Highly efficient synthesis of polyfluorinated 2-mercaptobenzothiazole derivatives Full article
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Journal of Fluorine Chemistry
ISSN: 0022-1139 |
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| 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 | ||||||
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Abstract:
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.
Cite:
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 OpenAlex
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 OpenAlex
Dates:
| Published print: | Aug 1, 2018 |
Identifiers:
| Web of science: | WOS:000439402500012 |
| Scopus: | 2-s2.0-85048531774 |
| Elibrary: | 35782620 |
| OpenAlex: | W2808312035 |