product

• 137-07-5 2-amino-benzenethiol 
• 499-06-9 3,5-dimethylbenzoic acid 
• 2516-40-7 2-bromo-1,3-benzothiazole 
• 172975-69-8 3,5-dimethylphenyl boronic acid 
• 50535-17-6 2-deuterioaniline 
• 6613-44-1 3,5-dimethylbenzoyl chloride 
• 1351438-40-8 N-(2-deuterium phenyl)-3,5-dimethylbenzothiozamide 
• 108-67-8 1,3,5-trimethyl-benzene 
• 95-16-9 1,3-Benzothiazole 
• 5779-95-3 3,5-dimethylbenzaldehyde 
• 615-36-1 2-bromoaniline 
• 556-96-7 5-bromo-1,3-xylene 
• 1070731-22-4 3,5-dimethylphenyl methanesulfonate 
• 22445-41-6 3,5-dimethylphenyl iodide 

Relevant academic research and scientific papers

Development of (quinolinyl)amido-based pincer palladium complexes: A robust and phosphine-free catalyst system for C-H arylation of benzothiazoles

(Quinolinyl)amido-ligated palladium(ii) complexes have been synthesized and applied in the catalytic C-H bond arylation of benzothiazoles. The tridentate ligand precursors R2N-C(O)CH2-(NH)-C9H6N [(R2NNN8-Q)-H; R2N = morpholinyl, Me-N-piperazinyl] and the pincer palladium complexes [κN,κN,κN-{R2N-C(O)CH2-(μ-N)-C9H6N}]PdX [(R2NNN8-Q)PdX {R2N = Et2N, morpholinyl, Me-N-piperazinyl; X = OAc or Cl}] were efficiently synthesized, and characterized by various analytical techniques. The iodo derivative (Et2NNN8-Q)PdI was obtained in excellent yield by the treatment of the complex (Et2NNN8-Q)PdCl with KI. The molecular structures of complexes (Et2NNN8-Q)Pd(OAc) (2a), (Et2NNN8-Q)PdCl (3a) and (Et2NNN8-Q)PdI (4a) were elucidated by X-ray crystallography. Complex 3a was found to be the most efficient catalyst for direct C-H bond arylation of substituted benzothiazoles with diverse aryl iodides using a mild base, K2CO3. The working catalyst system 3a is highly robust and can be recycled and reused several times for the arylation of benzothiazole without loss of catalytic activity. Preliminary mechanistic investigations using controlled studies and kinetic analysis have been performed, which greatly support a molecular mechanism for the arylation.

An efficient aqueous phase synthesis of benzimidazoles/benzothiazoles in the presence of β-cyclodextrin

Benzimidazoles/benzothiazoles were synthesized in water under neutral conditions by the reaction of aromatic aldehydes, o-phenylenediamine/2-amino thiophenol mediated by β-cyclodextrin in high yields. β-Cyclodextrin can be recovered and reused without sig

Direct C-H arylation of benzothiazoles by magnetically separable nano copper ferrite, a recyclable catalyst

Abstract A simple and highly practical method for the direct C-H arylation of benzothiazoles has been developed by using nano copper ferrite as a recyclable catalyst. The CuFe2O4 nano could be recovered and reused without significant loss of catalytic activity.

Visible-Light Carbon Nitride-Catalyzed Aerobic Cyclization of Thiobenzanilides under Ambient Air Conditions

A metal-free heterogeneous photocatalysis has been developed for the synthesis of benzothiazoles via intramolecular C-H functionalization/C-S bond formation of thiobenzanilides by inexpensive graphitic carbon nitride (g-C3N4) under visible-light irradiation. This reaction provides access to a broad range of 2-substituted benzothiazoles in high yields under an air atmosphere at room temperature without addition of a strong base or organic oxidizing reagents. In addition, the catalyst was found to be stable and reusable after five reaction cycles.

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.

METAL COMPLEX CONTAINING AZABENZOTHIAZOLE

Metal complexes containing azabenzothiazole are disclosed, which comprise a new series of ligands containing azabenzothiazole structure. The metal complexes can be used as emitters in the emissive layer of an organic electroluminescent device. The use of

New preparation method of 2-substituted benzothiazole compound

The invention provides a new preparation method of a 2-substituted benzothiazole compound, relating to the field of organic synthesis chemistry. According to the new preparation method, in existence of catalyst, oxidant and additive, methylbenzene or a derivative thereof reacts with o-aminothiophenol through free radial reaction so as to prepare the 2-substituted benzothiazole compound in one step. The new method is an example but not limited and has the beneficial effects that methylbenzene or a derivative thereof and o-aminothiophenol construct a C-S bond and a C-N bond through the free radical method for the first time so as to generate the 2-substituted benzothiazole by coupling reaction in one step, and the new preparation method has advantages that the method is efficient, concise and environmentally friendly, raw materials are easy to obtain, and the product purity is high and the like, and the method has good application value and research prospects.

Copper-Catalyzed Arylation of Benzothiazoles with Toluene Derivatives: Synthesis of 2-Arylbenzothiazole

A copper-catalyzed reaction of benzothiazole and readily available toluene derivatives has been disclosed. This protocol is proposed to proceed through the oxidation of toluene and ring opening of benzothiazole, thus providing a new pathway for the synthesis of 2-arylbenzothiazoles..

Mechanistic Insights into Pincer-Ligated Palladium-Catalyzed Arylation of Azoles with Aryl Iodides: Evidence of a PdII-PdIV-PdII Pathway

Pincer-based (R2POCNR′2)PdCl complexes along with CuI cocatalyst catalyze the arylation of azoles with aryl iodides to give the 2-arylated azole products. Herein, we report an extensive mechanistic investigation for the direct arylation of azoles involving a well-defined and highly efficient (iPr2POCNEt2)PdCl (2a) catalyst, which emphasizes a rare PdII-PdIV-PdII redox catalytic pathway. Kinetic studies and deuterium labeling experiments indicate that the C-H bond cleavage on azoles occurs via two distinct routes in a reversible manner. Controlled reactivity of the catalyst 2a underlines the iodo derivative (iPr2POCNEt2)PdI (3a) to be the resting state of the catalyst. The intermediate species (iPr2POCNEt2)Pd-benzothiazolyl (4a) has been isolated and structurally characterized. A determination of reaction rates of compound 4a with electronically different aryl iodides has revealed the kinetic significance of the oxidative addition of the C(sp2)-X electrophile, aryl iodide, to complex 4a. Furthermore, the reactivity behavior of 4a suggests that the arylation of benzothiazole proceeds via an oxidative addition/reductive elimination pathway involving a (iPr2POCNEt2)PdIV(benzothiazolyl)(Ar)I species, which is strongly supported by DFT calculations.

Microwave assisted aqueous phase synthesis of benzothiazoles and benzimidazoles in the presence of Ag2O

A simple and high yielding method for synthesized benzothiazoles and benzimidazole in water under micro wave irradiation by the reaction of 2-amino thiophenol and o-phenylenediamine with various aromatic aldehydes in the presence of Ag2O. Agsu