Highly efficient synthesis of novel fluorinated 3-amino-2-mercaptobenzothiazole-2(3H)-thione derivatives

Highly efficient synthesis of novel fluorinated 3-amino-2-mercaptobenzothiazole-2(3H)-thione derivatives Full article

Journal

Journal of Fluorine Chemistry
ISSN: 0022-1139

Output data

Year: 2020, Volume: 239, Article number : 109628, Pages count : DOI: 10.1016/j.jfluchem.2020.109628

Tags

C-F activation; Fluorinated mercaptobenzothiazole derivatives; Fluorinated S,N-heterocycles; Polyfluorinated arylhydrazines; Tandem reaction

Authors

Politanskaya L. ¹ , Bagryanskaya I. ^1,2 , Tretyakov E. ^1,2 , Xi C. ³

Affiliations

1	(Scopus) N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences, Ac. Lavrentiev Ave., 9Novosibirsk 630090, Russian Federation
2	(Scopus) Novosibirsk State University, Pirogova Street, 2Novosibirsk 630090, Russian Federation
3	(Scopus) Key Laboratory of Bioorganic Phosphorus Chemistry&Chemical Biology (Ministry of Education), Departament of Chemistry, Tsinghua University, Beijing, 100084, China

Here, a convenient and efficient method for the synthesis of polyfluorinated 3-amino-2-mercaptobenzothiazole-2(3H)-thione derivatives from the corresponding arylhydrazines and CS2, mediated by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in acetonitrile is described. The reaction proceeded via selective intramolecular ortho-fluorine atom substitution by the S-nucleophilic center of the carbon disulfide molecule attached at the first stage of the reaction (a tandem process). The reaction takes place under mild reaction conditions (room temperature), has an excellent yield, and involves readily available starting materials. © 2020 Elsevier B.V.

Politanskaya L. , Bagryanskaya I. , Tretyakov E. , Xi C.
Highly efficient synthesis of novel fluorinated 3-amino-2-mercaptobenzothiazole-2(3H)-thione derivatives
Journal of Fluorine Chemistry. 2020. V.239. 109628 . DOI: 10.1016/j.jfluchem.2020.109628 WOS Scopus РИНЦ

Published print:

Nov 1, 2020

Web of science	WOS:000581700400001
Scopus	2-s2.0-85090852318
Elibrary	45291484
OpenAlex	W3081767104