- Synthesis method of 1, 2, 4-oxadiazole-3, 5-diketone
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The invention relates to a synthesis method of 1, 2, 4-oxadiazole-3, 5-diketone. The method comprises the following steps: placing a reaction mixed solution of a compound 1 and an alkali solution in a reaction system, adding an oxidizing agent, reacting for a period of time, adjusting the pH to be acidic, performing filtering, and recrystallizing a filter cake to obtain a compound 2; and placing the compound 2, an inorganic solvent and an organic solvent in a reaction system, adding nitrite for a reaction, and after the reaction is finished, performing filtering and recrystallization to obtain the target compound 1, 2, 4-oxadiazole-3, 5-diketone. According to the method, the raw materials are few in variety and easy to obtain; reaction conditions are mild; compared with a synthesis method in the literature 2, the provided method has less three-waste emission and fewer steps; and hydroxylamine is used in the literature 2, and the requirement for equipment in industrial production is strict, while the hydroxylamine does not need to be used in the method, the process is simple, and the requirement for the equipment is low.
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Paragraph 0035-0037; 0040-0041; 0044-0045; 0048
(2021/08/19)
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- A convenient synthesis of 1,2,4-oxadiazolidine-3,5-dione
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A convenient three-step synthesis of 1,2,4-oxodiazolidine-3,5-dione involving debenzylation of 3-benzyloxy-1,2,4-oxadiazol-5(4H)-one with boron tribromide is reported. By contrast with the two known procedures, this synthesis requires only nonhazardous an
- Renaut,Thomas,Bellamy
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p. 265 - 266
(2007/10/02)
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- Synthesis and Biological Activity of Certain Derivatives of Oxazinomycin and Related Oxadiazole Nucleosides
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Oxazinomycin was converted into 2',3',5'-tri-O-acetyloxazinomycin (2) and 2',3'-O-isopropyllideneoxazinomycin (3), respectively.Compound 3 was iodinated and reduced to provide 5'-deoxy-2',3'-O-isopropylideneoxazinomycin (5) which, after acid hydrolysis, provided 5'-deoxyoxazinomycin (6).Alternatively, the iodination of oxazinomycin followed by catalytic hydrogenation also provided 6.Oxazinomycin was treated with 2-acetoxybenzoyl chloride to provide 3'-O-acetyl-2'-chloro-2'-deoxyoxazinomycin (8) which, after reduction with tributyltin hydride, provided 3'-O-acetyl-2'-deoxyoxazinomycin (9).Oxazinomycin was also converted into oxazinomycin 5'-phosphate (10) and into O4,2'-anhydrooxazinomycin (11). 1,2,4-Oxadiazole-3,5-dione (12) was glycosylated to provide 2-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1,2,4-oxadiazole-3,5-dione (13) which, after deacetylation, provided 2-β-D-ribofuranosyl-1,2,4-oxadiazole-3,5-dione (14).Similarly, 12 provided 2-(2-deoxy-β-D-erythro-pentofuranosyl)-1,2,4-oxadiazole-3,5-dione (17); 14 was also converted into the corresponding 2',3'-O-isopropylidene derivative 15.Compound 14 showed significant antiviral activity against herpes simplex virus type 1, in vitro.
- Srivastava, Prem C.,Robins, Roland K.
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p. 1172 - 1177
(2007/10/02)
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