Polynuclear nonfused bis(1,3,4-oxadiazole)-containing systems

Vereshchagin, L. I.; Petrov, Andrey V.; Kizhnyaev, V. N.; Pokatilov, F. A.; Смирнов, А. И.

doi:10.1134/s1070428006070219

Cited by 16 publications

(8 citation statements)

References 6 publications

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“…Compound 2 9 was synthesised using a convenient literature method for the formation of bi‐1,3,4‐oxadiazoles. The conversion of bi‐5,5′‐tetrazoles into the oxadiazoles with formation of N 2 results in very high yields (93 %) and a high purity of the target compound 10…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Characterisation and Crystal Structures of Two Bi‐oxadiazole Derivatives Featuring the Trifluoromethyl Group

Kettner

Klapötke

Witkowski

et al. 2015

Chemistry A European J

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The synthesis, characterisation, and crystal structure determination of the closely related compounds 3,3'-bi-(5-trifluoromethyl-1,2,4-oxadiazole) and 5,5'-bi-(2-trifluoromethyl-1,3,4-oxadiazole) are reported. These two compounds are known for their bioactivity; however, in this study they serve as model compounds to evaluate the suitability of the heterocyclic oxadiazole ring system for energetic materials when the fluorine atoms in the exocyclic CF3 groups are substituted successively by nitro groups. Quantum chemical calculations for the bi-1,3,4-oxadiazole derivatives with difluoronitromethyl, fluorodinitromethyl, and trinitromethyl groups have been carried out and predict promising energetic performances for both explosive and propulsive applications.

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Section: Methodsmentioning

confidence: 99%

Synthesis, Characterisation and Crystal Structures of Two Bi‐oxadiazole Derivatives Featuring the Trifluoromethyl Group

Kettner

Klapötke

Witkowski

et al. 2015

Chemistry A European J

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“…Experimental 5-Chloromethyltetrazole (1 g, 8.4 mmol), synthesized from chloroacetonitrile, sodium azide and aluminium chloride according to the method reported by Vereshchagin et al (2006), was dissolved in 25% aqueous ammonia (5 ml). The resulting solution was kept at room temperature for 1 d and evaporated under vacuum.…”

Section: Figurementioning

confidence: 99%

A tetrazol-5-yl analogue of glycine, 5-ammoniomethyl-1H-tetrazolide, and its copper(II) complex

et al. 2010

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A nonclassical tetrazole isostere of glycine, viz. zwitterionic 5-ammoniomethyl-1H-tetrazolide, C(2)H(5)N(5), (I), crystallizes in the chiral P3(1) space group, similar to gamma-glycine. The crystal packing of (I) is determined by a set of classical hydrogen bonds, forming a three-dimensional network that is practically the same as that in gamma-glycine. The Cu(II) complex of (I), poly[[bis(mu(2)-5-aminomethyl-1H-tetrazolido-kappa(3)N(1),N(5):N(4))copper(II)] dihydrate], {[Cu(C(2)H(4)N(5))(2)].2H(2)O}(n), (II), is a layered coordination polymer formed as a result of tetrazole ring bridges. The Cu(II) cations lie on inversion centres, are surrounded by four anions and adopt elongated octahedral coordination. Water molecules are located in the interlayer space and connect the layers into a three-dimensional network via a system of hydrogen bonds.

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“…The same reaction strategy was also applied to N - H -tetrazolo-5-methylamine, 25 , 26 as analogously to the report of Ley et al 27 ( Scheme 3 a) but no product could be isolated. However, we could synthesize a similar product (5) by acidic cleavage of the N - tert -octyl group of the intermediate Ugi adducts ( 14d ).…”

mentioning

confidence: 93%

Library-to-Library Synthesis of Highly Substituted α-Aminomethyl Tetrazoles via Ugi Reaction

et al. 2018

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α-Aminomethyl tetrazoles, recently made accessible by an Ugi multicomponent reaction (MCR), were shown to be excellent starting materials for a further Ugi MCR, yielding substituted N-methyl-2-(((1-methyl-1H-tetrazol-5-yl)methyl)amino)acetamides having four points of diversity in a library-to-library approach. The scope and limitations of the two-step sequence was explored by conducting more than 50 reactions. Irrespective of electron-rich and electron-deficient oxo-components and the nature of the isocyanide component, the reactions give excellent yields. Sterically less hindered α-aminomethyl tetrazoles give better yields of in further Ugi MCR. The target scaffold has four points of diversity and is finding applications to fill screening decks for high-throughput screening (HTS) in the European Lead Factory and in structure-based drug design.

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Polynuclear nonfused bis(1,3,4-oxadiazole)-containing systems

Cited by 16 publications

References 6 publications

Synthesis, Characterisation and Crystal Structures of Two Bi‐oxadiazole Derivatives Featuring the Trifluoromethyl Group

Synthesis, Characterisation and Crystal Structures of Two Bi‐oxadiazole Derivatives Featuring the Trifluoromethyl Group

A tetrazol-5-yl analogue of glycine, 5-ammoniomethyl-1H-tetrazolide, and its copper(II) complex

Library-to-Library Synthesis of Highly Substituted α-Aminomethyl Tetrazoles via Ugi Reaction

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