76440-90-9

Upstream product

• 76440-71-6 2-Hydroxy-N-(tetrahydro-2H-2-pyranyloxy)phenylacetamid 
• 611-71-2 MANDELIC ACID 
• 2292-53-7 (RS)-2-hydroxy-2-phenylacetohydroxamic acid 
• 530-62-1 1,1'-carbonyldiimidazole 
• 76440-80-7 5-Phenyl-3-(tetrahydro-2H-2-pyranyloxy)oxazolidine-2,4-dione 
• 110434-77-0 3-Benzyloxy-4-phenyl-4H-1,5,2-dioxazin-6-on 
• 110434-72-5 4-Phenyl-1,5,2-dioxazinan-3,6-dion 

Downstream Products

• 76440-93-2 5-Phenyl-3-phenylcarbamoyloxyoxazolidine-2,4-dione 

Relevant academic research and scientific papers

Synthesis and Reactivity of 2-Unsubstituted 1,5,2-Dioxazinane-3,6-diones

Treatment of 3-(benzyloxy)-4H-1,5,2-dioxazin-6-ones 5 with trifluoroacetic acid affords 2-unsubstituted 1,5,2-dioxazinane-3,6-diones 4, which undergo rearrangement into 3-hydroxyoxazolidine-2,4-diones 2 under various conditions.Depending on the substitution at C-4, the reaction of 4 with aryl isocyanates produces 2-carbamoyl-1,5,2-dioxazinane-3,6-diones 7 or the oxazolidine derivatives 8.Catalytic hydrogenation of 5b, c gives 2-hydroxy carboxamides 6a, b.

3-(1-Hydroxyalkyl)-1,4,2-dioxazol-5-ones and 3-Hydroxyoxazolidine-2,4-diones from 2-Hydroxycarbohydroxamic Acids and 1,1'-Carbonyldiimidazole

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.

3-Alkoxyoxazolidine-2,4-diones from N-Alkoxy-2-hydroxycarboxamides and 1,1'-Carbonyldiimidazole

Reaction of N-alkoxy-2-hydroxycarboxamides 3 with 1,1'-carbonyldiimidazole produces N-alkoxyoxazolidine-2,4-diones 4.Hydrolysis of N-(tetrahydro-2H-2-pyranyloxy)oxazolidine-2,4-diones affords 3-hydroxyoxazolidine-2,4-diones 5 which are converted by the reaction with phenyl isocyanate into 7 and with benzoyl chloride into 8.Benzylaminolysis of 4 gave 3-benzyloxazolidine-2,4-diones 10.