Synthesis of (1,2,3-triazol-1-yl)furazans. 2. Reaction of azidofurazans with morpholinonitroethene

Batog, L. V.; Rozhkov, V. Yu.; Strelenko, Yu. À.; Lebedev, O. V.; Khmel'nitskii, L. I.

doi:10.1007/bf02256874

Cited by 14 publications

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“…In a boiling aqueous solution of NaHCO 3 used in an equi molar amount, the ester group was hydrolyzed to give acid 14 in high yield (see Scheme 4, Tables 1-3); its decarboxylation in boiling AcOH yielded product 2b, which was spectroscopically identical with an authentic sample. 8 A reaction of compound 3a with phenol in boiling EtOH gave substitution product 15 (see Scheme 4, Tables 1-3).…”

Section: Methodsmentioning

confidence: 99%

“…After three days, hydroxymethyl derivative 6a (0.13 g, 72%) was filtered off in the α form. 8 Or ganic material was extracted from the filtrate with AcOEt. The extract was dried with MgSO 4 and evaporated to dryness in vacuo to give compound 6a (0.04 g, 22%) in the β form.…”

Section: Reactions Of Compounds 2a and 2b With Nanmentioning

confidence: 99%

“…Nitro compounds 1a,b and 2c and chloromethyl de rivatives 2a,b have been synthesized earlier. 8,9,12 Tri azolylfurazans 3a-c and 4 have not been described. The synthesis of chlorides 2a,b by cycloaddition of 4 amino 3 azidofurazan (5) to propargyl chloride 8 allowed only one isomer (2a) to be isolated in good yield; for this reason, we employed here an alternative method of pre paring compound 2b.…”

mentioning

confidence: 96%

“…For instance, reactions of nitrofurazans with O and S nucleophiles have been studied 5, 6 and substitution of the N 3 group for chlorine in the CH 2 Cl substituent in the 1,2,3 triazole ring has been reported. 7 Earlier, [8][9][10][11] we have developed methods for the syn thesis of (1,2,3 triazol 1 yl) 1,2,5 oxadiazoles, in which the triazole and furazan rings are linked by the N(1´)-C bond. Some reactions of these compounds (e.g., oxida tion of the NH 2 group at the furazan ring into NO 2 , NO, and N=N groups and transformation of the NH 2 group into an N 3 group via diazotization) were investigated.…”

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confidence: 99%

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Nucleophilic substitution in the series of (1,2,3-triazol-1-yl)-1,2,5-oxadiazoles. Reactions with N-, O-, and S-nucleophiles

2005

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Methods for the synthesis of amino(1,2,3 triazol 1 yl) 1,2,5 oxadiazoles (amino triazolylfurazans) with CH 2 Cl and COCH 2 Br substituents in the triazole ring were developed and nucleophilic substitution for their halogen atom in reactions with N , O , and S nucleo philes were studied. The possibility of displacing the NO 2 group from the furazan and triazole rings in triazolylfurazans by an azido group was investigated. Novel compounds of this series were synthesized; the reaction rate and pathway were found to depend on the nature of the substrate and the reagent and the position of the substituent in isomers.

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Section: Methodsmentioning

confidence: 99%

Section: Reactions Of Compounds 2a and 2b With Nanmentioning

confidence: 99%

mentioning

confidence: 96%

mentioning

confidence: 99%

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Nucleophilic substitution in the series of (1,2,3-triazol-1-yl)-1,2,5-oxadiazoles. Reactions with N-, O-, and S-nucleophiles

2005

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“…In contrast to the diacetate, in reaction with sodium azide in methanol the monoacetate of tetranitrobutanediol (34) forms 5-substituted 4-nitro-1,2,3-triazole, which the authors oxidized with potassium permanganate without isolation to 5-nitro-1,2,3-triazole-4-carboxylic acid (35). Of the cycloaddition reactions of azides to a double bond it is necessary to mention the fairly often employed reaction of organic azides with 1-amino-2-nitroethenes [21,[34][35][36][37][38][39][40][41][42][43], which are usually obtained by the reaction of a secondary amine and nitromethane with orthoesters [42] or of nitromethane with aminoacetals [44]. The cycloaddition of azides to nitroenaminals 36 is accompanied by the elimination of the amine from the intermediate unstable triazoline 37 with retention of the nitro group in the obtained heterocycle 38.…”

Section: Ch Chmentioning

confidence: 99%

Synthesis and properties of nitro-1,2,3-triazoles (Review)

Vereschagin

Pokatilov

Kizhnyaev

2008

Chem Heterocycl Comp

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Published data on methods for the synthesis of substituted 4(5)-nitro-1,2,3-triazoles and their properties are reviewed.Against the background of the extremely large amount of published information about methods for the production of vicinal triazoles and their properties the chemistry of nitro-substituted triazoles of this series is in an embryonic state. At the same time, according to existing data, vicinal nitrotriazoles may find use in the synthesis of medicines, dyes, agents for the struggle against agricultural pests, energy-rich components of propellants, special-purpose powders, and in other regions of technology. However, the practical application of these compounds has been restrained by the lack of technologically convenient methods for their production. Until now sufficiently effective preparative methods have not been developed for their synthesis. With respect to their properties it is known only that the nitro group of the triazoles is capable of being reduced catalytically to an amino group and substituted by various nucleophilic fragments, while the triazole ring is alkylated by alkyl halides and adds to an activated multiple bond. The limited information is probably explained by the poor availability of vicinal nitrotriazoles, which is most likely due to the passivity of the 1,2,3-triazole in electrophilic substitution reactions at carbon atoms and particularly in nitration processes. In this connection it seems expedient to examine methods for the synthesis of nitro-substituted 1,2,3-triazoles by direct nitration with due regard to the conditions determining the entry of the nitro group into the azole ring and also methods for the construction of nitrotriazoles by the cyclization of open-chain nitro compounds and to assess their properties. SYNTHESIS OF NITRO-1,2,3-TRIAZOLES Nitration of 1,2,3-TriazolesThe inertness of the carbon atoms of the triazole ring toward electrophilic reagents is due to distribution of the electron density of the ring in such a way that the carbon atoms carry a partial positive charge, preventing the addition of a nitronium cation. Therefore, the path to direct nitration of the ring of unsubstituted vicinal triazole has not so far been realized. Attempts to introduce a nitro group into the ring of the heterocycle of 1-phenyl-and 4-phenyl-1,2,3-triazoles were unsuccessful. 1-Phenyl-1,2,3-triazole (1) does not form 4(5)-nitrosubstituted triazole during nitration even under rigid conditions. Here, only the phenyl ring is nitrated-initially at the para position and then at the ortho position [1-3].

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ChemInform Abstract: Synthesis of (1,2,3‐Triazol‐1‐yl)furazans. Part 2. Reaction of Azidofurazans with Morpholinonitroethene.

et al. 2000

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Synthesis of (1,2,3-triazol-1-yl)furazans. 2. Reaction of azidofurazans with morpholinonitroethene

Abstract: We have studied the 1,3-dipolar cvcloaddition of azidofi.azans to morpholinonitroethene and prepared 1,2,3-triazoles with furazan ring in position 1 and NO: group at position 4.

Cited by 14 publications

References 3 publications

Nucleophilic substitution in the series of (1,2,3-triazol-1-yl)-1,2,5-oxadiazoles. Reactions with N-, O-, and S-nucleophiles

Nucleophilic substitution in the series of (1,2,3-triazol-1-yl)-1,2,5-oxadiazoles. Reactions with N-, O-, and S-nucleophiles

Synthesis and properties of nitro-1,2,3-triazoles (Review)

ChemInform Abstract: Synthesis of (1,2,3‐Triazol‐1‐yl)furazans. Part 2. Reaction of Azidofurazans with Morpholinonitroethene.

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