6276-78-4

Usage

InChI:InChI=1/C13H9ClN2S/c14-9-5-7-10(8-6-9)15-13-16-11-3-1-2-4-12(11)17-13/h1-8H,(H,15,16)

Upstream product

• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 106-47-8 4-chloro-aniline 
• 7392-67-8 1-(4-chlorophenyl)-3-phenylthiourea 
• 615-43-0 2-iodophenylamine 
• 2131-55-7 4-Chlorophenyl isothiocyanate 
• 14223-48-4 p-chlorophenyl isoselenocyanate 
• 137-07-5 2-amino-benzenethiol 
• 615-36-1 2-bromoaniline 
• 894949-65-6 C₁₃H₁₀ClIN₂S 
• 38985-64-7 o-fluorophenyl isothiocyanate 
• 65551-02-2 1-o-Fluorphenyl-3-p-chlorphenyl-2-thiocarbamid 
• 88-74-4 2-nitro-aniline 
• 1218906-35-4 N-(4-chlorophenyl)-N-(2-iodophenyl)methanediimine 
• 75-15-0 carbon disulfide 

Downstream Products

• 65416-75-3 (4-chloro-phenyl)-(3-methyl-3H-benzothiazol-2-ylidene)-amine 

Relevant academic research and scientific papers

Switchable and Scalable Heteroarylation of Primary Amines with 2-Chlorobenzothiazoles under Transition-Metal-Free and Solvent-Free Conditions

2-Aminobenzothiazoles comprise a valuable structural motif, which prevails in versatile natural products and biologically active compounds. Herein, a switchable and scalable C-N coupling protocol was developed for the synthesis of these compounds from 2-chlorobenzothiazoles and primary amines. Gratifyingly, this protocol was achieved under transition-metal-free and solvent-free conditions. Moreover, introducing an appropriate amount of NaH completely switched the selectivity from mono- toward di-heteroarylation, and further investigations provided a rationale for this new finding. Furthermore, gram-scale synthesis of representative products 3a and 4a was realized by applying operationally simple and glovebox-free procedures, which revealed the practical usefulness of this work. Finally, evaluation of the quantitative green metrics provided evidence that our protocol was superior over the literature ones in terms of green chemistry and sustainability.

Environment-friendly and efficient synthesis of 2-aminobenzo-xazoles and 2-aminobenzothiazoles catalyzed by: Vitreoscilla hemoglobin incorporating a cobalt porphyrin cofactor

In this study, an environment-friendly and efficient artificial Vitreoscilla hemoglobin (VHb) for the synthesis of 2-aminobenzoxazoles and 2-aminobenzothiazoles has been reported. We demonstrate an expression-based porphyrin substitution strategy to produce VHb containing cobalt porphyrin instead of native hemin, which can catalyze the oxidative cyclization of corresponding 2-aminobenzoxazoles and 2-aminobenthiazoles with up to 97% yield and 4850 catalytic turnovers in water under aerobic conditions. Hence, we provide a green and mild method for the synthesis of 2-aminobenzoxazoles and 2-aminobenzothiazoles. In addition, we indicate the value of porphyrin ligand substitution as a strategy to tune and enhance the catalytic properties of hemoproteins in non-natural reactions.

Electrochemical NaI/NaCl-mediated one-pot synthesis of 2-aminobenzoxazoles in aqueous mediaviatandem addition-cyclization

An electrochemical synthesis of 2-aminobenzoxazoles from 2-aminophenols and isothiocyanates was successfully developed in a one-pot fashion. Using inexpensive and widely available NaI and NaCl co-operatively in catalytic amounts, our electrosynthesis approach provided various 2-aminobenzoxazole products in moderate to high yields in an open-flask type undivided cell without using any external supporting electrolyte and base. The protocol can be applied to the synthesis of 2-aminobenzothiazoles from the corresponding 2-thiophenols in moderate yields. This protocol has many benefits. It is metal-free and highly scalable and uses inexpensive mediators and EtOH/water as an environmentally friendly solvent under mild conditions.

Synthesis of Benz-Fused Azoles via C-Heteroatom Coupling Reactions Catalyzed by Cu(I) in the Presence of Glycosyltriazole Ligands

Glycosyl triazoles are conveniently accessible and contain multiple metal-binding units that may assist in metal-mediated catalysis. Azide derivatives of d-glucose have been converted to their respective aryltriazoles and screened as ligands for the synthesis of 2-substituted benz-fused azoles and benzimidazoquinazolinones by Cu-catalyzed intramolecular Ullmann type C-heteroatom coupling. Good to excellent yields for a variety of benz-fused heterocyles were obtained for this readily accessible catalytic system.

Synergism of fused bicyclic 2-aminothiazolyl compounds with polymyxin B against: Klebsiella pneumoniae

A series of fused bicyclic 2-aminothiazolyl compounds were synthesized and evaluated for their synergistic effects with polymyxin B (PB) against Klebsiella pneumoniae (SIPI-KPN-1712). Some of the synthesized compounds exhibited synergistic activity. When 4 μg ml-1 compound B1 was combined with PB, it showed potent antibacterial activity, achieving 64-fold reduction of the MIC of PB. Furthermore, compound B1 showed prominent synergistic efficacy in both concentration gradient and time-kill curves in vitro. In addition, B1 combined with PB also exhibited synergistic and partial synergistic effect against E. coli (ATCC25922 and its clinical isolates), Acinetobacter baumannii (ATCC19606 and its clinical isolates), and Pseudomonas aeruginosa (Pae-1399).

A practical synthesis of 2-aminobenzothiazoles via copper(I)-catalyzed tandem reaction of 2-iodoanilines with isothiocyanates in ionic liquids

A copper(I)-catalyzed tandem reaction of 2-iodoanilines with isothiocyanates was achieved in hydrophobic [bmim][PF6] ionic liquid under mild conditions, generating a variety of 2-aminobenzothiazoles in good to excellent yields. The tandem reaction that was carried out in [bmim][PF6] has some obvious advantages such as accelerated reaction rate and increased yield as compared with the reaction run in volatile solvents such as toluene. Furthermore, the CuI/1,10-phenanthroline catalytic system can be reused up to eight times without loss of activity and efficiency.

A Synthesis of Benzothiazoles and Indoles by Direct C(sp2)-I Activation Catalyzed by Copper(II) on Silica-Coated Magnetite Nanoparticles

N-Substituted 2-amino-1,3-benzothiazoles and 2,3-disubstituted indoles were prepared by C-S and C-C cross-coupling reactions of 2-iodoanilines with isothiocyanates or 1,3-dicarbonyl compounds, respectively, in the presence of magnetic nanoparticles functionalized with a copper(II)-Schiff base complex as an efficient and reusable catalyst.

Oxidative coupling of formamides with β-dicarbonyl compounds and the synthesis of 2-aminobenzothiazole using Cu(II)-functionalized Fe3O4 nanoparticles This article is dedicated to memory of Mostafa Chamran.

The Fe3O4@EDTA-Cu(II) nanoparticles catalyzed oxidative coupling of formamides with β-dicarbonyl compounds is developed using tert-butyl hydroperoxide as an oxidant. In general, the enol carbamates are synthesized in excellent yields (up to 92%) under the optimized reaction conditions. Fe3O4@EDTA-Cu(II) has the advantage of being magnetically recoverable. Also, we have established a highly efficient Fe3O4@EDTA-Cu(II)-catalyzed tandem reaction of 2-iodoanilines with isothiocyanates for the synthesis of 2-aminobenzothiazoles.

Polymer-supported tribromide as a new solid phase and recyclable catalyst for the synthesis of 2-(n-arylamino)benzothiazoles under solvent-free microwave irradiation conditions

The solid-phase synthesis of 2-(N-arylamino)benzothiazoles is achieved by reacting substituted thioureas with polymer-supported tribromide. A series of 2-(N-aryl)aminobenzothiazoles is prepared in high yields under microwave irradiation. The method has se

Gold nanoparticle catalyzed intramolecular C-S bond formation/C-H bond functionalization/cyclization cascades

An efficient synthesis of 2-(N-aryl)aminobenzo[d]-1,3-thiazoles via intramolecular C-S bond formation/C-H bond functionalization utilizing an unusual cocatalytic Au-NPs/KMnO4 system under an oxygen atmosphere at 80 °C is presented. Au-NPs can b