2501-06-6

Usage

InChI:InChI=1/C13H9N3O2S/c17-16(18)10-7-5-9(6-8-10)14-13-15-11-3-1-2-4-12(11)19-13/h1-8H,(H,14,15)

Upstream product

• 615-43-0 2-iodophenylamine 
• 2131-61-5 p-nitrophenyl isothiocyanate 
• 95-16-9 1,3-Benzothiazole 
• 100-01-6 4-nitro-aniline 
• 75-15-0 carbon disulfide 
• 137-07-5 2-amino-benzenethiol 
• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 136-95-8 2-amino-benzthiazole 
• 586-78-7 para-nitrophenyl bromide 
• 904182-39-4 C₁₃H₁₀IN₃O₂S 
• 636-98-6 p-nitrobenzene iodide 
• 62635-52-3 N-(2-iodo-phenyl)thiourea 
• 5391-30-0 1-(2-bromophenyl)thiourea 
• 615-36-1 2-bromoaniline 

Downstream Products

• 133929-19-8 2-(4-isothiocyanatophenylamino)benzothiazole 
• 5677-17-8 N¹-(benzo[d]thiazol-2-yl)benzene-1,4-diamine 

Relevant academic research and scientific papers

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.

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.

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.

SMALL MOLECULE ACTIVATORS OF NICOTINAMIDE PHOSPHORIBOSYLTRANSFERASE (NAMPT) AND USES THEREOF

Provided herein are small molecule activators of Nicotinamide Phosphoribosyltransferase (NAMPT), compositions comprising the compounds, and methods of using the compounds and compositions.

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.

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.

Base-mediated N- And O-arylations of NH-containing heterocycles, heterocyclic amines and phenols

Nucleophilic substitution reactions of N-heterocycles such as imidazole, benzimidazole, indole and pyrazole as well as NH2 or OH containing heterocycles, with electron-deficient aryl halides in the presence of t-BuOK or K2CO3as base and DMSO as solvent are reported. A series of N-aryl azoles, unsymmetric diaryl ethers and diaryl amines were obtained in good yields.

Straightforward synthesis of 2-anilinobenzoxazoles and -benzothiazoles via mechanochemical ball-milling-promoted one-pot reactions

Under mechanochemical ball-milling and solvent-free conditions, a series of 2-anilinobenzoxazoles and -thiazoles were synthesized directly from the one-pot reaction of anilines, CS2, and 2-aminophenol and -thiophenol. This protocol exhibits the

Postsynthetic modification of IRMOF-3 with a copper iminopyridine complex as heterogeneous catalyst for the synthesis of 2-aminobenzothiazoles

A copper iminopyridine complex has been immobilized on to a metal-organic framework (MOF) through postsynthetic modification of IRMOF-3. The modified MOFs were fully demonstrated by using a variety of methods, and the structural integrity of the modified

Synthesis of N-substituted-2-aminobenzothiazoles using nano copper oxide as a recyclable catalyst under ligand-free conditions, in reusable PEG-400 medium

A simple and practical method for the synthesis of N-substituted-2- aminobenzothiazoles via a cross-coupling reaction of 2-iodo anilines with isothiocyanates is envisaged using nano copper oxide as a recyclable catalyst and Cs2CO3 as a base in PEG-400, as a bio-degradable, reusable, inexpensive and non-toxic reaction medium, under ligand-free conditions. The present tandem process underlines environmental acceptability to access a wide range of N-substituted-2-aminobenzothiazoles in good to excellent yields.