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1.
Oxidation of one of the amino groups of 2-bromo-4,6-dichloro-1,3-phenylenediamine to the nitroso group followed by its conversion into thetert-butyl-NNO-azoxy group afforded a derivative ofm-(tert-butyl-NNO-azoxy)aniline,viz., 2-bromo-3-(tert-butyl-NNO-azoxyl)-4,6-dichloroaniline. Analogously, the second amino group was converted into thetert-butyl-NNO-azoxy group to form a derivative of 1,3-bis(tert-butyl-NNO-azoxy)benzene,viz., 3-bromo-2,4-bis(tert-butyl-NNO-azoxyl)-1,5-dichlorobenzene The reaction of the latter with ammonia yielded 2-amino- and 2,4-diamino-substituted 1,3-bis-(tert-butyl-NNO-azoxyl)benzenes. For Part 1, see Ref. 1. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2126–2130, November, 1999.  相似文献   

2.
Oxidation of 4,6-dichloro-1,3-phenylenediamine with Caro's acid yields the corresponding dinitrosobenzene, which reacts withN,N-dibromo-tert-butylamine to give 1,5-bis(tert-butyl-NNO-azoxy)-2,4-dichlorobenzene. Treatment of the latter with ammonia yields 4-amino-and 4,6-diamino-1,3-bis(tert-butyl-NNO-azoxy)benzenes. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya. No. 7, pp. 1307–1310, July, 1999.  相似文献   

3.
Treatment of 2-(tert-butyl-NNO-azoxy)anilines with phosgene at 20 °C was proposed as a novel route to 1,2,4-benzotriazin-3(4H )-one 1-oxides. This method involves a new reaction, viz., an intramolecular interaction of the tert-butyl-NNO-azoxy group with a C-electrophile (leading to the formation of the N(2)—C(3) bond of the triazine ring) followed by elimination of the tert-butyl group. Complete assignment of the signals in the 1H and 13C NMR spectra of the compounds obtained was performed. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1507–1509, August, 2007.  相似文献   

4.

5-Amino-(tert-butyl-NNO-azoxy)-1,2,3,4-tetrazine 1,3-dioxide reacts with nitronium tetra-fluoroborate to give 5-amino-6-nitro-1,2,3,4-tetrazine 1,3-dioxide. This compound is of interest as a new energetic material. A plausible reaction mechanism involves electrophilic substitution of the tert-butyl-NNO-azoxy group by the nitro group.

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5.
New approach to the synthesis of benzo[e][1,2,3,4]tetrazine 1,3-dioxides   总被引:2,自引:0,他引:2  
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.  相似文献   

6.
A new approach to the synthesis of 4-amino-5-(tert-butyl-NNO-azoxy)-2-R-2H-1,2,3-triazole 1-oxides 1 was developed. Compounds 1 were obtained by reactions of 3-amino-4-(tert-butyl-NNO-azoxy)furoxan with aliphatic amines RNH2 (R = Me, Et, Pri, Bu, and But). 4-Amino-5-(tert-butyl-NNO-azoxy)-2-tert-butyl-2H-1,2,3-triazole 1-oxide was transformed under the action of acids into 4-amino-5-(tert-butyl-NNO-azoxy)-1-hydroxy-1H-1,2,3-triazole. Methylation of the latter with diazomethane mainly involves the O atom of the triazole oxide ring. Reduction of compounds 1 gave 4-amino-5-(tert-butyl-NNO-azoxy)-2-R-2H-1,2,3-triazoles and 4-amino-5-(tert-butyldiazenyl)-2-R-2H-1,2,3-triazoles (R = Me, Pri, and But). The structures of the compounds obtained were confirmed by 1H, 13C, and 14N NMR spectroscopy.  相似文献   

7.
1,2,3,4-Tetrazino[5,6-g]benzo-1,2,3,4-tetrazine 1,3,7,9-tetraoxides, which possess an-thracene-type annulation of the benzene ring with two 1,2,3,4-tetrazine 1,3-dioxide fragments, were obtained for the first time from aminobenzenes containing tert-butyl-NNO-azoxy groups in appropriate positions. Complete assignments of the signals in the 1H, 13C, and 14N NMR spectra of the compounds obtained were carried out. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1595–1599, September, 2006.  相似文献   

8.
2-(tert-Butyl-NNO-azoxy)aniline was prepared by selective reduction of 2-(tert-butyl-NNO-azoxy)nitrobenzene. Its bromination yielded the correspondingpara-bromo- andortho, para-dibromoanilines (3a,b).meta-Bromoanilines (6a,b) were synthesized by selective replacement of theortho-bromine atoms in ortho,para-bromo(tert-butylazoxy)benzenes (5a,b) by ammonia in toluene under pressure.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1620–1623, September, 1994.This work was carried out with the financial support of the Russian Foundation for Basic Research (Project No. 93-03-18461).  相似文献   

9.
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.  相似文献   

10.
3-Amino-4-(tert-butyl-NNO-azoxy)furoxan (1a) and 4-amino-3-(tert-butyl-NNO-azoxy)-furoxan (1b) and their acetyl derivatives 6a,b were obtained. The equilibria 1a ai 1b and 6a ? 6b were studied. Furoxan 6b can undergo thermal rearrangement into 3-[(tert-butyl-NNO-azoxy)(nitro)methyl]-5-methyl-1,2,4-oxadiazole (7), prolonged heating of which gives N-(2-tert-butyl-5-nitro-1-oxido-2H-1,2,3-triazol-4-yl)acetamide (8). With the transformation 78 as an example, the possibility of participation of the azoxy group in the Boulton-Katritzky rearrangements was demonstrated for the first time.  相似文献   

11.
A reaction of 2,2-bis(methoxy-NNO-azoxy)ethyl methanesulfonate with ethyl(diisopropyl)amine afforded 1,1-bis(methoxy-NNO-azoxy)ethene (3). Compound 3 was examined by X-ray diffraction analysis. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 619–624, March, 2008.  相似文献   

12.
The first representative of the alkoxy-NNO-azoxy olefin series, viz., methoxy-NNO-azoxyethene, was synthesized by the pyrolysis of 1,1-bis(methoxy-NNO-azoxy)ethane.  相似文献   

13.
A new method for the synthesis of benzotetrazine-1,3-dioxides was developed from the 2-(tert-butyl-NNO-azoxy)-N-nitroaniline O-alkyl derivatives upon the action of strong acids (H2SO4, MeSO3H, CF3CO2H) or BF3·Et2O. A mechanism suggested for these reactions includes transformation of the N=N(O)OR group (R = Me, Pri) to the oxodiazonium ion (N=N=O)+, which intramolecularly reacts with the neighboring tert-butyl-NNO-azoxy group, furnishing the tetrazine-1,3-dioxide ring.  相似文献   

14.
A convenient procedure for the synthesis of N-nitroaminofurazans by nitration of primary 3-amino-4-R-furazans (R = Me, NO2, phenyl-, methyl-NNO-azoxy-, tert-butyl-NNO-azoxy-, tert-butyldiazenyl-, etc.) with 66–77% aqueous nitric acid was developed. Depending on the concentration of HNO3, the reaction is carried out at a temperature from 18 to 55 °C, the yield of the products is 80–99%. 3-Nitramino-4-phenylfurazan with unsubstituted benzene ring was obtained by nitration of 3-amino-4-phenylfurazan.  相似文献   

15.
Reactions of 3(4)-amino-4(3)-(tert-butyl-NNO-azoxy)furoxans with excess (NO2)2S2O7 or with a HNO3—H2SO4—Ac2O mixture unexpectedly produce [1,2,5]oxadiazolo[3,4-e]?[1,2,3,4]tetrazine 4,6-di-N-oxide (furazanotetrazine dioxide) and products of amino group oxidation (mainly to the corresponding azofuroxans) instead of the expected furoxanotetrazine dioxides. In some cases, individual (Z)-3,3´-((E)-diazene-1,2-diyl)-bis-((Z)-2-tert-butyl-1-oxidodiazenyl)-1,2,5-oxadiazole 2-oxide) was isolated. Formation of furazanotetrazine dioxides was observed in the reaction of 3-nitramino-4-(tert-butyl-NNO-azoxy)furoxan sodium salt with H2SO4 in Ac2O. Quantum chemical calculation at the DFT/B3LYP/6-31G(d) level of theory was used to estimate several aspects of the reactivity of 3(4)-nitramino-4(3)-(tert-butyl-NNO-azoxy)furoxans in a comparison with 3(4)-nitramino-4(3)-phenylfuroxans and the possible causes of the observed transformations were revealed.  相似文献   

16.
A reaction of 1,1-bis(methoxy-NNO-azoxy)ethene with nitroform at ∼20 °C gave 1,1-bis-(methoxy-NNO-azoxy)-3,3,3-trinitropropane.  相似文献   

17.
A series of di(NON-azoxy)formals and some relatedN-alkyl-N′-alkoxydiazeneN-oxides were prepared by the reaction ofN-nitrosohydroxylamine salts with dihaloalkanes. The dependence of the yield of di(methyl-NON-azoxy)formal on the reaction conditions and the nature of the cation was studied. The structure of di(methyl-NON-azoxy)formal and di(phenyl-NON-azoxy) formal as well as of the coppertert-butylnitrosohydroxylaminate was established by X-ray diffraction analysis. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1486–1493, August, 1997.  相似文献   

18.
New methods were developed for the synthesis of [1,2,5]oxadiazolo[3,4-e][1,2,3,4]tetrazine 4,6-dioxide from 4-(tert-butyl-NNO-azoxy)-N-nitro-1,2,5-oxadiazol-3-amine or its alkali metal salts and acid anhydrides (or chlorides) in the presence of strong acids. The yield of [1,2,5]oxadiazolo[3,4-e][1,2,3,4]tetrazine 4,6-dioxide in acetic anhydride in the presence of sulfuric acid or sulfuric anhydride at 20°C in 20 min attained 83%. A general mechanism was proposed for the reactions under study. Acetyl group behaved for the first time as departing group in the synthesis 1,2,3,4-tetrazine 1,3-dioxides, and [1,2,5]oxadiazolo[3,4-e][1,2,3,4]tetrazine 4,6-dioxide was obtained in 47% yield from N-[4-(acetyl-NNO-azoxy)-1,2,5-oxadiazol-3-yl]acetamide.  相似文献   

19.
(E)-2-[2,2-Bis(tert-butyl-NNO-azoxy)-1-(methylsulfinyl)vinyl]-1-isopropoxydiazene 1-oxide reacts with boron trifluoride etherate (BF3?Et2O) producing 2-tert-butyl-N-nitro-2H-tetrazolo-5-carboxamide 4-oxide and 2-tert-butyl-2H-tetrazolo-5-carbonitrile 4-oxide but not the expected 1,2,3,4-tetrazine 1,3-dioxide derivative. This reaction direction can be explained by cationic domino cyclization, the key stage of which is coupling of the oxodiazonium ion with the geminal MeS(O) group. Structure of N-nitrocarboxamide was confirmed by X-ray diffraction analysis.  相似文献   

20.
2,2-Bis(alkoxy-NNO-azoxy)propane-1,3-diols reacted with thionyl chloride to give previously unknown 5,5-bis(methoxy-NNO-azoxy)- and 5,5-bis(ethoxy-NNO-azoxy)-1,3,2-dioxathiane 2-oxides. Replacement of the hydroxy groups by chlorine is a minor reaction path. According to the X-ray diffraction data, the heteroring in the molecule of 5,5-bis(methoxy-NNO-azoxy)-1,3,2-dioxathiane 2-oxide adopts a chair conformation with axial orientation of the S=O bond.  相似文献   

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