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SYNTHESIS OF HETARYLSULFANYL- AND HETARYLOXYFUROXANS BY NITRO GROUP NUCLEOPHILIC SUBSTITUTION IN NITROFUROXANS UNDER THE ACTION OF HETEROCYCLIC THIOLS AND ALCOHOLS

Леонид Л. Ферштат, Маргарита А. Епишина, Александр С. Куликов, Марина И. Стручкова, Нина Н. Махова
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Abstract


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.

How to Cite
Fershtat, L. L.; Epishina, M. A.; Kulikov, A. S.; Struchkova, M. I.; Makhova, N. N. Chem. Heterocycl. Compd. 2015, 51, 176. [Khim. Geterotsikl. Soedin. 2015, 51, 176.]

For this article in the English edition see DOI 10.1007/s10593-015-1678-5

 


Keywords


hetaryloxyfuroxans; hetarylthiols; hydroxyheterocycles; 4-nitrofuroxans; disulfide bridges; hetarylsulfanylfuroxan library; nucleophilic substitution

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