Generation of oxodiazonium ions 2. Synthesis of benzotetrazine-1,3-dioxides from 2-(tert-butyl-NNO-azoxy)-N-nitroanilines

Generation of oxodiazonium ions 2. Synthesis of benzotetrazine-1,3-dioxides from 2-(tert-butyl-NNO-azoxy)-N-nitroanilines Full article

Journal

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

Output data

Year: 2011, Volume: 60, Number: 10, Pages: 2040-2045 Pages count : 6 DOI: 10.1007/s11172-011-0310-9

Authors

Klenov M.S. ¹ , Zelenov V.P. ¹ , Churakov A.M. 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 new method for the synthesis of benzotetrazine-1,3-dioxides was developed, which involves the reaction of 2-(tert-butyl-NNO-azoxy)-N-nitroanilines with the Ac2O/H2SO4 system. This method was also used for the synthesis of [1,2,5]oxadiazolo[3,4-c]cinnoline-5-oxide from 3-nitramino-4-phenylfurazan. The suggested mechanism of these reactions involves the formation of the intermediate oxodiazonium ion, resulting from acetylation of the oxygen atom of the nitramine group, followed by protonation and ionic dissociation. Then the oxodiazonium ion enters the intramolecular reaction with the neighboring tert-butyl-NNO-azoxy or phenyl group to form the corresponding heterocyclic systems.

Klenov M.S. , Zelenov V.P. , Churakov A.M. , Strelenko Y.A. , Tartakovsky V.A.
Generation of oxodiazonium ions 2. Synthesis of benzotetrazine-1,3-dioxides from 2-(tert-butyl-NNO-azoxy)-N-nitroanilines
Russian Chemical Bulletin. 2011. V.60. N10. P.2040-2045. DOI: 10.1007/s11172-011-0310-9 WOS Scopus OpenAlex

≡ Web of science:	WOS:000305679700013
≡ Scopus:	2-s2.0-84864553190
≡ OpenAlex:	W1998771703