98778-06-4

Usage

Uses

Used in Medicinal Chemistry:
[1,2,5]Oxadiazolo[3,4-b]pyrazine,1,3,5,6-tetrahydro-(9CI) is used as a building block for the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Material Science:
In the field of material science, [1,2,5]Oxadiazolo[3,4-b]pyrazine,1,3,5,6-tetrahydro-(9CI) is used as a component in the development of novel materials with specific properties. Its incorporation into different material systems can lead to advancements in areas such as electronics, optics, and nanotechnology.

Upstream product

• 4331-99-1 2,3-bis(hydroxyimino)piperazine 
• 25883-65-2 [1,2,5]oxadiazolo[3,4-b]pyrazine 

Downstream Products

• 98778-15-5 1,4-dinitrofurazano<3,4-b>piperazine 

Relevant academic research and scientific papers

A Re-examination of the reaction of 3,4-diamino[1,2,5]oxadiazole with glyoxal

Reaction coordinate mapping was used to study the reaction of 3,4-diamino[1,2,5]oxadiazole (3,4-diaminofurazan) and 3,4-diamino[1,2,5] thiadiazole with glyoxal. The thiadiazole was known to give a good yield of [1,2,5]thiadiazolo[3,4-b]pyrazine, whereas the oxadiazole had not yielded, until now, [1,2,5]oxadiazolo[3,4-b]pyrazine (or furazano[2,3-b]pyrazine). The calculations suggested that the diols, 5,6-dihydroxy-4,5,6,7-tetrahydro[1,2,5] oxadiazolo[3,4-b]pyrazine and 5,6-dihydroxy-4,5,6,7-tetrahydro[1,2,5] thiadiazolo[3,4-b]pyrazine should be stable intermediates, and once formed, should provide a pathway to the target compounds via two dehydration steps, under forcing conditions. With this information in mind, the reactions of 3,4-diamino[1,2,5]oxadiazole with glyoxal and pyruvic aldehyde were re-examined. The reaction of 3,4-diamino[1,2,5]oxadiazole with glyoxal and pyruvic aldehyde produced, under slightly basic conditions, a near quantitative yield of the expected initial products, 5,6-dihydroxy-4,5,6,7-tetrahydro[1,2,5]oxadiazolo[3, 4-b]pyrazine and the 5-methyl analog, respectively. The diols were easily isolated by lyophilizing the aqueous reaction mixture. The diols were pyrolized on silica gel at 160°C to give the desired [1,2,5]oxadiazolo[3,4-b]pyrazine and the 5-methyl analog. Both compounds were easily reduced to the corresponding 4,5,6,7-tetrahydro-derivative using sodium borohydride in THF/methanol. The [1,2,5]oxadiazolo[3,4-b]pyrazine also displayed other interesting chemistry.

Synthesis and Chemistry of Some Furazano- and Furoxanopiperazines

A series of N,N'-disubstituted furazano- and furoxanopiperazines 1a-d and 2b-d have been synthesized from N,N'-disubstituted 2,3-piperazinedione dioximes 5a-d by base-promoted dehydration and by basic potassium ferricyanide oxidation, respectively.The N,N'-disubstituted 2,3-piperazinedione dioximes were synthesized by reacting the appropriate N,N'-disubstituted ethylenediamine with dichloroglyoxime.Also studied was the reaction of 3,4-diaminofurazan with glyoxal and formaldehyde.The compounds have been studied by 1H and 13C NMR spectroscopy.