Highly efficient synthesis of polyfluorinated 2-mercaptobenzothiazole derivatives

Highly efficient synthesis of polyfluorinated 2-mercaptobenzothiazole derivatives Full article

Journal

Journal of Fluorine Chemistry
ISSN: 0022-1139

Output data

Year: 2018, Volume: 212, Pages: 130-136 Pages count : 7 DOI: 10.1016/j.jfluchem.2018.06.001

Tags

Polyfluorinated anilines; Polyfluorinated heterocycles; Tandem reaction; Reaction mechanism; 2-Mercaptobenzothiazoles

Authors

Politanskaya Larisa ^1,2 , Duan Zequn ² , Bagryanskaya Irina ^1,2 , Eltsov Ilia ² , Tretyakov Evgeny ^1,2 , Xi Chanjuan ³

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, Ac Lavrentiev Ave 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Pirogova St 2, Novosibirsk 630090, Russia
3	(Данные Web of science) Tsinghua Univ, Dept Chem, Minist Educ, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Beijing 100084, Peoples R China

A convenient and efficient method for the synthesis of polyfluorinated 2-mercaptobenzothiazoles from the corresponding aniline derivatives and CS2, mediated by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in toluene is described. The reaction proceeded via nucleophilic attack at the carbon atom of carbon disulfide by the nitrogen atom of NH2-group in arene followed by selective intramolecular fluorine atom substitution in the ortho-position to the amino group. This synthetic methodology could be used to prepare fluorinated 2-mercaptobenzothiazole containing alkynyl group in good to excellent yields. The reaction takes place under very mild reaction conditions (50 degrees C) and uses readily available starting materials.

Politanskaya L. , Duan Z. , Bagryanskaya I. , Eltsov I. , Tretyakov E. , Xi C.
Highly efficient synthesis of polyfluorinated 2-mercaptobenzothiazole derivatives
Journal of Fluorine Chemistry. 2018. V.212. P.130-136. DOI: 10.1016/j.jfluchem.2018.06.001 WOS Scopus РИНЦ

Published print:

Aug 1, 2018

Web of science	WOS:000439402500012
Scopus	2-s2.0-85048531774
Elibrary	35782620
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