ChemInform Abstract: 3′‐(Tetrazol‐2‐yl)‐2′,3′‐dideoxythymidine.

Островский, В. А.; Ivanova, N. V.; Malin, A. A.; Shcherbinin, M. B.; Poplavskii, V. S.; Studentsov, E. P.

doi:10.1002/chin.199445234

ChemInform

1994

DOI: 10.1002/chin.199445234

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ChemInform Abstract: 3′‐(Tetrazol‐2‐yl)‐2′,3′‐dideoxythymidine.

В. А. Островский¹,

N. V. Ivanova²,

A. A. Malin³

et al.

Abstract: 1994 nucleic acids nucleic acids U 0700 45 -234 3'-(Tetrazol-2-yl)-2',3'-dideoxythymidine. -The title compound (III) is prepared in order to test its biological activity. -(OSTROVSKII, V. A.; IVANOVA, N. V.; MALIN, A. A.; SHCHERBININ, M. B.; POPLAVSKII, V. S.; STUDENTSOV, E. P.; Zh.

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“…Only under this condition the selective exhaustive alkylation should occur giving tetrazolide VI. In keeping with the known [14] indices of the acidity constants in water of the tetrazole ring of compound IV (pK a 3.39) and the basicity constant of the terminal dimethylamino group (pK BH + 9.39) it is presumable that in the course of alkylation the pH >10.5 should be maintained. Secondly, the important condition of the selective exhaustive alkylation is the reagents ratio.…”

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Vinyltetrazoles: I. Synthesis of NH-unsubstituted 5-vinyltetrazole

et al. 2010

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The NH-unsubstituted 5-vinyltetrazole was obtained in 55% yield by exhaustive methylation of 5-(β-dimethylaminoethyl)tetrazole with dimethyl sulfate at the terminal dimethylamino group with the subsequent elimination of a proton from the α-CH 2 group and Hofmann β-cleavage of the intermediate 5-(β-trimethylammoniumethyl)tetrazolide methyl sulfate. The microwave irradiation was shown to reduce 5-fold the time of the synthesis of the initial substrate, 5-(β-dimethylaminoethyl)tetrazole.NH-Unsubstituted 5-vinyltetrazole (I) and its alkyl derivatives, e.g., II and III, have a considerable practical interest as substrates for preparation of polymers with a high nitrogen content, poly(vinyl-5-yltetrazoles) [1]. These polymers and materials based thereon are required by to-day medicine and engineering [2]. The poly(vinyl-5-yltetrazoles) can underlie the fi lter materials for the purifi cation of the biological fl uids from heavy metal ions and radionuclides [3], superabsorbents of moisture [4], effi cient energy-rich materials [5].Up till now only few chemical reactions of NHunsubstituted 5-vinyltetrazole (I) are known at the endocyclic nitrogen atoms. Arnold and Thatcher showed that the acylation of 5-vinyltetrazole (I) with acetic anhydride followed by the thermolysis of the intermediate N-acyl derivative occurring with elimination of a nitrogen molecule led to the formation of 2-methyl-5-vinyl-1,3,4-oxadiazole [6]. The reaction of 5-vinyltetrazoles I-III with PdCl 2 resulted in the formation of coordination compounds of the general formula PdL 2 Cl 2 [7]. On replacing in these processes palladium chloride with CuCl 2 or NiCl 2 the arising coordination compounds do not contain chlorine in their composition. Therefore Kizhnyaev and Kruglova [7] suggest that here the ligand is the corresponding anionic form 5-vinyltetrazolide. In [8] the rate constants were measured of tetrazole I alkylation with methyl iodide in acetonitrile in the presence of triethylamine, and the ratio was established of isomeric reaction products, 1-(II) and 2-methyl-5-vinyltetrazoles (III). The reactions involving the vinyl group of tetrazole I save the polymerization processes [1] are virtually unknown notwithstanding the obvious possibility to obtain in this way new promising compounds. The development of research in this fi eld of the tetrazole chemistry is hampered by the limited availability of the initial compound, NH-unsubstituted 5-vinyltetrazole (I). Evidently the development of an effi cient procedure of the synthesis of NH-unsubstituted 5-vinyltetrazole (I) is an urgent task.The most wide-spread preparation method for NHunsubstituted 5-R-tetrazoles is the 1,3-dipolar cycloaddition of azides to nitriles. Recently versatile versions of this process were developed permitting the preparation of various 5-R-tetrazoles (R = Alk, Ar, Ht) in good yield and under relatively mild conditions [3]. However the only example of the synthesis of NH-unsubstituted 5-vinyltetrazole (I) directly from acrylonitrile was reported

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“…5-(β-Dimethylaminoethyl)tetrazole (IV) was prepared as previously published in [14], by the 1,3-dipolar cycloaddition of dimethylammonium azide to β-dimethylaminopropionitrile. This method is simple in performing, relatively safe, and the necessary reagents are fairly available.…”

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Vinyltetrazoles: I. Synthesis of NH-unsubstituted 5-vinyltetrazole

et al. 2010

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ChemInform Abstract: 3′‐(Tetrazol‐2‐yl)‐2′,3′‐dideoxythymidine.

Abstract: 1994 nucleic acids nucleic acids U 0700 45 -234 3'-(Tetrazol-2-yl)-2',3'-dideoxythymidine. -The title compound (III) is prepared in order to test its biological activity. -(OSTROVSKII, V. A.; IVANOVA, N. V.; MALIN, A. A.; SHCHERBININ, M. B.; POPLAVSKII, V. S.; STUDENTSOV, E. P.; Zh.

Cited by 1 publication

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Vinyltetrazoles: I. Synthesis of NH-unsubstituted 5-vinyltetrazole

Vinyltetrazoles: I. Synthesis of NH-unsubstituted 5-vinyltetrazole

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