175694-99-2Relevant articles and documents
Ionic Reactivity of 2-Isocyanoaryl Thioethers: Access to 2-Halo and 2-Aminobenzothia/Selenazoles
Bao, Lan,Dong, Jinhuan,Hu, Junlin,Jia, Mengying,Liu, Xiaoli,Sun, Shaoguang,Xu, Xianxiu
, (2022/02/23)
An ionic cascade insertion/cyclization reaction of thia-/selena-functionalized arylisocyanides has been successfully developed for the efficient and practical synthesis of 2-halobenzothiazole/benzoselenazole derivatives. This synthetic protocol, incorporating a halogen atom when forming the five-membered ring of benzothia/selenazoles, is different from the existing ones, where halogenation of the preformed benzothia/selenazole precursors happens. Additionally, a facile access to 2-aminobenzothiazoles is also achieved by the one-pot cascade reaction of 2-isocyanoaryl thioethers, iodine, and amines.
4CzIPN-tBu-Catalyzed Proton-Coupled Electron Transfer for Photosynthesis of Phosphorylated N-Heteroaromatics
Liu, Yan,Chen, Xiao-Lan,Li, Xiao-Yun,Zhu, Shan-Shan,Li, Shi-Jun,Song, Yan,Qu, Ling-Bo,Yu, Bing
supporting information, p. 964 - 972 (2021/01/12)
2,4,5,6-Tetrakis(3,6-di-tert-butyl-9H-carbazol-9-yl)isophthalonitrile (4CzIPN-tBu) was developed as a photocatalyst for the phosphorus-radical-initiated cascade cyclization reaction of isocyanides. By using 4CzIPN-tBu as catalyst, we developed a visible-light-induced proton-coupled electron transfer strategy for the generation of phosphorus-centered radicals, via which a wide range of phosphorylated phenanthridines, quinolines, and benzothiazoles were successfully constructed.
Metal-free photo-induced radical C-P and C-S bond formation for the synthesis of 2-phosphoryl benzothiazoles
Yang, Wenchao,Li, Bing,Zhang, Mingming,Wang, Shuang,Ji, Yigang,Dong, Sa,Feng, Jianguo,Yuan, Shuzhong
supporting information, p. 1313 - 1316 (2019/11/28)
We reveal here a visible-light promoted phosphorylation of 2-isocyanoaryl thioethers for the first time with concomitant C(sp3)-S bond cleavage and imidoyl C–S formation. Additionally, this method features the use of 3 mol% organic dye Rose Bengal as the photocatalyst without external transition-metal or peroxide oxidants, and provides a novel and environmentally friendly approach for the preparation of a variety of 2-phosphoryl benzothiazoles in moderate to good yields.
Visible-light-induced radical cascade cyclization of oxime esters and aryl isonitriles: Synthesis of cyclopenta[: B] quinoxalines
Yuan, Yao,Dong, Wu-Heng,Gao, Xiao-Shuang,Xie, Xiao-Min,Zhang, Zhao-Guo
supporting information, p. 11900 - 11903 (2019/10/11)
A visible-light-induced radical cascade cyclization of aryl isonitriles and cyclobutanone oxime esters for the synthesis of cyclopenta[b]quinoxalines has been accomplished for the first time. The key to the success of this process was the integration of the in situ-formed nitrile radical followed by the cascade radical isonitrile/nitrile insertion-cyclization. The easy introduction of substituents for both substrates and the high functional group tolerance of the reaction make it an efficient strategy to give various quinoxaline derivatives in moderate to good yields.
Cascade C(sp3)-S Bond Cleavage and Imidoyl C-S Formation: Radical Cyclization of 2-Isocyanoaryl Thioethers toward 2-Substituted Benzothiazoles
Yang, Wen-Chao,Wei, Kai,Sun, Xue,Zhu, Jie,Wu, Lei
supporting information, p. 3144 - 3147 (2018/05/28)
A cascade radical cyclization of 2-isocyanoaryl thioethers with H-phosphorus oxides, organoboronic acids, or alkyl radical precursors has been efficiently developed, providing a novel and highly efficient methodology to structurally diverse C2-substituted benzothiazole derivatives with broad functional group tolerance and good yields. This cascade radical process achieves the first cycloaddition of an imidoyl radical from isocyanide to sulfur atom, rending C(sp2)-S bond formation.
Studies on isocyanides. 2-Isocyanothioanisole, a synthetic equivalent of the benzothiazol-2-YL anion
Bossio, Ricardo,Marcaccini, Stefano,Pepino, Roberto,Torroba, Tomas
, p. 471 - 474 (2007/10/03)
A synthesis of 2-isocyanothioanisole (3) is described. The reaction between 3 and electrophilic reagents took place easily to give 2-functionalized benzothiazoles (6).
