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Synthesis of hetarylsulfanyl- and hetaryloxyfuroxans by nucleophilic substitution of nitro group in nitrofuroxans with heterocyclic thiol and hydroxy derivatives*

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Chemistry of Heterocyclic Compounds Aims and scope

We report a general method for the synthesis of previously unknown heterocyclic systems containing furoxan and heterocyclic fragments linked by S- and О-bridges, based on nucleophilic substitution of nitro group in 4-nitrofuroxans with HetS and HetO groups introduced by reactions with hetarylthiols and hydroxy heterocycles in 1,8-diazabicyclo[5.4.0]undec-7-ene/МеCN system at room temperature. We showed that hetarylthiols reacted with 4-nitrofuroxans containing aliphatic, benzyl, and aromatic substituents at the ring С-3 atom, allowing to obtain a library of previously unknown hetarylsulfanylfuroxans, while the reaction with hydroxy heterocycles was successful only in the case of 4-nitro-3-phenylfuroxan, the rest of the nitrofuroxans showing low reactivity, and substitution products could be obtained only in certain cases. 4-Nitrofuroxans with electron-withdrawing substituents (NO2, CONH2) acted as oxidants, forming 1,2-di(hetaryl)disulfides.

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The work was performed with financial support from the Russian Science Foundation (grant 14-50-00126).

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Authors and Affiliations

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

    Leonid L. Fershtat, Margarita A. Epishina, Alexander S. Kulikov, Marina I. Struchkova & Nina N. Makhova

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  1. Leonid L. Fershtat
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  2. Margarita A. Epishina
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  3. Alexander S. Kulikov
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  4. Marina I. Struchkova
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  5. Nina N. Makhova
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Correspondence to Nina N. Makhova.

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*A brief report is available.1

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(2), 176–186

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Fershtat, L.L., Epishina, M.A., Kulikov, A.S. et al. Synthesis of hetarylsulfanyl- and hetaryloxyfuroxans by nucleophilic substitution of nitro group in nitrofuroxans with heterocyclic thiol and hydroxy derivatives*. Chem Heterocycl Comp 51, 176–186 (2015). https://doi.org/10.1007/s10593-015-1678-5

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  • DOI: https://doi.org/10.1007/s10593-015-1678-5

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