Advances in the chemistry of monocyclic amino- and nitrofuroxans

Published data of the last 20–25 years dealing with the development of methods of synthesis and study of the reactivity of monocyclic amino- and nitrofuroxans are considered. The regularities of the synthesis of aminofuroxans by Schmidt and Curtius rearrangements with participation of acetyl- and azido-carbonylfuroxans, respectively, and features of the transformation of functional substituents in aminofuroxans are discussed. In consideration of the reactivity of aminofuroxans, the attention is focused on the oxidation and diazotization and the Mannich reaction. The methods of synthesis of nitrofuroxans based on oxidation of nitroglyoximes and nitrosation of unsaturated compounds and dipotassium salts of 2-substituted 2-hydroximino-1,1'-dinitroethanes are considered. The reactivity of nitrofuroxans comprises nucleophilic substitution, reduction and thermal furoxan ring opening to give nitrile oxides.
Bibliography — 111 references.