Advances in the chemistry of monocyclic amino- and nitrofuroxans

The review summarizes data on the development of methods of synthesis and reactivity of monocyclic amino- and nitrofuroxans published in the last 20–25 years. The details of the synthesis of aminofuroxans based on the Schmidt and Curtius rearrangements involving acetyl- and azidocarbonylfuroxans, respectively, are discussed. Specific features of the transformations of functional substituents in aminofuroxans are described. In consideration of the reactivity of aminofuroxans, the attention is focused on the oxidation, diazotization and the Mannich reaction. Methods of synthesis of nitrofuroxans based on the oxidation of nitroglyoximes and the nitrosation of unsaturated compounds and dipotassium salts of 2-substituted 2-hydroxyimino-1,1-dinitroethanes are covered. The reactivity of nitrofuroxans comprises the nucleophilic substitution, reduction and thermal furoxan ring opening to form nitrile oxides. The bibliography includes 111 references.