The reactivity and mechanism of action of triazenes (review)

Nifontov, V. I.; Belskaya, Nataliya P.; Shtokareva, E. A.

doi:10.1007/bf02219299

Cited by 3 publications

(2 citation statements)

References 186 publications

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“…Aryltriazenes are safely and mostly readily prepared by the coupling of diazotized aniline with amine, or by the action of Grignard reagents on aryl azides [79], and can be stored for a long period of time in cold temperatures protected from light. They are adaptable to numerous synthetic transformations with wide applicability in the chemical, medical, and technological fields [80,81]. An essential advantage over aryldiazonium ions (Balz-Schiemann reaction) is their solubility in a number of (anhydrous) organic and ionic solvents that allows in situ generation of the corresponding aryldiazonium ion upon reacting with acids, and therefore enabling a one-pot fluoro-detriazenation reaction [60,82].…”

Section: Radiofluorination Of Electron-rich Arenes By Wallach Reactionmentioning

confidence: 99%

18F-Labeled Aryl-Tracers through Direct Introduction of [18F]fluoride into Electron-Rich Arenes

Kovač¹,

Mavel²,

Anderluh

2013

COC

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Rapid and efficient methods using no-carried-added [ 18 F]fluoride as the source of fluorine-18 for nucleophilic aromatic fluorination play an important role in the development of new radiopharmaceuticals for positron emission tomography (PET). Molecules that bear electron-rich aromatic moieties are especially difficult to label by direct single-step nucleophilic no-carrier-added radiofluorination. Classical Balz-Schiemann reaction with its modifications, Wallach reaction and diaryliodonium salts methodology are a few methods to enable this. The present review provides a critical overview of these chemical methods with the emphasis on diaryliodonium salt as precursors for the direct introduction of [ 18 F]fluoride into electron-rich arenes in synthesis of 18 F-labeled molecules for PET scanning.

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Section: Radiofluorination Of Electron-rich Arenes By Wallach Reactionmentioning

confidence: 99%

18F-Labeled Aryl-Tracers through Direct Introduction of [18F]fluoride into Electron-Rich Arenes

Kovač¹,

Mavel²,

Anderluh

2013

COC

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“…On the other hand, the chemistry of triazenes [Ar‐N=N‐NR 2 ], and their antitumor activity have received much attention [ 14‐19] . A number of triazenes have been found to possess antibacterial, analgesic, antiviral, antimalarial, antitumor and cytotoxic activity . In addition, triazenes are used as ligands in the synthesis of metal complexes,‐ and as reagents for spectrophotometric determination of transition metals…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Novel Tetrahydro‐1,2,4‐triazines Incorporating Triazene and Tetraazene Moieties

2019

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Diazotization of the hydrazone (2), derived from 6‐Acetyl‐2,4‐diphenyl‐tetrahydro‐1,2,4‐triazine (1), gave the corresponding 1‐chlorotriaz‐2‐enylidene derivative 3. Coupling of 3 with resorcinol and 2‐naphthol afforded the triazenes 4 and 5. The synthesis of tetrahydro‐1,2,4‐triazine incorporating triazene and piperidine or piperazine moieties has been achieved by coupling of 3 with the respective amine. Coupling of 3 with aromatic amines and polyhydroxy amines gave the corresponding tetraazenes. Whereas, coupling with the hydrazone 2 afforded pentaazene. In addition, the coupling of aryl diazonium salts with the hydrazone 2 was investigated.

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