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Nitro derivatives of 2,1,3-benzothiadiazole 1-oxides: synthesis, structural study, and NO release

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Abstract

A convenient one-pot synthesis of nitro derivatives of 2,1,3-benzothiadiazole 1-oxides by the reaction of o-nitroanilines with sulfur monochloride was developed. The structural features of 4-nitrobenzothiadiazole and its N-oxide were considered. High in vitro release of nitric oxide (69%) was found for a 6-nitro-2,1,3-benzothiadiazole sample by the Griess assay, which indicated good prospects for this class of compounds.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    L. S. Konstantinova, E. A. Knyazeva, S. G. Zlotin & O. A. Rakitin

  2. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 9 prosp. Akad. Lavrent’eva, 630090, Novosibirsk, Russian Federation

    Yu. V. Gatilov

Authors
  1. L. S. Konstantinova
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  2. E. A. Knyazeva
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  3. Yu. V. Gatilov
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  4. S. G. Zlotin
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  5. O. A. Rakitin
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Correspondence to O. A. Rakitin.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0095—0101, January, 2018.

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Konstantinova, L.S., Knyazeva, E.A., Gatilov, Y.V. et al. Nitro derivatives of 2,1,3-benzothiadiazole 1-oxides: synthesis, structural study, and NO release. Russ Chem Bull 67, 95–101 (2018). https://doi.org/10.1007/s11172-018-2042-6

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  • DOI: https://doi.org/10.1007/s11172-018-2042-6

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