6265-91-4Relevant 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.
Graphene oxide-catalyzed synthesis of benzothiazoles with amines and elemental sulfur via oxidative coupling strategy of amines to imines
He, Haiping,Duan, Dehao,Li, Hong,Wei, Yifei,Nie, Liang,Tang, Bo,Wang, Hanyu,Han, Xiaowei,Huang, Panpan,Peng, Xiangjun
, (2022/01/13)
The graphene oxide-catalyzed coupling and cyclization reactions of primary amines with elemental sulfur was developed to afford various optically property benzothiazoles. This coupling and cyclization strategies proceeded under the oxidant system graphene oxide/O2 and constructed carbon-heteroatom (N, S) bonds with amines and elemental sulfur. Due to benzothiazoles as common chromophores, these products exhibited intriguing fluorescence properties, including outstanding Stokes shifts (up to 161 nm) and quantum yields (up to 74%). Utilizing the products’ unique fluorescence response in different solvents, β-naphthothiazole 4a showed excellent aggregation-induced emission properties in 1,2-dichloroethane, which was 60 times higher than in tetrahydrofuran.
Improved, gram-scale synthesis of sildenafil in water using arylacetic acid as the acyl source in the pyrazolo[4,3-d]pyrimidin-7-one ring formation
Laha, Joydev K.,Gulati, Upma,Saima,Gupta, Anjali,Indurthi, Harish Kumar
supporting information, p. 2643 - 2648 (2021/02/16)
An improved, gram-scale synthesis of the blockbuster drug sildenafil, used for the treatment of male erectile dysfunction, has been developed. Unlike the previous literature, the current method demonstrates the use of arylacetic acid as an acyl source, a cheap oxidant K2S2O8, and water as the reaction medium in the key step of pyrrazolo[4,3-d]pyrimidin-7-one ring formation. As well as being a green and benign approach, the current method reduces the cost by half compared to our previous strategy. In addition, the general relevance of the method has been demonstrated in the synthesis of a variety of quinazolinone and benzothiazole derivatives with excellent functional group tolerance.