3,4-bis(4-nitrofurazan-3-yl)-furazan

FIELD: chemistry.

SUBSTANCE: invention relates to nitro-derivatives of polycyclic heterocyclic compounds, more specifically to a heterocyclic compound containing two nitrofurazan rings, directly bonded to a furazan ring, and specifically to 3,4-bis(4-nitrofurazan-3-yl)-furazan .

EFFECT: 3,4-bis(4-nitrofurazan-3-yl)-furazan as an energy-rich compound.

1 dwg, 1 tbl, 3 ex

 

1. The scope of the invention

The invention relates to the field of nitro-derivatives of polycyclic heterocyclic compounds, more specifically to the field of nitro-derivatives of the trimer 1,2,5-oxadiazole (furazan), which is a high-energy compounds.

2. Description of the prior art

1,2,5-Oxadiazole (furutani), and especially their nitro-derivatives, represent a nitrogen-containing heterocyclic compounds having a high enthalpy of formation and high thermal stability due to the aromatic nature of 1,2,5-oxadiazoles (purananooru) cycle, which makes them very attractive compounds in the chemistry of energy-intensive materials.

The main method of obtaining 3-microprosodic of furazan is the oxidation of the amino group of the corresponding 3-amino derivatives of furazan using hydrogen peroxide, ammonium persulfate, persulfate alkali metals in sulfuric acid at low temperature [Novikova T.S., Mel nikova T.M., Kharitonova O.V., Kulagina V.O., Aleksandrova N.S., Sheremetev A.V., Pivina T.S., Khmel'nitskii L.I. and S.S. Novikov, Mendeleev Commun., 1994, 4, 138-140].

3-nitro-derivatives of 1,2,5-oxadiazole (furazan) and 1,2,5-oxadiazol-2-oxide (furoxone) due to the ease of entry into reactions of nucleophilic substitution of the nitro-group are applied to the E. in organic synthesis for the synthesis of derivatives of 1,2,5-oxadiazole [Sheremetev, AV, Mantseva E.V., Aleksandrova N.S., Kuz'min V.S. Khmel'nitskii L.I. - Mendeleev Commun., 1995, 5 (1), 25-27; Sheremetev A.B., Aleksandrova N.S. - Mendeleev Commun., 6, 1998, 238-239; Sheremetev, A.B., Kharitonova O.V., Mel nikova T.M., Novikova T.S., Kuz'min V.S., Khmel'nitskii L.I. - Mendeleev Commun., 1999, 6 (4), 141-143; Sheremetev A.B., Kulagina V.O., Alexandrova N.S., Dmitriev D.E., Strelenko Y.A. - Propellants, Explosives, Pyrotechnics, 1998, 23, 142-149; Sheremetiev A.B., Kulagina B.O., Kraszewski I.A., Melnikova T.M., Alexandrov NS - Izv. Acad. Sciences, vol. chem., 2002, 8, 1411-1417; A.B. Sheremet'ev, V.G. Andrianov, E.V. bachelor's degree, E.V. Shatunova, NS Aleksandrova I. Yudin, CU Dmitriev, V.V. Averkiev, APPLICANT Antipick. - Izv. Acad. Sciences, vol. chem., 2004, 3, s-586].

3. The invention

The closest analogue is proposed in this document 3,4-bis(3-nitrofurazan-4-yl)-furazan (1) is 3,4-bis(3-nitrofurazan-4-yl)-furoxan (NFF, DNFF) (2), proposed as a new fuse BB [Zhao Feng-qi, Chen Pei, Hu Rong-zu, Luo Yang, Zhang Zhi-zhong, Zhou Yan-shui, Yang Xu-wu, Gao Yin, Gao Sheng-li, Shi Qi-zhen. - Journal of Hazardous Materials, A 113, 2004, page 67-71; Wang J., Li J.S., Huamg Y.G., Dong H.S. - Proc. of the 11thseminar: New Trends in Research of Energetic Materials, Czech Republic, Pardubice, April 09-11, 2008, p.182-193], and also considered as a high-energy compound [Zhou Yanshui, Wang Bozhou, Li Jiankang, Zhou Cheng, Hu Lan, Chen Zhiqun Zhang Zhizhong. - Acta Chimica Sinica, 2011, 69 (14), 1673-1680].

Proposed new connection - 3,4-bis(4-nitrofurazan-3-yl)-furazan as fusible explosive. The structure of 3,4-bis(4-nitrofurazan-3-yl)-furazan signal is to be displayed by formula (1), (figure 1). In contrast to the compounds (2) 3,4-bis(4-nitrofurazan-3-yl)-furazan does not contain in its structure ekzoticheskoy N-oxide group, the presence of which caused such a negative connection properties (2), as the volatility of the action of bases, high sensitivity to mechanical impact.

The proposed compound (1) can be obtained by oxidation of the known compounds of 3,4-bis(3-aminopyrazine-4-yl)-furazan (3,4-bis(4-amino-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole)) [PV Anokhina, T. Romanova, SF Melnikova, I. celinskij. - Journal. Org. Chemistry, 2011, 47(10), 1575-1575] or N, N-dialling derived compounds with hydrogen peroxide in sulfuric acid with the addition of such organic solvents, such as acetonitrile, acetic acid under conditions similar to those used in the synthesis of compound (2) [Zhou Yanshui, Wang Bozhou, Li Jiankang, Zhou Cheng, Hu Lan, Chen Zhiqun Zhang Zhizhong. - Acta Chimica Sinica, 2011, 69(14), 1673-1680].

3,4-Bis(4-nitrofurazan-3-yl)-furazan (1) has a temperature of Pavle of 86-87°C, the density of the single crystal 1837 kg·m-3speed of detonation at a density 1837 kg·m-38600 m·s-1sensitivity to impact 48% (10 kg, 25 cm), sensitivity to friction 2900 kg/cm2.

3,4-bis(3-nitrofurazan-4-yl)-furazan (1) has a low sensitivity to mechanical impact compared with 3,4-bis(3-nitrofurazan-4-yl)-what Roxana (2), has a lower melting temperature and energy performance is comparable to the intensively studied at present, 1,3 .3m-trinitroazetidine (TNAZ), potenziruemoe for use as a fusible CENTURIES. (1) unlike TNAZ meletus at elevated temperatures.

The proposed structure of compound (1) is proved by the methods of physico-chemical analysis.

An NMR spectrum is1N connection (1) does not contain the signals of the hydrogen atoms. The NMR spectrum-From13(acetone-d6) there are 3 signals of carbon atoms δ(ppm) 139,5(3,4); 142,5(C-2,5); 160,7(1,6); (in contrast to the NMR spectrum-From13(acetone-d6the nearest analogue, compound (2), including 5 signal 5(ppm) to 103.9(C-3); 137, 6mm(C-4); 139,9(C-2); 143,2(-5); 160,0, 160,2, 160,4 (C-1, C-6). The signals of carbon atoms connected with nitrogroup broadened and have low intensity, due to the quadrupole broadening on nuclei14N [N. N. Makhova. Ovchinnikov IV, Khasanov B.N., Khmelnitsky LI - Izv. Acad. nauk SSSR, ser. chem., 1982, 3, 646-649]. In the mass spectrum of the obtained product has a low-intensity peak of the molecular ion, C6N8O4, [M]=296, 5%; [M-30], 6%, (M-NO); 220, 25%; 190, 23%; 144, 14%; 76, 53%; 62, 70%; 46, 100%, NO2; 30, 100%, NO. The IR spectrum of compound (1) is close to the IR spectrum of its closest analogue (2) [Zhong Huan Lin, Synthesis and Characterization of High EnergeticTetrazole and Furoxan Derivatives, Doctor of Science Thesis, - Inha University College School, Februar 200. - 122p.]: v cm-1, 1610, 1580, 1510, 1450, 1410 (skeletal variations purananooru ring); 1520, 1310 (CNO2); 820 (C-N). The main difference are in the area of 1500-1700 cm-1: there is no intense absorption band 1650 cm-1(C=N→O), reduced the intensity of the band at 1520 cm-1.

The proposed structure of compound (1) is presented in figure 1.

A new high-energy not previously described derivative 1,2,5-oxadiazole (furazan), namely 3,4-bis(4-nitrofurazan-3-yl)-furazan (1), (1)

- which is a trimer 1,2,5-oxadiazole containing two terminal P-nitro;

- which differs from the known 3,4-bis(3-nitrofurazan-4-yl)-furoxan (2) the absence in its structure 1,2,5-oxadiazol-2-oxide (furoxane the first cycle is replaced by 1,2,5-oxadiazolyl (purasinovic) cycle.

Examples of specific performance

Example 1

175 g (10.4 mol) of 50%H2O2add with stirring and external cooling, 250 g of 96% H2SO4(5.0 mol), diluted with 230 g Aceto-nitrile. Then portions of 3-5 g sprinkled at a temperature of 10°C 66 g (0.28 mol) of 3,4-bis(3-aminopyrazine-4-yl)-furazan (3,4-bis(4-amino-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole) (3). After dosing the reaction mass is maintained at this temperature for 30 minutes, then 2 hours at 60°C, cooled to 5°C and separating the precipitated precipitate by filtration. Washing the Ute precipitate with water and dried in air. The resulting product (1) paracrystal izbivaut from methanol. Output 66-70 g (80-85%), tpl.86-87°C.

Example 2

Synthesis is carried out similarly as described in Example 1, but as the source connection using 3,4-bis(3-N-acetylaminofluorene-4-yl)-furazan, 90 g (0.28 mol). Output 66-70 g (80-85%), tpl.86-87°C.

Example 3

Synthesis is carried out similarly as described in Example 1, but as the source connection using 3,4-bis(3-N-propiomelanocortin-4-yl)-furazan, 97 g (0.28 mol). Output 66-70 g (80-85%), tpl.86-87°C.

Heterocyclic compound - 3,4-bis(4-nitrofurazan-3-yl)-furazan formula 1
,
in which two 3-nitrofurazone cycle directly related to hursanova cycle on the provisions of 3.4, as energy-intensive connection.



 

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13 cl, 76 ex, 2 tbl

Azole compounds // 2493154

FIELD: chemistry.

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13 cl, 38 tbl, 159 ex

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19 cl, 1 tbl, 44 ex

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3 cl, 1 tbl, 3 ex

FIELD: chemistry.

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EFFECT: obtaining compounds which can be used for treating and preventing diseases mediated by low glucokinase activity.

21 cl, 1 dwg, 608 ex, 1 tbl

FIELD: organic chemistry, biochemistry, pharmacy.

SUBSTANCE: invention relates to new heterocyclylsulfonyl alkylcarboxylic acids and their derivatives of the general formula (1): or their pharmaceutically acceptable salts, N-oxides or hydrates possessing the inhibitory effect on kinase activity and to the focused library for search of active leader-compounds comprising at least abovementioned compound. In the general formula 91) W represents optionally substituted heterocyclic radical, among them: pyrrole-3-yl, thiophene-2-yl, isooxazole-4-yl, pyrazole-4-yl, imidazole-4-yl, pyridine-3-yl, 1H-2,4-dioxopyrimidine-5-yl, 2,3-dihydro-1H-indole-5-yl, 2,3-dihydro-1H-indole-7-yl, 1,3-dihydro-2-oxoindole-5-yl, 2,3-dioxo-1H-indole-5-yl, 2-oxo-3H-benzoxazole-6-yl, benzothiazole-6-yl, 1H-benzimidazole-5-yl, benzo[1,2,5]oxadiazole-4-yl, benzo[1,2,5]thiadiazole-4-yl, 1,2,3,4-tetrahydroquinoline-6-yl, 3,4-dihydro-2-oxo-1H-quinoline-6-yl, quinoline-8-yl, 1,4-dihydro-2,3-dioxoquinoxaline-6-yl, 3-oxo-4H-benzo[1,4]oxazine-7-yl, 3-oxo-4H-benzo[1,4]thiazine-7-yl, 2,4-dioxo-1H-quinazoline-6-yl, 2,4-dioxo-1,5-dihydrobenzo[b][1,4]diazepine-7-yl or 2,5-dioxo-3,4-dihydrobenzo[b][1,4]diazepine-7-yl; Y represents optionally substituted methylene group; R1 represents chlorine atom, optionally substituted hydroxyl group, optionally substituted amino-group, optionally substituted azaheterocyclyl; n = 1, 2 or 3; or Yn represents carbon atom of optionally substituted (C3-C7)-cycloalkyl or optionally substituted (C4-C7)-heterocyclyl. Also, invention relates to a pharmaceutical composition in form of tablets, capsules or injections placed into pharmaceutically acceptable package.

EFFECT: valuable properties of compounds.

5 cl, 3 sch, 5 tbl, 6 ex

FIELD: organic chemistry, chemical technology, explosive substances.

SUBSTANCE: invention relates to a method for preparing 4,4'-bis-[4-aminofurazan-3-yl-N(O)N-azoxy]-3,3'-azofurazane of the general formula (1):

that is a new thermostable explosive substance with improved exploitation indices. Method for preparing compound of the formula (1) involves treatment of 4,4'-diaminoazoxyfurazane with potassium bromate solution (KBrO3) in hydrochloric acid medium or its mixture with organic acid. Proposed compound can be used as a component of explosive compositions, solid rocket fuels and power-consuming compositions of different designations exploited at elevated temperatures (for example, in blast-hole drilling in depth mines).

EFFECT: improved preparing method, valuable properties of substance.

1 tbl, 2 ex

The invention relates to new inclusion complexes of derivatives of 1,2,5-oxadiazol-2-oxide of General formula I, where1=R2=CN or together with the adjacent carbon atoms form annelirovannymi 3,6-bis(lower alkyl)pyridazin-1,2-dioxideis cycle, polycyclic derivatives of glucopyranose General formula II, where if n= 1, R3fragment 11-oxo-18, 20-Olean-12-EN-29-OIC acid of the formula III, R4=H, R5--D-glucuronidase, R6=R7=H and R8= C(O)OH, or, if n= 7, R3=N, R4and R7- simple connection, R5and R6= H or (CH2CH(CH3)O)mH, where m=1 to 14, and R8=CH2OH or CH2O(CH2CH(CH3)O)mH, where m=1-14, generating nitric oxide and activating the soluble form of guanylate cyclase (RGC), antispasmodic, vasodilator and hypotensive means quick action and platelet aggregation inhibitors, method for their production and pharmaceutical compositions based on

The invention relates to new chemical compounds, in particular derivatives (1,2,3-triazolyl)-1,2,5-oxadiazole General formula I, where R = NH2or< / BR>
and, if R1= N, R2lowest hydroxyalkyl, or, if R1- lower alkyl, lower hydroxyalkyl, aryl, R2= N, the lower hydroxyalkyl or a radical of General formula-C(O)R3where R3= HE, NH2, lower alkyl or lower alkoxyl, potentiating NO-dependent activation of the soluble form of guanylate cyclase (RGC)

FIELD: organic chemistry, chemical technology, explosive substances.

SUBSTANCE: invention relates to a method for preparing 4,4'-bis-[4-aminofurazan-3-yl-N(O)N-azoxy]-3,3'-azofurazane of the general formula (1):

that is a new thermostable explosive substance with improved exploitation indices. Method for preparing compound of the formula (1) involves treatment of 4,4'-diaminoazoxyfurazane with potassium bromate solution (KBrO3) in hydrochloric acid medium or its mixture with organic acid. Proposed compound can be used as a component of explosive compositions, solid rocket fuels and power-consuming compositions of different designations exploited at elevated temperatures (for example, in blast-hole drilling in depth mines).

EFFECT: improved preparing method, valuable properties of substance.

1 tbl, 2 ex

FIELD: organic chemistry, biochemistry, pharmacy.

SUBSTANCE: invention relates to new heterocyclylsulfonyl alkylcarboxylic acids and their derivatives of the general formula (1): or their pharmaceutically acceptable salts, N-oxides or hydrates possessing the inhibitory effect on kinase activity and to the focused library for search of active leader-compounds comprising at least abovementioned compound. In the general formula 91) W represents optionally substituted heterocyclic radical, among them: pyrrole-3-yl, thiophene-2-yl, isooxazole-4-yl, pyrazole-4-yl, imidazole-4-yl, pyridine-3-yl, 1H-2,4-dioxopyrimidine-5-yl, 2,3-dihydro-1H-indole-5-yl, 2,3-dihydro-1H-indole-7-yl, 1,3-dihydro-2-oxoindole-5-yl, 2,3-dioxo-1H-indole-5-yl, 2-oxo-3H-benzoxazole-6-yl, benzothiazole-6-yl, 1H-benzimidazole-5-yl, benzo[1,2,5]oxadiazole-4-yl, benzo[1,2,5]thiadiazole-4-yl, 1,2,3,4-tetrahydroquinoline-6-yl, 3,4-dihydro-2-oxo-1H-quinoline-6-yl, quinoline-8-yl, 1,4-dihydro-2,3-dioxoquinoxaline-6-yl, 3-oxo-4H-benzo[1,4]oxazine-7-yl, 3-oxo-4H-benzo[1,4]thiazine-7-yl, 2,4-dioxo-1H-quinazoline-6-yl, 2,4-dioxo-1,5-dihydrobenzo[b][1,4]diazepine-7-yl or 2,5-dioxo-3,4-dihydrobenzo[b][1,4]diazepine-7-yl; Y represents optionally substituted methylene group; R1 represents chlorine atom, optionally substituted hydroxyl group, optionally substituted amino-group, optionally substituted azaheterocyclyl; n = 1, 2 or 3; or Yn represents carbon atom of optionally substituted (C3-C7)-cycloalkyl or optionally substituted (C4-C7)-heterocyclyl. Also, invention relates to a pharmaceutical composition in form of tablets, capsules or injections placed into pharmaceutically acceptable package.

EFFECT: valuable properties of compounds.

5 cl, 3 sch, 5 tbl, 6 ex

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