Synthesis and reactivity of carbohydroximoyl azides: II. 4-substituted 1,2,5-oxadiazole-3-carbohydroximoyl azides and 1-hydroxy-5-(4-R-1,2,5-oxadiazol-3-yl)tetrazoles View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2001-11

AUTHORS

I. V. Tselinskii, S. F. Mel’nikova, T. V. Romanova

ABSTRACT

Diazotization of 4-amino-1,2,5-oxadiazole-3-carbohydroximoyl chloride gave 4-[chloro(hydroxyimino) methyl]-1,2,5-oxadiazole-3-diazonium salt. Treatment of the latter with NaN3 afforded 4-azido-1,2,5-oxadiazole-3-carbohydroximoyl chloride, and the reaction with NaNO2 yielded 2-cyano-2-hydroxyiminoacetohydroximoyl chloride. By oxidation of 4-amino-1,2,5-oxadiazole-3-carbohydroximoyl azide with KMnO4 in hydrochloric acid 4,4′-dicyano-3,3′-azobis(1,2,5-oxadiazole) was obtained. Azidation of 1,2,5-oxadiazole-3-hydroximoyl chlorides resulted in formation of the corresponding 1,2,5-oxadiazole-3-carbohydroximoylazides which were brought into reactions with acetic anhydride and acetyl chloride. Decomposition of 4-azido-1,2,5-oxadiazole-3-carbohydroximoyl azide gave 4-azido-1,2,5-oxadiazole-3-carbonitrile; treatment of the same compound with gaseous hydrogen chloride in ether afforded 1-hydroxy-5-(4-azido-1,2,5-oxadiazole-3-yl)tetrazole which was converted into the corresponding acetate by reaction with acetic anhydride. More... »

PAGES

1638-1642

Identifiers

URI

http://scigraph.springernature.com/pub.10.1023/a:1013880808801

DOI

http://dx.doi.org/10.1023/a:1013880808801

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1085177909


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