1283595-52-7

Usage

Structure

Benzothiazole derivative with a methylated imidazole ring

Pharmaceutical applications

Potential use in the field of neuroscience and neuropharmacology

Neurotransmitter systems modulation

Ability to modulate GABA and glutamate receptors in the brain

Potential drug candidate

For the treatment of anxiety, epilepsy, and other neurological disorders

Further research needed

To fully understand the therapeutic potential and safety profile of the compound.

Upstream product

• 137-07-5 2-amino-benzenethiol 
• 13750-81-7 N-methyl-2-imidazolcarboxaldehyde 
• 103-72-0 phenyl isothiocyanate 
• 1739-84-0 1,2-dimethyl-1H-imidazole 
• 88-73-3 2-Chloronitrobenzene 
• 616-47-7 1-methyl-1H-imidazole 
• 95-16-9 1,3-Benzothiazole 

Relevant academic research and scientific papers

Nitro-methyl redox coupling: Efficient approach to 2-hetarylbenzothiazoles from 2-halonitroarene, methylhetarene, and elemental sulfur

A simple, straightforward, and atom economic approach to 2-hetarylbenzothiazoles starting from 2-halonitroarene, methylhetarene, and elemental sulfur under mild conditions is described. The method is highlighted by the direct redox nitro-methyl reaction for carbon-nitrogen bond formation without an added oxidizing or reducing agent.

Halo-Bridged Abnormal NHC Palladium(II) Dimer for Catalytic Dehydrogenative Cross-Coupling Reactions of Heteroarenes

This work describes the dehydrogenative coupling of heteroarenes using a dimeric halo-bridged palladium(II) catalyst bearing an abnormal NHC (aNHC) backbone. The catalyst can successfully activate the C-H bond of a wide range of heteroarenes, which include benzothiazole, benzoxazole, thiophene, furan, and N-methylbenzimidazole. Further, it exhibited good activity for heteroarenes bearing various functional groups such as CN, CHO, Me, OMe, OAc, and Cl. Additionally, we isolated the active catalyst by performing stoichiometric reaction and characterized it as the acetato-bridged dimer of (aNHC)PdOAc by single-crystal X-ray study.

Reactions of 2-aminothiophenol with pyridineand imidazolecarboxaldehydes

Reflux of imidazole-2-carboxaldehyde, 1-methylimidazole-2-carboxaldehyde, imidazole4-carboxaldehyde, or 5-bromopyridine-2-carboxaldehyde with 2-aminothiophenol in ethanol in the presence of air oxygen for 1.5 h affords the corresponding 2-hetaryl-substituted 1,3-benzothiazoles. The reaction of 2-(1-methyl-1H-imidazol-2-yl)-1,3-benzothiazole with Cu(ClO4)2?6H2O gives bis[2-(1-methyl-1H-imidazol-2-yl)-1,3-benzothiazole]copper(ii) diperchlorate monohydrate.

Design and Syntheses of Palladium Complexes of NNN/CNN Pincer Ligands: Catalyst for Cross Dehydrogenative Coupling Reaction of Heteroarenes

This report describes simple syntheses of a new class of palladium(II) pincer complexes having NNN and CNN coordination modes. The new complexes were fully characterized with the help of 1H and 13C{1H} NMR, HRMS, and IR sp

Catalyst- and Supporting-Electrolyte-Free Electrosynthesis of Benzothiazoles and Thiazolopyridines in Continuous Flow

A catalyst- and supporting electrolyte-free method for electrochemical dehydrogenative C?S bond formation in continuous flow has been developed. A broad range of N-arylthioamides have been converted to the corresponding benzothiazoles in good to excellent yields and with high current efficiencies. This transformation is achieved using only electricity and laboratory grade solvent, avoiding degassing or the use of inert atmosphere. This work highlights three advantages of electrochemistry in flow, which is (i) a supporting electrolyte-free reaction, (ii) an easy scale-up of the reaction without the need for a larger reactor and, (iii) the important and effective impact of having a good mixing of the reaction mixture, which can be achieved effectively with the use of flow systems. This clearly improves the reported methods for the synthesis of benzothiazoles.

TEMPO-Catalyzed Electrochemical C-H Thiolation: Synthesis of Benzothiazoles and Thiazolopyridines from Thioamides

Benzothiazoles and thiazolopyridines are widely prevalent in pharmaceuticals and organic materials. Herein, we report a metal- and reagent-free method for the uniform synthesis of benzothiazoles and thiazolopyridines through 2,2,6,6-tetramethylpiperidine-N-oxyl radical (TEMPO)-catalyzed electrolytic C-H thiolation. This dehydrogenative coupling process provides access to a host of benzothiazoles and thiazolopyridines from N-(hetero)arylthioamides. Mechanistic studies suggested that the thioamide substrate was oxidized with the electrochemically generated TEMPO+ through an inner-sphere electron transfer to afford a thioamidyl radical, which undergoes homolytic aromatic substitution to form the key C-S bond.

Palladium-catalyzed dehydrogenative cross-couplings of benzazoles with azoles

Different enough: Palladium-catalyzed cross-couplings of benzazoles with imidazoles, oxazoles, and thiazoles furnish unsymmetrical 2,2′- bisheteroaryls in high yield (see scheme). These oxidative Ci-C bond formations use the selective cleavage of the Ci-H bond at C2 in the two coupling partners and are robust enough to be conducted under normal air atmosphere.