137-07-5Relevant articles and documents
Synthesis of 2H-1,4-benzothiazin-3(4H)-ones and 2H-1,4-benzoselenazin-3(4H)-ones with the aid of samarium(II) iodide
Zhong, Weihui,Zhang, Yongmin
, p. 3125 - 3127 (2001)
Bis(o-nitrophenyl) disulfides or diselenides were easy to reduce by samarium(II) iodide to produce the active intermediates 2 in situ, which readily react with α-halocarboxylic derivatives to yield the corresponding products 2H-1,4-benzothiazin-3(4H)-ones and 2H-1,4-benzoselenazin-3(4H)-ones, respectively, in moderate to high yields under mild conditions.
Iodine mediated oxidative cross-coupling of unprotected anilines and heteroarylation of benzothiazoles with 2-methylquinoline
Rahim, Abdul,Shaik, Siddiq Pasha,Baig, Mirza Feroz,Alarifi, Abdullah,Kamal, Ahmed
, p. 635 - 644 (2018)
Iodine-promoted oxidative C-H/C-H cross-coupling of unprotected anilines and 2-methylquinoline to furnish C4-carbonylated aniline (4-aminophenyl)(quinoline-2-yl) methanones in moderate to good yields has been demonstrated. This work provides the first site-selective approach for the synthesis of free amino groups containing methanones including unprecedented C-H functionalization rather than the N-H functionalization of unprotected anilines via the Kornblum oxidation of 2-methylquinoline. Furthermore, we noticed that the incorporation of KOH under standard conditions provides 2-heteroarylbenzothiazoles from benzothiazoles and 2-methylquinoline in good to excellent yields. These transformations do not require any transition metals or peroxides and tolerate various functional groups such as methoxy, hydroxy, bromo, chloro and nitro groups. Moreover, a plausible mechanistic pathway is proposed.
Novel synthesis of benzothiazole by self-redox tandem reaction of disulfide with aldehyde
Liu, Bo,Zhu, Ning,Hong, Hailong,Han, Limin
, p. 9287 - 9292 (2015)
A novel methodology for the preparation of benzothiazole derivatives via the reaction of ortho-anilino disulfides with aryl and heteroaryl aldehydes catalyzed by Na2S·9H2O has been developed. The reaction mechanism was investigated by LC-MS and 1H NMR. The disulfide was cleaved firstly by the interchange reaction of the disulfide and metal sulfide, and the resulting thiol reacted in situ with the aldehyde to form the corresponding benzothiazoline. Subsequently, the intermediate benzothiazoline reduced the disulfide to thiol and it was oxidized to benzothiazole. The excess benzothiazoline was oxidized by air and both halves of the disulfide were ultimately converted to the desired benzothiazole.
Iodine-catalyzed amination of benzothiazoles with KSeCN in water to access primary 2-aminobenzothiazoles
Chen, Xiran,Fu, Lianrong,Hao, Xin-Qi,Shi, Linlin,Song, Mao-Ping,Zhu, Xinju,Zhu, Yu-Shen
, (2021/09/09)
A facile and sustainable approach for the amination of benzothiazoles with KSeCN using iodine as the catalyst in water has been disclosed under transition-metal free conditions. The reaction proceeded smoothly to afford various primary 2-amino benzothiazoles in up to 96% yield. A series of control experiments were performed, suggesting a ring-opening mechanism was involved via a radical process. This protocol provides efficient synthesis of primary 2-aminobenzothiazoles
Preparation method of o-aminothiophenol
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, (2020/12/30)
The invention provides a preparation method of o-aminothiophenol. The preparation method comprises the following steps: putting o-chloronitrobenzene into sodium methyl mercaptide, and performing heating under the action of a catalyst to carry out a methyl vulcanization reaction so as to prepare o-nitrophenyl dimethyl sulfide; putting o-nitrophenyl thioether into a solvent, and carrying out hydrogenation reduction to prepare o-aminobenzene thioether; and demethylating the o-aminothiophenol under the action of hydrobromic acid to obtain the o-aminothiophenol. The preparation method of o-aminothiophenol has the advantages of high yield and high product purity.