Synthesis of 2,4,6-Tris(trinitromethyl)-1,3,5-triazine

Шастин, А. В.; Годовикова, T. И.; Golova, S. P.; Кузьмин, В. С.; Khmel'nitskii, L. I.; Корсунский, Б. Л.

doi:10.1070/mc1995v005n01abeh000440

Cited by 25 publications

(16 citation statements)

References 3 publications

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“…The synthesis of the 2-amino-4,6-bis(trinitromethyl)-l,3,5-triazine I was described in [4], and the synthesis of the 2-trimethylsilylamino-and tert-butylamino-4,6-bis(trinitromethyl)-1,3,5-triazines II and VI was described in [5].…”

Section: Methodsmentioning

confidence: 99%

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Trisubstituted 1,3,5-triazines. 4. Synthesis of 2-nitroamino-4,6-bis(trinitromethyl)-1,3,5-triazine

Шастин¹,

Годовикова²,

Корсунский³

1999

Chem Heterocycl Compd

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Section: Methodsmentioning

confidence: 99%

“…We had previously developed the method used in synthesizing these triazines [5,6]. Numerous attempts at the direct N-nitration of compounds I and II were unsuccessful.…”

mentioning

confidence: 99%

Trisubstituted 1,3,5-triazines. 4. Synthesis of 2-nitroamino-4,6-bis(trinitromethyl)-1,3,5-triazine

Шастин¹,

Годовикова²,

Корсунский³

1999

Chem Heterocycl Compd

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“…The structure of the polydentate anion in 1c may be represented by resonance forms having a single conjugated electronic system. The alkylation might occur at five sites: the exocyclic oxygen atom, N (1) and N (3) of the tetrazole fragment, and N (4) and N (6) of the triazine ring. The alkylation of silver salt 1c by methyl iodide proceeds both in an excess of the alkylating agent and in acetonitrile solution.…”

mentioning

confidence: 99%

Condensed Tetrazolo-1,3,5-triazines. 2. Alkylation and Nucleophilic Substitution of 5-Trinitromethyltetrazolo[1,5-a]-1,3,5-triazin-7-ones

Fedorov

Utienyshev

Ghidaspov

et al. 2005

Chem Heterocycl Compd

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ray diffraction structural analysis of this product was carried out and feasibility was demonstrated for the nucleophilic substitution of the trinitromethyl group in this compound by the action of phenol, phenol derivatives, and thiophenol.Keywords: condensed tetrazolo-1,3,5-triazines, 5-aryloxy-3-methyl-and 5-arylthio-3-methyltetrazolo[1,5-a]-1,3,5-triazin-7-ones, 3-methyl-5-trinitromethyltetrazolo[1,5-a]-1,3,5-triazin-7-one, alkylation, nucleophilic substitution of the trinitromethyl group.In a continuation of a study of condensed tetrazolo-1,3,5-triazines [1], we synthesized covalent derivatives of substituted tetrazolo[1,5-a]-1,3,5-triazin-7-one by the alkylation of various salts of 5-trinitromethyltetrazolo[1,5-a]-1,3,5-triazin-7-one using methyl iodide in DMF and acetonitrile. Alkylation could not be obtained using the tetramethylammonium salt of 5-trinitromethyltetrazolo[1,5-a]-1,3,5-triazin-7-one (1a) [1] despite broad variation of the reaction conditions such as the solvent, reaction temperature, and reaction time. The desired product could be obtained by alkylation only through use of the silver salt of 5-trinitromethyltetrazolo[1,5-a]-1,3,5-triazin-7-one [2].

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“…The synthesis of compound 3a has been reported in [2]. Compound 3b was prepared according to the method reported in [2] using a solution of Et 2 NH in chloroform. Yield 80%; mp 138-139°C (decomp.).…”

mentioning

confidence: 99%

“…

The general method for preparing condensed tetrazoles is based on the annelation of tetrazole to the triazine ring via an azido-tetrazole tautomeric conversion of the azidoazomethine fragment in the molecule [10,11].

…”

mentioning

confidence: 99%

Condensed Tetrazolo-1,3,5-triazines. 1. Synthesis of 5-Polynitromethyltetrazolo[1,5-a]-1,3,5-triazin-7-one Salts

Fedorov

Fadeev

Гидаспов

et al. 2005

Chem Heterocycl Compd

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Investigations of the synthesis and chemical properties of nitro-and polynitromethyl derivatives of 1,3,5-triazine have been actively carried out in recent years [1][2][3][4][5][6][7][8][9]. Our work is also based on a study of the reactivity of trinitromethyl derivatives of 1,3,5-triazine and concerns the potential synthesis of previously unreported polynitromethyltetrazolo-1,3,5-triazines in which a tetrazole ring is annelated to the 1,3,5-triazine ring.The general method for preparing condensed tetrazoles is based on the annelation of tetrazole to the triazine ring via an azido-tetrazole tautomeric conversion of the azidoazomethine fragment in the molecule [10,11]. For azido-1,3,5-triazines which contain electron-donor substitutents this question has been considered in [12,13].NaN 3 3a, 4a R 1 = R 2 = Me; 3b, 4b R 1 = R 2 = Et __________________________________________________________________________________________

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Synthesis of 2,4,6-Tris(trinitromethyl)-1,3,5-triazine

Cited by 25 publications

References 3 publications

Trisubstituted 1,3,5-triazines. 4. Synthesis of 2-nitroamino-4,6-bis(trinitromethyl)-1,3,5-triazine

Trisubstituted 1,3,5-triazines. 4. Synthesis of 2-nitroamino-4,6-bis(trinitromethyl)-1,3,5-triazine

Condensed Tetrazolo-1,3,5-triazines. 2. Alkylation and Nucleophilic Substitution of 5-Trinitromethyltetrazolo[1,5-a]-1,3,5-triazin-7-ones

Condensed Tetrazolo-1,3,5-triazines. 1. Synthesis of 5-Polynitromethyltetrazolo[1,5-a]-1,3,5-triazin-7-one Salts

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