A novel synthesis of 1,5-disubstituted fluorinated tetrazoles from 1,1-difluoroazides

Polivanova, A. G.; Shkavrov, S. V.; Churakov, Andrei V.; Lermontov, A. S.; Лермонтов, С. А.

doi:10.1016/j.tetlet.2010.06.016

Cited by 11 publications

(7 citation statements)

References 30 publications

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“…Primary amines react with α,α‐difluorinated azidoalkanes to afford tetrazoles 12 ; the reaction mechanism and scope is shown in Scheme . The amide side products 13 arise from a competitive azido group substitution and hydrolysis …”

Section: Reactivity Of α‐Fluorinated Azidesmentioning

confidence: 99%

Synthesis, Stability and Reactivity of α‐Fluorinated Azidoalkanes

Bakhanovich

Beier

2019

Chemistry A European J

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Organic α‐fluorinated azidoalkanes appeared in the literature for the first time half a century ago. However, for a long time they remained undeveloped and were regarded as chemical curiosities. Recent advances in the preparation of α‐fluorinated azidoalkanes as well as studies on their stability and reactivity opened up their broader synthetic potential for the preparation of valuable fluorinated and non‐fluorinated compounds.

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Section: Reactivity Of α‐Fluorinated Azidesmentioning

confidence: 99%

Synthesis, Stability and Reactivity of α‐Fluorinated Azidoalkanes

Bakhanovich

Beier

2019

Chemistry A European J

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“…Intermediate C hydrolyzed to the corresponding β-enamido triflate 4 in a good yield (Scheme 5). Primary amines react with α,α-difluorinated azido alkanes to afford tetrazoles, 31 important polyazaheterocycles 32 displaying various bioactive properties. 33 Because tetrazoles bearing the difluoromethyl moiety are unknown, we investigated the reaction of azide 1 with primary amines.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Synthesis and Cycloaddition Reactions of 1-Azido-1,1,2,2-tetrafluoroethane

Shaitanova,

Matoušek,

Herentin

et al. 2023

J. Org. Chem.

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A new fluorinated azidoethane1-azido-1,1,2,2-tetrafluoroethanewas prepared in quantitative yield by the addition of an azide anion to tetrafluoroethylene in a protic medium. The title azide was shown to be thermally stable and insensitive to impact. Copper(I)-catalyzed [3 + 2] cycloaddition with alkynes afforded 4-substituted N-tetrafluoroethyl-1,2,3-triazoles which underwent rhodium(II)-catalyzed transannulation with nitriles to novel N-tetrafluoroethylimidazoles or the reaction with triflic acid to enamido triflates. [3 + 2] Cycloaddition of the title azide with primary amines afforded novel 5-difluoromethyl tetrazoles.

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“…研究表明, 原甲酸乙酯参与制备四唑化合物的反应均具有如下的类似反应机理(Scheme 7). 二氟叠氮化物具有良好的安全稳定性, 可与伯胺在室温下反应来制备含氟的 1,5-二取代四唑类化合物 22 (Scheme 8) [44] . [46] .…”

Section: S Meunclassified

“…重氮盐 29 与腙类化合物 30 反应也可制备四唑化合物 31, 产率可达 81% (Eq. 13) [49] . 该方法需低温控制, 但通过这一反应可有效地实现用四唑环修饰香豆素以得到特殊生物活性的分子.…”

Section: Scheme 10unclassified

Recent Advances in the Synthesis and Application of Tetrazoles

Cui¹,

Damu²,

Guri³

et al. 2013

Chin. J. Org. Chem.

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Tetrazole is an important five-membered aromatic heterocycle with poly-nitrogen electron-rich planar structural feature. This unique structure endows tetrazole derivatives as drugs, explosives, functional materials etc. to exhibit wide potential applications in medicinal, agrochemical, material science and so on. Relevant researches have been becoming active and some important achievements have been made. Based our work on azoles and referring to other literature in recent 5 years, this review systematically summarized the recent advances in the synthesis of tetrazole compounds and their application researches as medicinal drugs, agrochemicals and materials.

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A novel synthesis of 1,5-disubstituted fluorinated tetrazoles from 1,1-difluoroazides

Cited by 11 publications

References 30 publications

Synthesis, Stability and Reactivity of α‐Fluorinated Azidoalkanes

Synthesis, Stability and Reactivity of α‐Fluorinated Azidoalkanes

Synthesis and Cycloaddition Reactions of 1-Azido-1,1,2,2-tetrafluoroethane

Recent Advances in the Synthesis and Application of Tetrazoles

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