33682-61-0Relevant articles and documents
Regioselective N-Functionalization of Tautomerizable Heterocycles through Methyl Trifluoromethanesulfonate-Catalyzed Substitution of Alcohols and Alkyl Group Migrations
Biswas, Srijit,Biswas, Subrata,Duari, Surajit,Elsharif, Asma M.,Maity, Srabani,Mishra, Abhishek Kumar,Morgon, Nelson H.,Roy, Arnab,de Souza, Aguinaldo R.
supporting information, (2022/01/20)
A catalytic synthetic strategy has been developed combining two protocols, such as, direct nucleophilic substitution of alcohols followed by X- to N- alkyl group migration (X=O, S) to access N-functionalized benzoxazolones, benzothiazolethiones, indolinone, benzoimidazolethiones, and pyridinones derivatives. Methyl trifluoromethanesulfonate (MeOTf) was found to catalyze the reaction, which revealed the catalytic property of MeOTf. A mechanism was established through experiments as well as DFT calculations wherein the ?OH group of alcohols were converted to the corresponding ?OMe groups and in situ generated TfOH. The ?OMe groups produced underwent TfOH catalyzed ?X alkylation (X=O, S) of the heterocycles followed by ?X- to ?N-alkyl group migrations in a single step. (Figure presented.).
A catalyst-free and additive-free method for the synthesis of benzothiazolethiones from: O -iodoanilines, DMSO and potassium sulfide
Zhu, Xiaoming,Li, Wenguang,Luo, Xiai,Deng, Guobo,Liang, Yun,Liu, Jianbing
supporting information, p. 1970 - 1974 (2018/05/23)
Under catalyst-free and additive-free conditions, a novel, convenient, eco-friendly method for the synthesis of benzothiazolethiones has been developed. The three-component reaction of o-iodoanilines and K2S with DMSO proceeded smoothly and the corresponding benzothiazolethiones were obtained with good isolated yields. Meanwhile, this method could be used for the synthesis of thioureas from primary diamines. Furthermore, mechanism research showed that DMSO not only functioned as a carbon source, but also as a mild oxidant in this reaction.
ACTIVATION OF NITROSO GROUP WITH THIOLS. A NEW TRANSFORMATION OF PRIMARY AMINES TO ORGANIC SULFIDES OR THIOLS
Ueno, Yoshio,Tanaka, Chie,Okawara, Makoto
, p. 2675 - 2678 (2007/10/02)
Aliphatic primary amines reacted with 2-mercaptobenzothiazole in the presence of t-butylnitrite at room temperature to give condensation products, 2-(alkylthio)benzothiazole.
