25717-41-3Relevant academic research and scientific papers
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)
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.
Benzothiazolyl derivatives
-
Page 12, (2008/06/13)
The present invention relates to compounds of formula (I) wherein R1, R2, R3°R3a and R3b are as provided in the description, and pharmaceutically acceptable salts thereof, for use in the treatment and
