25717-12-8Relevant 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.
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
Nahakpam, Lokendrajit,Chingakham, Brajakishor S.,Laitonjam, Warjeet S.
, p. 267 - 272 (2015/01/30)
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
Postsynthetic modification of IRMOF-3 with a copper iminopyridine complex as heterogeneous catalyst for the synthesis of 2-aminobenzothiazoles
Liu, Jie,Zhang, Xiaobin,Yang, Jin,Wang, Lei
, p. 198 - 203 (2014/03/21)
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