Aromatische Diazo- und Azoverbindungen XXIX. Darstellung des Tritriazolobenzols und seiner Derivate

Chmátal, V.; Allan, Z. J.; Mužík, F.

doi:10.1135/cccc19590484

Cited by 7 publications

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“…The structures of the tris(triazolo)benzene and its derivatives are supported by IR, 1 H, 13 C NMR and, in some cases, 15 N NMR spectroscopic data as well as elemental analysis (or high-resolution mass spectrometry, HRMS). The 13 C NMR spectra of 8 showed only a single peak at 132 ppm in [D 6 ]DMSO (dimethylsulfoxide), which suggests that the hydrogen is shifting from the N1 to the N3 nitrogen atom of the triazole rings of tris(triazolo)benzene.…”

Section: Methodsmentioning

confidence: 99%

“…Metal salts (9, 10 and 11) and N-substituted nitro (13) and chloro (14) derivatives of 8 were synthesized in high yields. Metal salts (9, 10 and 11) and N-substituted nitro (13) and chloro (14) derivatives of 8 were synthesized in high yields.…”

Section: Methodsmentioning

confidence: 99%

“…Oxidizers provide the oxygen needed for oxidation of the fuel to provide the necessary thrust. [12] In 1959, Muzik, et al described the tris(alkyltriazolo)benzene ring system [13] and in 1993, Samsonov, et al reported the synthesis of unsubstituted tris(triazolo)benzene starting from 1,3,5-triaminobenzene trihydrochloride. [7] One recent focus in energetic materials research is the synthesis of fused cyclic nitrogen-containing heterocycles.…”

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Tris(triazolo)benzene and Its Derivatives: High‐Density Energetic Materials

et al. 2012

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Tris(triazolo)benzene and Its Derivatives: High‐Density Energetic Materials

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“…Tris(triazolo)benzene could be such a type of molecule with three triazole units fused into one benzene ring; a ring system having the advantage of being rich in nitrogen, as well as having high thermal tolerance. [12] In 1959, Muzik, et al described the tris(alkyltriazolo)benzene ring system [13] and in 1993, Samsonov, et al reported the synthesis of unsubstituted tris(triazolo)benzene starting from 1,3,5-triaminobenzene trihydrochloride. [14] However, in the recent literature, to the best of our knowledge there is no report related to the synthesis of tris(triazolo)benzene, none of its N-functionalized derivatives are known, and their utility as possible high-nitrogen energetic materials has not been explored.…”

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confidence: 99%

“…Pure 3,5-dinitroaniline was isolated and was hydrogenated in THF in the presence of 10 % Pd/C under an hydrogen atmosphere (5 atm), to produce 1,3,5-triaminobenzene (3) (Scheme 1). [15] With pure 1,3,5-triaminobenzene in hand rather than making the trihydrochloride salt and subsequently neutralizing using pyridine before adding to diazotized aniline, [13] we directly added 3 to the diazotized aniline derivatives, resulting in a good yield of diazotized product. Among anilines, pnitroaniline produced the best results in the diazo-coupling reactions.…”

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Tris(triazolo)benzene and Its Derivatives: High‐Density Energetic Materials

et al. 2012

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High-performance explosives: Tris(triazolo)benzene was synthesized and converted to its trinitro and trichloro derivatives (see scheme; R=NO(2), Cl). The heats of formation of this "high-nitrogen" compounds were calculated and combined with experimentally determined densities to determine detonation pressures and velocities. They exhibit high density, good thermal stability, high heats of formation, and moderate to good detonation properties.

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Benzenepentamine – Its Easy Accessibility and Use in Syntheses of Pyrazinoquinoxalines

et al. 1989

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Bcnncncpentarnine (6) has been rediscoverud alter about 60 years. A sirnplc and very emcient synthctic route is described which yiclds the very sensitive, colourless 6 in mcthanolic solution in ncarly quantitative yield. Condcnsations or 6 with two masked forms A and B of glyoxal convenicntly lead to two typcs or amino-substih~ted pyra7.inoquinoxalincs. onc with an nngular phcnmthrcnc-type ropology (7a). or one with thc linear anthraccnc-typc structure @a), respectively. with avccptable yields. The r-tiiketone b e n d also reacts with 6, bu1 lcss wleclively. forming thc corresponding terraphenyl derivatives 7b an 8b ol both these hcicrcrtricyclic ring systems. Thc hcretolore unknown nitrobenzenepcntaminc (9). forrncd in addition to bcnzcnehexamine in rcduction rcactions of I.3.5-trinitrobcnxcnctriamine, has also h e n obtained. Based on spectroscopic data, the structures of these two multiamines have been deduced From their condensation products with n-diketones, in the case of the ncw penpamine 9 From its first derivatives 7c -e of pyrazino[2.3~~quinoxaliuv.Benzenehexamine having been studied2-6) very rarely in the past and neglected for almost 50 years is now readily acce~sible'~~) by Birch reduction of 1,3,5-trinitrobenzenetriamine. Previous work from both our laboratorie~~-~) has shown that benzenehexamine can be condensed with various a-diketones*-') and also with masked forms of glyoxa12) (e.g. A*) and B9)) to give numerous derivatives of dipyrazino[2,3-f2',3'-h]quinoxaline(1,4,5,8,9,12-hexaazatriphenylene) 2-4,10) or its parent heteroring system2), respectively, in good yields. This approach proved to be a considerable improvement over an earlier, long, and inefficient 10-step synthesis of the parent dipyrazinoquinoxaline and makes this interesting tetracyclic molecule now readily available for further studies as a ligand for transition metals and as a fundamental building block for compounds with either noncalamitic liquid-crystalline or potential ferromagnetic properties.On the other hand, benzenepentamine (6), the foregoing member of this series of multiamines, has been mentioned 12), prepared from 1,3,5-trinitrobenzenediamine (3) by reduction with tin in hydrochloric acidI3), and even applied to first condensation reactions 13) with carbonyl compounds already in the last century14). With the exception of another synthesis of 6 in which 3 has been reduced with the ' ' Deceased on November 30. 1988. hazardous phenylhydrazine exactly 60 years ago"), 6 was completely forgotten. Our work on N-heterocycles drew our attention also to this interesting multiamine 6 since it should, for instance, allow simple one-pot syntheses of a variety of amino-substituted tetraaza multicyclic aromatic compounds of manifold interest. It was thus necessary to develop a more efficient synthesis of benzenepentamine (6), which indeed could be realized on the basis of the experience gained during our former work on benzenehexamine 2-s,10!The best way to get to benzenepentamine (6) is outlined in Scheme 1. It starts from commercia...

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Aromatische Diazo- und Azoverbindungen XXIX. Darstellung des Tritriazolobenzols und seiner Derivate

Cited by 7 publications

References 0 publications

Tris(triazolo)benzene and Its Derivatives: High‐Density Energetic Materials

Tris(triazolo)benzene and Its Derivatives: High‐Density Energetic Materials

Tris(triazolo)benzene and Its Derivatives: High‐Density Energetic Materials

Benzenepentamine – Its Easy Accessibility and Use in Syntheses of Pyrazinoquinoxalines

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