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


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2015-02

AUTHORS

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

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. More... »

PAGES

176-186

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s10593-015-1678-5

DOI

http://dx.doi.org/10.1007/s10593-015-1678-5

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1017420607


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