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

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