Реферат: Methods for the synthesis of [1,2,5]oxadiazolo[3,4-c]cinnoline 5-oxides, which include the reaction of 3-nitramino-4-(R-phenyl)furazans or their O-methyl derivatives with electrophilic agents, have been developed. Unsubstituted [1,2,5]oxadiazolo[3,4-c]cinnoline 5-oxide was synthesized from 3-nitramino-4-phenylfurazan upon the action of phosphorus anhydride or oleum, as well as from O-methyl derivative of 3-nitramino-4-phenylfurazan upon the action of H2SO4, MeSO3H, CF3CO2H and BF3·Et2O, while 6-, 7-, 8-, and 9-nitro-substituted [1,2,5]oxadiazolo[3,4-c]cinnoline 5-oxides — from the corresponding 3-nitramino-4-(nitrophenyl)furazans upon the action of the H2SO4-HNO3 nitrating mixture. A suggestion has been made that an oxodiazonium ion is formed in these reactions from nitramines or their O-methyl derivatives upon the action of electrophilic agents, which is further involved into the intra-molecular reaction of electrophilic aromatic substitution (S EAr) with the aryl group. The structure of [1,2,5]oxadiazolo[3,4-c]cinnoline 5-N-oxides was confirmed by 1H, 13C, and 14N NMR spectra. Theoretical studies by the B3LYP/6-311G(d,p) method of combined molecular system (O-methylated 3-nitramino-4-phenylfurazan + [H3SO4]+) resulted in calculation of thermodynamic parameters of the sequence of cascade elementary reactions leading to the formation of [1,2,5]oxadiazolo[3,4-c]cinnoline 5-oxide.

Библиографическая ссылка: Klenov M.S. , Ratnikov M.O. , Churakov A.M. , Solkan V.N. , Strelenko Y.A. , Tartakovsky V.A.
Generation of oxodiazonium ions 1. Synthesis of [1,2,5]oxadiazolo[3,4-c]cinnoline 5-oxides
Russian Chemical Bulletin. 2011. V.60. N3. P.536-547. DOI: 10.1007/s11172-011-0084-0 WOS Scopus OpenAlex

Идентификаторы БД:

≡ Web of science:	WOS:000294715900023
≡ Scopus:	2-s2.0-80052783524
≡ OpenAlex:	W4230631262

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