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4,5-Dichloro-1,2-dithiole-3-thione in the synthesis of benzimidazole, benzoxazole and benzothiazole derivatives of 1,3-dithioles

Vladimir Anatol'evich Ogurtsov ¹

Vladimir Anatol'evich Ogurtsov

Oleg Alexeevich Rakitin ¹

Oleg Alexeevich Rakitin

Charles W Rees ²

Charles W Rees

Alexey Aleksandrovich Smolentsev ¹

Alexey Aleksandrovich Smolentsev

¹ N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation

² Department of Chemistry, Imperial College London, London, UK

10.1070/MC2003v013n02ABEH001750

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Published 2003-04-28

Communication , Volume 13, Issue 2, 50-51

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Ogurtsov V. A. et al. 4,5-Dichloro-1,2-dithiole-3-thione in the synthesis of benzimidazole, benzoxazole and benzothiazole derivatives of 1,3-dithioles // Mendeleev Communications. 2003. Vol. 13. No. 2. pp. 50-51.

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Ogurtsov V. A., Rakitin O. A., Rees C. W., Smolentsev A. A. 4,5-Dichloro-1,2-dithiole-3-thione in the synthesis of benzimidazole, benzoxazole and benzothiazole derivatives of 1,3-dithioles // Mendeleev Communications. 2003. Vol. 13. No. 2. pp. 50-51.

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TY - JOUR

DO - 10.1070/MC2003v013n02ABEH001750

UR - https://mendcomm.colab.ws/publications/10.1070/MC2003v013n02ABEH001750

TI - 4,5-Dichloro-1,2-dithiole-3-thione in the synthesis of benzimidazole, benzoxazole and benzothiazole derivatives of 1,3-dithioles

T2 - Mendeleev Communications

AU - Ogurtsov, Vladimir Anatol'evich

AU - Rakitin, Oleg Alexeevich

AU - Rees, Charles W

AU - Smolentsev, Alexey Aleksandrovich

PY - 2003

DA - 2003/04/28

PB - Mendeleev Communications

SP - 50-51

IS - 2

VL - 13

ER -

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@article{2003_Ogurtsov,

author = {Vladimir Anatol'evich Ogurtsov and Oleg Alexeevich Rakitin and Charles W Rees and Alexey Aleksandrovich Smolentsev},

title = {4,5-Dichloro-1,2-dithiole-3-thione in the synthesis of benzimidazole, benzoxazole and benzothiazole derivatives of 1,3-dithioles},

journal = {Mendeleev Communications},

year = {2003},

volume = {13},

publisher = {Mendeleev Communications},

month = {Apr},

url = {https://mendcomm.colab.ws/publications/10.1070/MC2003v013n02ABEH001750},

number = {2},

pages = {50--51},

doi = {10.1070/MC2003v013n02ABEH001750}

}

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Ogurtsov, Vladimir Anatol'evich, et al. “4,5-Dichloro-1,2-dithiole-3-thione in the synthesis of benzimidazole, benzoxazole and benzothiazole derivatives of 1,3-dithioles.” Mendeleev Communications, vol. 13, no. 2, Apr. 2003, pp. 50-51. https://mendcomm.colab.ws/publications/10.1070/MC2003v013n02ABEH001750.

Abstract

4,5-Dichloro-1,2-dithiole-3-thione 2 undergoes a 1,3-dipolar cycloaddition with DMAD to give stable aliphatic thioacyl chloride 3, which is highly reactive towards nucleophiles such as o-substituted amines to give benzimidazole, benzoxazole and benzothiazole derivatives of 1,3-dithioles 9.