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.
Facile syntheses of 3-trifluoromethylthio substituted thioflavones and benzothiophenes via the radical cyclization
Wang, Lu,Wang, Huaiyu,Meng, Weidong,Xu, Xiu-Hua,Huang, Yangen
supporting information, p. 389 - 392 (2020/03/04)
3-CF3S substituted thioflavones and benzothiophenes were achieved via the reactions of AgSCF3 with methylthiolated alkynones and alkynylthioanisoles, respectively, promoted by persulfate. This protocol possesses good functional group tolerance and high yields. Mechanistic studies suggested that a classic two-step radical process was involved, which includes addition of CF3S radical to triple bond and cyclization with SMe moiety.
Aerobic Dehydrogenation of N-Heterocycles with Grubbs Catalyst: Its Application to Assisted-Tandem Catalysis to Construct N-Containing Fused Heteroarenes
Kawauchi, Daichi,Noda, Kenta,Komatsu, Yoshiyuki,Yoshida, Kei,Ueda, Hirofumi,Tokuyama, Hidetoshi
supporting information, p. 15793 - 15798 (2020/10/12)
An aerobic dehydrogenation of nitrogen-containing heterocycles catalyzed by Grubbs catalyst is developed. The reaction is applicable to various nitrogen-containing heterocycles. The exceptionally high functional group compatibility of this method was confirmed by the oxidation of an unprotected dihydroindolactam V to indolactam V. Furthermore, by taking advantage of the oxygen-mediated structural change of the Grubbs catalyst, we integrated ring-closing metathesis and subsequent aerobic dehydrogenation to develop the novel assisted-tandem catalysis using molecular oxygen as a chemical trigger. The utility of the assisted-tandem catalysis was demonstrated by the concise synthesis of N-containing fused heteroarenes including a natural antibiotic, pyocyanine.
