6265-91-4Relevant articles and documents
Synthesis of 2-Arylbenzothiazoles from Nitrobenzenes, Benzylamines, and Elemental Sulfur via Redox Cyclization
Imoto, Mitsutaka,Mizuno, Takumi,Nomoto, Akihiro,Ogawa, Akiya,Takeda, Motonori,Teramoto, Masahiro
supporting information, p. 386 - 390 (2022/03/02)
A sustainable advanced synthetic method was developed based on redox cyclization for the synthesis of 2-arylbenzothiazoles in good to excellent yields from readily available nitrobenzenes, benzylamines, and elemental sulfur without the use of transition-metal catalysts. This method is remarkable: nitro group reduction, a benzylamine redox reaction, sulfuration, condensation, and cyclization, all proceed in a single step to generate a heterocycle. It is also highly atom-economical and does not require any external oxidizing or reducing agents.
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.
Br?nsted Acid Mediated Nucleophilic Functionalization of Amides through Stable Amide C?N Bond Cleavage; One-Step Synthesis of 2-Substituted Benzothiazoles
Biswas, Srijit,Biswas, Subrata,Duari, Surajit,Elsharif, Asma M.,Maity, Srabani,Roy, Arnab
supporting information, p. 3569 - 3572 (2021/07/22)
We have developed a Br?nsted acid mediated synthetic method to directly cleave stable amide C?N bonds by a variety of alcohol and amine nucleophiles. Reverse reactivity was observed and alcoholysis of amides by activated primary and secondary benzylic, and propargylic alcohols have been achieved instead of the expected nucleophilic substitution of alcohols. As an application, 2-substituted benzothiazole derivatives have been synthesized in one pot employing 2-aminothiophenol as nucleophile.