Generation of oxodiazonium ions 3. Synthesis of [1,2,5]oxadiazolo[3,4-c]cinnoline-1,5-dioxides

Generation of oxodiazonium ions 3. Synthesis of [1,2,5]oxadiazolo[3,4-c]cinnoline-1,5-dioxides Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2011, Volume: 60, Number: 10, Pages: 2046-2050 Pages count : 5 DOI: 10.1007/s11172-011-0311-8

Authors

Zelenov V.P. ¹ , Voronin A.A. ¹ , Churakov A.M. ¹ , Klenov M.S. ¹ , Strelenko Yu.A. ¹ , Tartakovsky V.A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

A reaction of 4-(N-nitramino)-3-phenylfuroxane with the Ac2O/H2SO4 system leads to the formation of [1,2,5]oxadiazolo[3,4-c]cinnoline-1,5-dioxide, the first representative of furoxanocinnolines. The reaction presumably proceeds through the transformation of the nitramine fragment NHNO2 to the oxodiazonium ion [N=N=O]+ with subsequent intramolecular attack by this cation on the phenyl ring. Furoxanocinnoline is also formed in the reaction of the 4-(N-nitramino)-3-phenylfuroxane O-methyl derivative with H2SO4. It is assumed that this reaction also proceeds with involvement of the intermediate cation [N=N=O]+ formed by the protonation of the N=N(O)OMe group and subsequent elimination of MeOH. 7-Nitro derivative is formed when furoxanocinnoline is nitrated with the concentrated HNO3/H2SO4 mixture. The compounds obtained were characterized by 1H, 13C, and 14N NMR spectroscopy.

Zelenov V.P. , Voronin A.A. , Churakov A.M. , Klenov M.S. , Strelenko Y.A. , Tartakovsky V.A.
Generation of oxodiazonium ions 3. Synthesis of [1,2,5]oxadiazolo[3,4-c]cinnoline-1,5-dioxides
Russian Chemical Bulletin. 2011. V.60. N10. P.2046-2050. DOI: 10.1007/s11172-011-0311-8 WOS Scopus OpenAlex

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