5398-35-6Relevant articles and documents
Switchable and Scalable Heteroarylation of Primary Amines with 2-Chlorobenzothiazoles under Transition-Metal-Free and Solvent-Free Conditions
Cheng, Hua,Zhu, Yan-Qiu,Liu, Peng-Fei,Yang, Kai-Qiang,Yan, Jin,Sang, Wei,Tang, Xiao-Sheng,Zhang, Rui,Chen, Cheng
, p. 10288 - 10302 (2021/08/16)
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.
"on Water" Promoted Ullmann-Type C-N Bond-Forming Reactions: Application to Carbazole Alkaloids by Selective N-Arylation of Aminophenols
Chakraborti, Gargi,Paladhi, Sushovan,Mandal, Tirtha,Dash, Jyotirmayee
, p. 7347 - 7359 (2018/07/29)
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.
A practical synthesis of 2-aminobenzothiazoles via copper(I)-catalyzed tandem reaction of 2-iodoanilines with isothiocyanates in ionic liquids
Chen, Ling,Huang, Bin,Nie, Quan,Cai, Mingzhong
, p. 446 - 450 (2016/05/19)
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.
