68867-19-6Relevant articles and documents
Recyclable copper-catalyzed cyclization of o-haloanilides and metal sulfides: An efficient and practical access to substituted benzothiazoles
Cai, Mingzhong,Hao, Wenyan,Huang, Wencheng,Ye, Qian
, (2022/01/19)
An efficient heterogeneous copper-catalyzed cyclization of o-haloanilides and metal sulfides has been achieved via the C–S coupling in DMF at 80 or 140 °C in the existence of an MCM-41-bound NHC-Cu(I) catalyst and then intramolecular condensation, delivering a wide range of substituted benzothiazoles in mostly good to high yields. This new MCM-41-NHC-CuI complex can facilely be obtained by a two-step procedure starting from easily accessible and inexpensive reagents and reused more than seven times without any significant loss of its catalytic efficiency. The present protocol has been successfully applied to the gram-scale synthesis of two antitumor agents 5F203 and PMX 610.
Design, synthesis and photophysical studies of styryl-based push-pull fluorophores with remarkable solvatofluorochromism
Safir Filho, Mauro,Fiorucci, Sebastien,Martin, Anthony R.,Benhida, Rachid
, p. 13760 - 13772 (2017/11/27)
A library of 20 styryl-based push-pull dyes derived from 6-amino substituted benzothiazoles were prepared by an efficient and practical synthetic route from low-cost starting materials. The dyes were firstly designed to present an effective anchoring site for subsequent conjugation. A series of aryl scaffolds, from substituted phenyl rings containing electron donating and withdrawing groups to polycyclic aromatic derivatives, were screened. The inductive effect of N-alkyl substituted benzothiazoles was also explored for three different arrangements. The investigation of the structure-photophysics relationship was performed by UV-vis absorption and steady-state fluorescence emission measurements in solution and by TD-DFT calculations. The dyes presented high brightness, absorption bands in the visible range (~370-453 nm) and large solvatofluorochromism comprising all the visible spectrum, as a consequence of the strong intramolecular charge transfer (ICT) nature of their excited state.
Efficient and economical access to substituted benzothiazoles: Copper-catalyzed coupling of 2-haloanilides with metal sulfides and subsequent condensation
Ma, Dawei,Xue, Peng,Jiang, Yongwen,Xie, Siwei,Zhang, Xiaojing,Dong, Jinhua
supporting information; experimental part, p. 4222 - 4225 (2009/11/30)
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