Journal
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
Volume 51, Issue 2, Pages 176-186Publisher
SPRINGER
DOI: 10.1007/s10593-015-1678-5
Keywords
hetaryloxyfuroxans; hetarylthiols; hydroxyheterocycles; 4-nitrofuroxans; disulfide bridges; hetarylsulfanylfuroxan library; nucleophilic substitution
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Funding
- Russian Science Foundation [14-50-00126]
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We report a general method for the synthesis of previously unknown heterocyclic systems containing furoxan and heterocyclic fragments linked by S- and D-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/DeD mu CN system at room temperature. We showed that hetarylthiols reacted with 4-nitrofuroxans containing aliphatic, benzyl, and aromatic substituents at the ring D-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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