An efficient access to (1H-tetrazol-5-yl)furoxan ammonium salts via a two-step dehydration/[3+2]-cycloaddition strategy

Ферштат, Леонид Л.; Epishina, Margarita A.; Kulikov, Alexander S.; Овчинников, И. В.; Ananyev, Ivan V.; Махова, Нина Н.

doi:10.1016/j.tet.2015.07.034

Cited by 60 publications

(26 citation statements)

References 85 publications

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“…The structure of compound 8 was further confirmed by X‐ray diffraction study of a crystallohydrate grown from water (Figure ). The structures of the salt's components are very similar to those in the previously published results . The notable intermolecular interactions in crystallohydrate 8⋅ H 2 O are hydrogen bonds and stacking interactions, which provide a layer‐type packing (Figures and S1, Supporting Information) that is, according to CSD, a general motif for salts of tetrazolylfuroxans with planar cations.…”

Section: Resultssupporting

confidence: 81%

“…Azidofuroxan 2 a and azofuroxan 2 b were synthesized on the basis of amino group transformations. A tandem dehydration/[3+2] cycloaddition sequence afforded tetrazolylfuroxan ammonium salts 3 a,b according to our recently developed procedure . Although ammonium salts 3 a,b have previously been reported, their full physical and detonation properties were not studied.…”

Section: Resultsmentioning

confidence: 99%

“…All standard reagents were purchased from Aldrich or Acros Organics and used without further purification. Tetrazolylfuroxan ammonium salts 3 a,b were synthesized according to a described procedure …”

Section: Methodsmentioning

confidence: 99%

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Assembly of Tetrazolylfuroxan Organic Salts: Multipurpose Green Energetic Materials with High Enthalpies of Formation and Excellent Detonation Performance

Larin

Muravyev

Пивкина

et al. 2019

Chemistry A European J

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A series of highly energetic organic salts comprising a tetrazolylfuroxan anion, explosophoric azido or azo functionalities, and nitrogen‐rich cations were synthesized by simple, efficient, and scalable chemical routes. These energetic materials were fully characterized by IR and multinuclear NMR (1H, 13C, 14N, 15N) spectroscopy, elemental analysis, and differential scanning calorimetry (DSC). Additionally, the structure of an energetic salt consisting of an azidotetrazolylfuroxan anion and a 3,6,7‐triamino‐7H‐[1,2,4]triazolo[4,3‐b][1,2,4]triazolium cation was confirmed by single‐crystal X‐ray diffraction. The synthesized compounds exhibit good experimental densities (1.57–1.71 g cm−3), very high enthalpies of formation (818–1363 kJ mol−1), and, as a result, excellent detonation performance (detonation velocities 7.54–8.26 kms−1 and detonation pressures 23.4–29.3 GPa). Most of the synthesized energetic salts have moderate sensitivity toward impact and friction, which makes them promising candidates for a variety of energetic applications. At the same time, three compounds have impact sensitivity on the primary explosives level (1.5–2.7 J). These results along with high detonation parameters and high nitrogen contents (66.0–70.2 %) indicate that these three compounds may serve as potential environmentally friendly alternatives to lead‐based primary explosives.

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Section: Resultssupporting

confidence: 81%

Section: Resultsmentioning

confidence: 99%

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Assembly of Tetrazolylfuroxan Organic Salts: Multipurpose Green Energetic Materials with High Enthalpies of Formation and Excellent Detonation Performance

Larin

Muravyev

Пивкина

et al. 2019

Chemistry A European J

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“… Synthesis of phenylfuroxan derivatives . Reagents and conditions : a) NaCH(NO 2 ) 2 , DMF, 0–5 °C, 24 h; b) H 2 SO 4 , 8–10 °C, then AcOK, MeOH, 8–10 °C, 1 h, 82 %; c) NaNO 2 , AcOK, AcOH, 15–20 °C, 15 min, 74 %; d) TFAA, Py, CH 2 Cl 2 , 0–5 °C, 30 min, then RT, 3 h, 91 %.…”

Section: Synthesis No‐donor Properties and Pharmacological Activitmentioning

confidence: 99%

Molecular Hybridization Tools in the Development of Furoxan‐Based NO‐Donor Prodrugs

Ферштат

Махова

2017

ChemMedChem

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The molecular hybridization of different compounds with known pharmacological activity is a particularly prominent approach for the design of potential drugs with improved pharmacokinetic profiles. Much attention over the last decade has been focused on the synthesis of hybrid structures with a nitric oxide (NO)-donor framework, as NO is a ubiquitous and crucial regulator of cellular metabolism, affecting various physiological and pathophysiological processes. 1,2,5-Oxadiazole 2-oxides (furoxans), which are capable of exogenous NO release in the presence of thiol cofactors, are an important class of prospective NO donors. As such, a wide range of hybrid compounds that combine a furoxan ring with various pharmacologically active structures have been created. This review focuses on recent results in the synthesis and pharmacological activity of furoxan-based hybrids. Special attention is given to chemo- and regioselective methods used in the preparation of these hybrid structures, and the role of synergistic effects on their pharmacological activity, associated with the furoxan fragment.

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“…On the one hand they are of interest as high energy compounds due to a positive enthalpy of formation and the presence of two active oxygen atoms in the molecule. [5][6][7][8][9][10][11][12] On the other hand furoxan derivatives reveal a wide spectrum of pharmacological activity owing to their ability to release NO under physiological conditions. [13][14][15][16][17][18][19] Our last developments resulted in new, effective one-pot approaches for the synthesis of a series of hybrid heterocyclic systems incorporating furoxan ring connected with various pharmacophoric and/or energy rich poly-nitrogen (nitrogen-oxygen) heterocycles (isomeric 1,2,3-and 1,2,4-triazoles, 1,2,4-and 1,3,4-oxadiazoles, tetrazole, pyridines, tetrahydroisoquinoline, indenopyridine, etc.).…”

Section: Introductionmentioning

confidence: 99%

Lewis acid-catalyzed Wolff cyclocondensation in the synthesis of (1H-1,2,3-triazolyl)furoxans

Ферштат¹,

Radzhabov²,

Romanova³

et al. 2017

Arkivoc

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An efficient access to (1H-tetrazol-5-yl)furoxan ammonium salts via a two-step dehydration/[3+2]-cycloaddition strategy

Cited by 60 publications

References 85 publications

Assembly of Tetrazolylfuroxan Organic Salts: Multipurpose Green Energetic Materials with High Enthalpies of Formation and Excellent Detonation Performance

Assembly of Tetrazolylfuroxan Organic Salts: Multipurpose Green Energetic Materials with High Enthalpies of Formation and Excellent Detonation Performance

Molecular Hybridization Tools in the Development of Furoxan‐Based NO‐Donor Prodrugs

Lewis acid-catalyzed Wolff cyclocondensation in the synthesis of (1H-1,2,3-triazolyl)furoxans

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