Benzo-1,2,3,4-tetrazine 1,3-dioxides annulated with tetraazapentalene systems 3. Annulation at the C(7)—C(8) bond

Thermolysis of 7-azido-8-(2H-1,2,3-triazol-2-y1)-1,2,3,4-benzotetrazine 1,3-dioxide and 7-azido-8-(l H-1,2,3-triazol-l-yl)-1,2,3,4-benzotetrazine 1,3-dioxide afford new heterocyclic systems, viz., 7,11-dehydro-7H, 11H [1,2,3]triazolo[l′,2′:2,3][1,2,3]triazolo[4,5-f]-[1,2,3,4]benzotetrazine 1,3-dioxide and 7,9-dehydro-7 H, 9H [1,2,3]triazolo[2′,1′:2,3]-[1,2,3]triazolo[4,5-f][1,2,3,4]benzotetrazine 1,3-dioxide, respectively, and their thermal stability has been studied.     

New approach to the synthesis of benzo[e][1,2,3,4]tetrazine 1,3-dioxides

A new approach to the synthesis of benzo[e][1,2,3,4]tetrazine 1,3-dioxides involves the treatment ofN-nitroanilines containing anortho-(tert-butyl-NNO-azoxy) group with phosphoric anhydride or phosphorus pentachloride. The reaction is supposed to proceed through an intermediate diazonium oxide cation. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya. No. 3, pp. 480–484, March, 2000.     

Synthesis of 5-amino-6-(nitro-NNO-azoxy)-1,2,3,4-tetrazine 1,3-dioxide

Russian Chemical Bulletin - A reaction of 5-amino-6-(tert-butyl-NNO-azoxy)-1,2,3,4-tetrazine 1,3-dioxide with nitronium tetrafluoroborate affords 5-amino-6-(nitro-NNO-azoxy)-1,2,3,4-tetrazine...     

Trimethylsilylation and methylation of 1-hydroxybenzotriazole 3-oxide

Trimethylsilylation and methylation of 1 -hydroxybenzotriazole 3-oxide (1) proceed regioselectively and afford 1-trimethylsilyloxy- and 1-methoxybenzotriazole 3-oxides, respectively. The first compound easily undergoes fast hydrolysis and methanolysis, but does not react with nitroethane at 20 °C. A fast reversible 1,5-O,O-migration of the SiMe₃ group is observed for this compound.The authors thank V. I. Gulevskaya for DTA analysis of compound4.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2283–2285, November, 1995.The present work was supported by the Russian Foundation for Basic Research (project No. 93-03-18461).     

Annulated benzotetrazine 1,3-dioxides 2.* [1,2,5]Oxadiazolo[3,4-f ][1,2,3,4]benzotetrazine 1,3,7-trioxide

Thermolysis of 8-azido-7-nitrobenzotetrazine 1,3-dioxide led to benzotetrazine 1,3-dioxide annulated with the furoxan ring at the C(7)—C(8) bond. Complete assignment of the signals in the ¹³C NMR spectrum of the compound obtained was performed. Attempted syntheses of benzotetrazine 1,3-dioxides annulated with a furoxan ring at the C(6)—C(7) bond or two furoxan rings at the C(5)—C(6) and C(7)—C(8) bonds were unsuccessful. Published in russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 341–345, February, 2006.     

New approach for the synthesis of isoxazoline-N-oxides

A strategy for the synthesis of isoxazoline-N-oxides (cyclic five-membered nitronates) from primary nitro compounds and olefins is described. The key step of the process involves 1,3-dipolar cycloaddition of corresponding 1-bromosilyl nitronates with alkenes. [reaction: see text]     

Novel synthesis of α-nitroalkenes from nitroalkanes via halogenation of intermediate N,N-bis(silyloxy)enamines

An approach to conjugated nitroalkenes via oxidation of N,N-bis(silyloxy)enamines with bromine or iodine in the presence of tetra-n-butylammonium acetate is described. The acetate ion plays a key role by acting as a mild desilylating reagent. This new strategy allows the synthesis of α-nitroalkenes from the corresponding nitroalkanes.     

Dinitramide and its salts

The dinitramide anion shows ambident properties. Its reactions with alkylating reagents give rise toN- orO-alkylated products or their mixtures. The reactions of alkylated products with bases were studied.For the previous communication, see V. A. Shlyapochnikov, G. I. Oleneva, N. O. Cherskaya, O. A. Luk'yanov, V. P. Gorelik, O. V. Anikin, and V. A. Tartakovsky,Izv. Akad. Nauk, Ser. Khim., 1994, 1610 [Russ. Chem. Bull., 1994,43, No. 11 (Engl. Transl.)].Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1775–1778, October, 1994.