156086-03-2

Upstream product

• 860521-22-8 1-benzoylamino-2-benzoylmercapto-4,5-dimethoxy-benzene 
• 127-09-3 sodium acetate 
• 64-19-7 acetic acid 
• 98-88-4 benzoyl chloride 
• 3395-03-7 4,5-dimethoxy-1,2-dinitrobenzene 
• 58249-73-3 bis-(4,5-dimethoxy-2-nitro-phenyl)-disulfane 
• 804476-56-0 N-(2,4,5-trimethoxyphenyl)thiobenzamide 
• 100601-30-7 2-amino-4,5-dimethoxy-thiophenol 
• 100-52-7 benzaldehyde 
• 6315-89-5 3,4-dimethoxyaniline 
• 100-46-9 benzylamine 
• 103-82-2 phenylacetic acid 
• 39078-05-2 N-(3,4-dimethoxyphenyl)benzamide 
• 26510-91-8 2,4,5-trimethoxyaniline 

Downstream Products

• 855281-01-5 2-phenyl-benzothiazole-5,6-diol 

Relevant academic research and scientific papers

NH4I-promoted oxidative formation of benzothiazoles and thiazoles from arylacetic acids and phenylalanines with elemental sulfur

A NH4I/K3PO4-based catalytic system has been established to enable oxidative formation of thiazole compounds from arylacetic acids and phenylalanines with elemental sulfur. While the three-component reaction of anilines or β-naphthylamines with arylacetic acids and elemental sulfur affords benzo[2,1-d]thiazoles and naphtho[2,1-d]thiazoles, the annulation of phenylalanines with elemental sulfur produces 2-benzyl and 2-benzoylthiazoles. This work well complements previous three-component annulations of benzothiazoles from other coupling partners.

Iron-Catalyzed Regioselective Synthesis of 2-Arylbenzoxazoles and 2-Arylbenzothiazoles via Alternative Reaction Pathways

A one-pot regioselective method for the preparation of 2-arylbenzoxazoles from N-arylbenzamides has been developed using iron(III)-catalyzed bromination of the aryl ring, followed by copper(I)-catalyzed O-cyclization with the benzamide side chain. In contrast, reaction of N-arylthiobenzamides with N-bromosuccinimide and iron triflimide led directly to the isolation of the corresponding 2-arylbenzothiazoles via intramolecular C–S bond formation. Mechanistic and control experiments suggest that in this case, bromination occurs at the sulfur atom, resulting in a reactive intermediate that can undergo electrophilic aromatic substitution and S-cyclization. The scope of both processes was explored yielding a range of structural analogues, including a pharmaceutically active compound for the treatment of Duchenne muscular dystrophy and an affinity agent of the amyloid-beta protein in Alzheimer's disease.

Synthesis method of 2-substituted benzothiazole compound under catalyst-free and additive-free conditions

The invention discloses a synthesis method of 2-substituted benzothiazole compound under catalyst-free and additive-free conditions The synthesis method comprises the following steps: adding an aromatic amine compound, a benzylamine compound, an inorganic sulfur source and a solvent into a reaction tube, carrying out a stirring reaction at 130-150 DEG C, cooling the reaction product to room temperature after the reaction is finished, separating and purifying the product to obtain the 2-substituted benzothiazole compound, wherin gram-level experiment scale with good yield can be achieved through the reaction. According to the reaction, the aromatic amine compound and the benzylamine compound are used as substrates to synthesize the 2-substituted benzothiazole compound, no catalyst or additive is needed, reaction conditions are relatively mild, and the 2-substituted benzothiazole compound has high functional group tolerance. The invention develops a method for synthesizing the 2-substituted benzothiazole compound with good or extremely high yield by simple and direct operation and atom economy through multi-component reaction.

Copper-Catalyzed Aerobic Oxidation of Amines to Benzothiazoles via Cross Coupling of Amines and Arene Thiolation Sequence

A one-pot three-component synthesis of benzothiazoles has been developed using the copper-catalyzed aerobic cross coupling of amines followed by arene thiolation using elemental sulfur. The dual roles of elemental sulfur and CuCl(OH)-TMEDA in the aerobic amine oxidation and the aniline thiolation enable the facile access to benzothiazole derivatives from readily available starting materials. The operational simplicity of the current promiscuous catalyst system suggests the high synthetic potential in the preparation of heterocyclic compounds. (Figure presented.).

Assembly of 2-Arylbenzothiazoles through Three-Component Oxidative Annulation under Transition-Metal-Free Conditions

Highly efficient methods for the synthesis of 2-arylbenzothiazoles and 2-arylnaphtho[2,1-d]thiazoles have been developed. Readily available aromatic amines, benzaldehydes, and elemental sulfur were directly assembled through oxidative annulation and C-H f

Thermally induced cyclization of electron-rich N-arylthiobenzamides to benzothiazoles

Heating N-(2-methoxyphenyl)benzenecarbothioamides in refluxing nitrobenzene for 24 hours gives the corresponding benzothiazoles with intramolecular ipso substitution of the ortho-methoxy substituent. The thermal cyclization of various other N-arylthiobenzamides is also explored. Georg Thieme Verlag Stuttgart · New York.

Microwave-assisted one-pot synthesis of benzothiazole and benzoxazole libraries as analgesic agents

Microwave-assisted synthesis of benzothiazole and benzoxazole libraries via PIFA promoted cyclocondensation of 2-aminothiophenols/2-aminophenols with aldehydes under one-pot condition in good to excellent yields was achieved. Twenty compounds have been investigated for their analgesic activity and showed moderate to good activity. Indian Academy of Sciences.

Conversion of thiobenzamides to benzothiazoles via intramolecular cyclization of the aryl radical cation

A new and general method has been developed for the intramolecular cyclization of thiobenzamides to benzothiazoles via aryl radical cations as reactive intermediates. The method utilizes phenyliodine(III) bis(trifluoroacetate) (PIFA) in trifluoroethanol or cerium ammonium nitrate (CAN) in aqueous acetonitrile at room temperature to effect cyclization within 30 min in moderate yields.

Iodine-mediated cyclisation of thiobenzamides to produce benzothiazoles and benzoxazoles

Synthesis of benzothiazoles by reaction of iodine with thiobenzamides, which do not possess an ortho alkoxy or ester group, is described. The unlikely synthesis of benzoxazoles from reaction of 2-alkoxythiobenzamides with iodine is also reported.

Synthesis of benzothiazoles via ipso substitution of ortho- methoxythiobenzamides

An efficient route to the synthesis of benzothiazoles from orthoo-methoxythiobenzamides via the ipso substitution of an aromatic methoxy group is presented, and the mechanism of the Jacobson synthesis of benzothiazoles is further investigated.