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Synthesis and nucleophilic dearomatization of highly electrophilic [1,2,5]selenadiazolo[3,4-b]pyridines

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Abstract

A number of [1,2,5]selenadiazolo[3,4-b]pyridines were synthesized on the basis of readily available 5-R-2,3-diaminopyridines. It was found that these compounds can be involved into the reactions with C-nucleophiles (1,3-dicarbonyl compounds, indoles) under mild conditions, in some cases with no base required. As a result, stable products of nucleophilic addition to the pyridine ring, 1,4-dihydropyridines fused with selenadiazole ring, were formed in up to 94% yield.

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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

    V. V. Ivanova, A. K. Fedorenko, A. M. Starosotnikov & M. A. Bastrakov

Authors
  1. V. V. Ivanova
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  2. A. K. Fedorenko
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  3. A. M. Starosotnikov
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  4. M. A. Bastrakov
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Corresponding author

Correspondence to M. A. Bastrakov.

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Dedicated to the Academician of the Russian Academy of Sciences V. A. Tartakovsky on the occasion of his 90th birthday.

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1826–1829, August, 2022.

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Ivanova, V.V., Fedorenko, A.K., Starosotnikov, A.M. et al. Synthesis and nucleophilic dearomatization of highly electrophilic [1,2,5]selenadiazolo[3,4-b]pyridines. Russ Chem Bull 71, 1826–1829 (2022). https://doi.org/10.1007/s11172-022-3596-x

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  • DOI: https://doi.org/10.1007/s11172-022-3596-x

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