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Synthesis of stable adducts of highly electrophilic nitro(het)arenes with С-nucleophiles

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Abstract

The reaction of highly electrophilic azolo[b]pyridines with pyrrole and indole derivatives as nucleophiles afforded 1,4-addition products to the pyridine ring. The reactions of structurally similar meta-dinitrobenzo-fused heterocycles (furoxan, thiadiazole, selenadiazole, pyridine) with C-nucleophiles (salts of ketones and 2-nitropropane) gave stable anionic σ-complexes in high yields. Their oxidation led to rearomatization with the formation of the corresponding products of substitution of a hydrogen atom with the nucleophile. The oxidation was generally accompanied by the decomposition of σ-complexes into the parent 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

    A. M. Starosotnikov, M. A. Bastrakov & V. A. Kokorekin

Authors
  1. A. M. Starosotnikov
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  2. M. A. Bastrakov
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  3. V. A. Kokorekin
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Correspondence to A. M. Starosotnikov.

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The authors declare no competing interests.

Additional information

This work was financially supported by the Russian Science Foundation (Project No. 19-73-20259).

No human or animal subjects were used in this research.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 474–478, March, 2022.

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Starosotnikov, A.M., Bastrakov, M.A. & Kokorekin, V.A. Synthesis of stable adducts of highly electrophilic nitro(het)arenes with С-nucleophiles. Russ Chem Bull 71, 474–478 (2022). https://doi.org/10.1007/s11172-022-3435-0

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  • DOI: https://doi.org/10.1007/s11172-022-3435-0

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