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Highly efficient synthesis of polyfluorinated 2-mercaptobenzothiazole derivatives. / Politanskaya, Larisa; Duan, Zequn; Bagryanskaya, Irina et al.

In: Journal of Fluorine Chemistry, Vol. 212, 01.08.2018, p. 130-136.

Research output: Contribution to journal › Article › peer-review

Harvard

Politanskaya, L, Duan, Z, Bagryanskaya, I, Eltsov, I, Tretyakov, E & Xi, C 2018, 'Highly efficient synthesis of polyfluorinated 2-mercaptobenzothiazole derivatives', Journal of Fluorine Chemistry, vol. 212, pp. 130-136. https://doi.org/10.1016/j.jfluchem.2018.06.001

APA

Politanskaya, L., Duan, Z., Bagryanskaya, I., Eltsov, I., Tretyakov, E., & Xi, C. (2018). Highly efficient synthesis of polyfluorinated 2-mercaptobenzothiazole derivatives. Journal of Fluorine Chemistry, 212, 130-136. https://doi.org/10.1016/j.jfluchem.2018.06.001

Vancouver

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 Aug 1;212:130-136. doi: 10.1016/j.jfluchem.2018.06.001

Author

Politanskaya, Larisa ; Duan, Zequn ; Bagryanskaya, Irina et al. / Highly efficient synthesis of polyfluorinated 2-mercaptobenzothiazole derivatives. In: Journal of Fluorine Chemistry. 2018 ; Vol. 212. pp. 130-136.

BibTeX

@article{8841fb7d03fe4a3496d2183ced84bdbb,
title = "Highly efficient synthesis of polyfluorinated 2-mercaptobenzothiazole derivatives",
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 °C) and uses readily available starting materials.",
keywords = "2-Mercaptobenzothiazoles, Polyfluorinated anilines, Polyfluorinated heterocycles, Reaction mechanism, Tandem reaction, CRYSTAL-STRUCTURE, CARBON-DISULFIDE, O-HALOANILINES",
author = "Larisa Politanskaya and Zequn Duan and Irina Bagryanskaya and Ilia Eltsov and Evgeny Tretyakov and Chanjuan Xi",
note = "Funding Information: This work has been supported by the Russian Ministry of Science and Education within the 5-100 Excellence Programme. Authors would like to acknowledge the Multi-Access Chemical Service Center SB RAS for spectral and analytical measurements. Publisher Copyright: {\textcopyright} 2018 Elsevier B.V.",
year = "2018",
month = aug,
day = "1",
doi = "10.1016/j.jfluchem.2018.06.001",
language = "English",
volume = "212",
pages = "130--136",
journal = "Journal of Fluorine Chemistry",
issn = "0022-1139",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Highly efficient synthesis of polyfluorinated 2-mercaptobenzothiazole derivatives

AU - Politanskaya, Larisa

AU - Duan, Zequn

AU - Bagryanskaya, Irina

AU - Eltsov, Ilia

AU - Tretyakov, Evgeny

AU - Xi, Chanjuan

N1 - Funding Information: This work has been supported by the Russian Ministry of Science and Education within the 5-100 Excellence Programme. Authors would like to acknowledge the Multi-Access Chemical Service Center SB RAS for spectral and analytical measurements. Publisher Copyright: © 2018 Elsevier B.V.

PY - 2018/8/1

Y1 - 2018/8/1

N2 - 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 °C) and uses readily available starting materials.

AB - 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 °C) and uses readily available starting materials.

KW - 2-Mercaptobenzothiazoles

KW - Polyfluorinated anilines

KW - Polyfluorinated heterocycles

KW - Reaction mechanism

KW - Tandem reaction

KW - CRYSTAL-STRUCTURE

KW - CARBON-DISULFIDE

KW - O-HALOANILINES

UR - http://www.scopus.com/inward/record.url?scp=85048531774&partnerID=8YFLogxK

U2 - 10.1016/j.jfluchem.2018.06.001

DO - 10.1016/j.jfluchem.2018.06.001

M3 - Article

AN - SCOPUS:85048531774

VL - 212

SP - 130

EP - 136

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

SN - 0022-1139

ER -

ID: 14047400