Tetrazoles

Островский, В. А.; Koldobskii, G. I.; Trifonov, R. E.

doi:10.1016/b978-008044992-0.00517-4

Cited by 136 publications

(75 citation statements)

References 642 publications

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“…1 Beginning from the 1960s chemists are searching for efficient methods of syn thesis of N alkyl 5 vinyltetrazoles. 2 This search is imped ed by numerous quantitative studies of key chemical pro cesses resulting in 5 vinyltetrazole derivatives.…”

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confidence: 99%

Kinetics and mechanism of formation of isomeric 1-methyl- and 2-methyl-5-vinyltetrazoles

et al. 2009

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The alkylation of 5 (β dimethylaminoethyl)tetrazole (1) with dimethyl sulfate afforded 5 (β dimethylaminoethyl) 1 methyltetrazole (2) and 5 (β dimethylaminoethyl) 2 methyltetr azole (3). The exhaustive alkylation of compounds 2 and 3 at the terminal dimethylamino group gave 1 methyl (4) and 2 methyl 5 (β trimethylammonioethyl)tetrazole (5) methyl sul fates. The proton elimination from the α methylene (with respect to the tetrazole cycle) groups of the quaternary ammonium cations of salts 4 and 5 by the action of a base leads to the corresponding zwitterions 4 ± and 5 ± , which in the rate determining step undergo the cleavage of the nitrogen-carbon bond with the formation of 1 methyl 5 vinyl (6) and 2 methyl 5 vinyltetrazole (7). The true constant of the transformation of zwitterion 4 ± into tetrazole 6 is 21 times higher than that for the transformation of zwitterion 5 ± into tetrazole 7.Key words: 1 methyl 5 vinyltetrazole, 2 methyl 5 vinyltetrazole, kinetics of formation, deamination mechanism.Isomeric N alkyl 5 vinyltetrazoles are initial mono mers in the synthesis of the corresponding poly(vinyl tetrazoles), which are promising high energy polymers with a series of unique properties. 1 Beginning from the 1960s chemists are searching for efficient methods of syn thesis of N alkyl 5 vinyltetrazoles. 2 This search is imped ed by numerous quantitative studies of key chemical pro cesses resulting in 5 vinyltetrazole derivatives. The results on studying the kinetics of alkylation of NH unsubstituted 5 vinyltetrazole with methyl iodide in an acetonitrile me dium in the presence of triethylamine have recently 3 been published. The hypothetical mechanism was formulated 3 and the boundaries for changing the reaction conditions, which allow one to control the rate and selectivity of alky lation in certain limits, were determined. However, since the initial substrate is NH unsubstituted 5 vinyltetrazole is a hardly accessible compound yet, the patented method for the preparation of N alkyl 5 vinyltetrazoles based on the synthesis and subsequent alkylation of 5 (β dimethyl aminoethyl)tetrazole with dimethyl sulfate in an aqueous medium in the presence of alkaline metal hydroxide seems more promising. 4,5 The variants of this method described in the cited patents are almost identical and only differ by the nature of the base used: NaOH (see Ref. 4) and KOH (see Ref. 5), respectively. Let us consider the hypothetical sequence of the synthesis of isomeric N methyl 5 vinyltetr azoles postulated in the patents 4,5 (Scheme 1).Isomeric vinyltetrazoles 6 and 7 are formed due to the deamination of intermediate quaternary ammonium salts Scheme 1

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Kinetics and mechanism of formation of isomeric 1-methyl- and 2-methyl-5-vinyltetrazoles

et al. 2009

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“…In our opinion, a simpler and more effective method for the synthesis of similar compounds is the traditional approach to the construction of N(1)-substituted tetrazole rings, based on the interaction of aromatic amines with sodium azide and orthoesters in acetic acid. 31 We found that the heating the aminopyrazoles 1 in acetic acid with sodium azide and triethyl orthoformate or triethyl orthoacetate for 4 h at 90°С resulted in a complete conversion of the starting aminopyrazoles (Scheme 1). The target 1-pyrazolyltetrazoles 2a-d, 3a, and 4a-c were obtained in 55-80% yields.…”

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confidence: 98%

“…The selection of tetrazole molecule as a heterocyclic carrier of N-nitropyrazole substituent was based on the biological activity of tetrazole derivatives, second only to imidazoles according to the number of publications in the field of medicinal chemistry. [31][32] The simplest and most effective method for the introduction of N-nitro group in pyrazole ring, which has been used most frequently for the preparation of N-nitropyrazoles, is the N-nitration of N-unsubstituted 1Н-pyrazoles. [12][13][14] However, only one N-unsubstituted 1-pyrazolyltetrazole has been described in the literature, 1-(1Н-pyrazol-3(5)-yl)-1Н-tetrazole, 33 obtained in 3(5)-diazopyrazole reaction with diazomethane.…”

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Synthesis of 1-(N-nitropyrazolyl)-1Н-tetrazoles – a new type of heteronuclear N-nitropyrazole derivatives

Вацадзе

Serushkina

Дутов

et al. 2015

Chem Heterocycl Comp

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“…Two nitrogen molecules and large amount of energy has liberated by the decomposition of tetrazole due to its high enthalpy formation. Therefore, derivatives of tetrazoles are explored as explosives, propellant components and gas generators [18]. In addition, a variety of tetrazole-based moieties has excellent coordination properties and is able to form stable complexes with various metal ions [19,20].…”

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confidence: 99%

ZnBr2-SiO2 catalyzed green synthesis of tetrazoles: Molecular docking and antioxidant activity studies

et al. 2017

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A series of 5-substituted and 1,5-disubstituted tetrazoles were synthesized in high yields from various biologically active substituted nitriles with sodium azide under heterogeneous catalysed (ZnBr2-SiO2) [2+3] cycloaddition conditions. This reaction gave an excellent yield in the presence of catalytic amount of 0.2 g of ZnBr2-SiO2, glycerol solvent system under microwave irradiation conditions. All the prepared compounds were characterized by elemental analysis 1 H NMR, 13 C NMR, FT-IR, and mass spectral data. The newly synthesized compounds were investigated for their respective molecular target using molecular docking studies. The results reveal that compounds 5a, 5c, 5e and 3e have conferred with multi target property. The compounds 5a, 5c and 5e have shown the highest binding affinities of -10.1, -9.7 and -10.6 with reverse transcriptase, -8.5, -8.2 and -8.9 with Aurora B, respectively. The compounds 5a, 5e and 3e have shown -8.9, -8.5 and 8.4 with Aromatase, respectively. In addition, the antioxidant activity data reveals that all the compounds showed good antioxidant activity, particularly the compounds 3d, 5d, and 5e exhibited promising radical scavenging activity.

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Tetrazoles

Cited by 136 publications

References 642 publications

Kinetics and mechanism of formation of isomeric 1-methyl- and 2-methyl-5-vinyltetrazoles

Kinetics and mechanism of formation of isomeric 1-methyl- and 2-methyl-5-vinyltetrazoles

Synthesis of 1-(N-nitropyrazolyl)-1Н-tetrazoles – a new type of heteronuclear N-nitropyrazole derivatives

ZnBr2-SiO2 catalyzed green synthesis of tetrazoles: Molecular docking and antioxidant activity studies

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