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Upstream product

• 137-07-5 2-amino-benzenethiol 
• 2293-07-4 1-(4-methoxyphenyl)thiourea 
• 13519-16-9 N-(4-methoxyphenyl)cyanamide 
• 501076-56-8 C₁₄H₁₄N₂OS₂ 
• 13037-60-0 1-bromo-2-isothiocyanatobenzene 
• 104-94-9 4-methoxy-aniline 
• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 24045-02-1 (benzothiazole-2-sulfonyl)-acetic acid ethyl ester 
• 100-52-7 benzaldehyde 
• 2284-20-0 4-Methoxyphenyl isothiocyanate 
• 14223-47-3 4-methoxyphenyl isoselenocyanate 
• 615-36-1 2-bromoaniline 
• 67616-74-4 1-(2-bromophenyl)-3-(4-methoxyphenyl)thiourea 
• 615-43-0 2-iodophenylamine 

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.

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.

"on Water" Promoted Ullmann-Type C-N Bond-Forming Reactions: Application to Carbazole Alkaloids by Selective N-Arylation of Aminophenols

The Ullmann-type cross coupling of a variety of aromatic, aliphatic amines with aryl halides is reported using a CuI-based catalytic system in combination with an easily accessible prolinamide ligand in aqueous media. The method is mild and tolerant to air, moisture, and a wide range of functional groups, providing a novel way to access a variety of aminated products. Secondary amines like heteroaromatic amines and nucleobases have also been used, affording the corresponding coupling products in good to excellent yields. Moreover, this method has been employed for chemoselective C-N arylation of aminophenols and further utilized for the synthesis of carbazole natural products, avoiding the protection and deprotection steps.

Iodine-catalyzed formation of substituted 2-aminobenzothiazole derivatives in PEG400

An iodine-catalyzed formation of substituted 2-aminobenzothiazole derivatives is herein described using hydrogen peroxide as an oxidant in PEG400. The method enabled an efficient environmentally sound access to this valuable scaffold in moderate to excellent yields under metal-free conditions.

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.

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

Dithiocarbamate promoted practical synthesis of N-Aryl-2-aminobenzazoles: Synthesis of novel Aurora-A kinase inhibitor

Various N-aryl-2-aminobenzoxazoles and N-aryl-2-aminobenzothiazoles were synthesized from o-aminophenol and o-aminothiophenol, respectively, mediated by dithiocarbamate in one step. The salient features of this method include mild reaction condition, high

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.

Ligand- and solvent-free synthesis of 2-aminobenzothiazoles by copper-catalyzed tandem reaction of 2-haloanilines with isothiocyanates

We report an environmentally friendly, efficient and practical method for the synthesis of 2-aminobenzothiazoles by a copper(II)-catalyzed tandem reaction of 2-haloanilines with isothiocyanates under ligand- and solvent-free conditions in air. The developed methodology conforms to the principles of 'green chemistry' and addresses the shortage of such methods for the synthesis of 2-aminobenzothiazoles. The reaction is quite general and generates a variety of 2-aminobenzothiazoles in good to excellent yields. Copyright