81467-15-4Relevant articles and documents
3-(1-Hydroxyalkyl)-1,4,2-dioxazol-5-ones and 3-Hydroxyoxazolidine-2,4-diones from 2-Hydroxycarbohydroxamic Acids and 1,1'-Carbonyldiimidazole
Geffken, Detlef
, p. 211 - 218 (2007/10/02)
The reaction of 2-hydroxycarbohydroxamic acids 6 with 1,1'-carbonyldiimidazole produces 3-(1-hydroxyalkyl)-1,4,2-dioxazol-5-ones 7 and 3-hydroxyoxazolidine-2,4-diones 8.The formation of the heterocycles 7 and 8 depends largely on the substitution at C-2 of 6.Excess of imidazole causes rapid decomposition of 7 into carbonyl compound 9 and isocyanic acid, which yields the adduct 10 with imidazole.Benzylaminolysis of 7a gives 11 whereas the reaction of 7a with 3-chloroaniline produces the ureas 12 and 14 and benzophenone (9a).From the reaction of 7a with imidazole in a mole ratio of 1 : 1 the decomposition products 9a and 10 and 3-hydroxy-5,5-diphenyloxazolidine-2,4-dione (8a) are obtained.