NEW N,N′-<i>bis</i>(SUBSTITUTED PHENYLAZO) PIPERAZINES AND THEIR CLEAVAGE REACTIONS IN ACETIC ACID

Yanarateş, Erkan; Dişli, Ali; Yıldırır, Yılmaz

doi:10.1080/00304949909355733

Cited by 19 publications

(14 citation statements)

References 15 publications

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“…The new 1-aryl-4-[aryldiazenyl]-piperazines (2d) have the potential to undergo thermal cleavage under appropriate conditions to provide a route to unsymmetrically substituted N-aryl-N'-arylpiperazines (8). In a previous report [7], it was shown that the synmmetrical 1,4-bis-(2-aryldiazen-1-yl-)piperazines (1) undergo thermal cleavage in acetic acid to afford symmetrical N,N'-diarylpiperazines. The analogous reaction of 2d would afford the unsymmetricaly substituted piperazines (8) thus:…”

Section: Resultsmentioning

confidence: 99%

“…Further investigation led to the synthesis of a large number of 1-(2-aryldiazen-1-yl-)4-acylpiperazines (2c); the paper describing these latter results has recently been published [5]. The next logical step in the pursuit of new molecules of Also the isomer methyl 4-[2-(4-phenethylpiperazino)-1-diazenyl]benzoate (7) has been prepared and characterized.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Characterization of a Series of 1-Aryl-4-[aryldiazenyl]- piperazines. Part I. Isomers of N-(2,3-Dimethylphenyl)-N’-(Aryldiazenyl)- Piperazines

Fan¹,

Vaughan²

2015

CHEM

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This paper describes the synthesis of several new series of 1-(2-aryldiazen-1-yl-) 4-arylpiperazines and 1-(2-aryldiazen-1-yl-)4-arylalkylpiperazines by using diazonium coupling between arenediazonium ions with the appropriate 1-arylpiperazine or the 1-arylalkylpiperazine. The new compounds have a common thread in that they are isomers of the series of N-(2,3-dimethylphenyl)-N'-(aryldiazenyl)-piperazines. The new triazenes have been characterized by IR and NMR spectroscopy and mass spectrometry.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of a Series of 1-Aryl-4-[aryldiazenyl]- piperazines. Part I. Isomers of N-(2,3-Dimethylphenyl)-N’-(Aryldiazenyl)- Piperazines

Fan¹,

Vaughan²

2015

CHEM

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“…4 The bis-triazenes of type 9 were characterized by a range of spectroscopic techniques, and the data was compared with some previously published work 5 in which several of the bis-aryldiazenyl-piperazines had already been described. Subsequently, we extended the study of bis-triazenes to the 1,4-di-[2-aryl-1-diazenyl]-2-methylpiperazines (10), which were prepared by diazonium coupling to 2-methylpiperazine, 6 and then to the 1,4-di-[2-aryl-1-diazenyl]-2,6-dimethylpiperazines (11).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of several series of 4-acyl-1-[2-aryl-1-diazenyl]piperazines

Renee

VaughanKeith²

2014

Can. J. Chem.

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Five series of a novel class of 4-acyl-1-[2-aryl-1-diazenyl]piperazines have been synthesized and characterized: the 4-acetyl-1-[2-aryl-1-diazenyl]piperazines [series 1]; the 4-cyclohexylcarbonyl-1-[2-aryl-1-diazenyl]piperazines [series 2]; the 4-benzoyl-1-[2-aryl-1-diazenyl]piperazines [series 3]; the benzyl 4-[2-aryl-1-diazenyl]-1-piperazinecarboxylates [series 4]; and the t-butyl 4-[2-aryl-1-diazenyl]-1-piperazinecarboxylates [series 5]. The compounds were synthesized by diazotization of a primary aromatic amine and subsequent coupling to an appropriate secondary amine: 1-acetylpiperazine [series 1]; 1-(cyclohexylcarbonyl)-piperaizine [series 2]; 1-benzoylpiperazine [series 3]; benzyl 1-piperazinecarboxylate [series 4]; and t-butyl piperazine-1-carboxylate (1-BOC-piperazine) [series 5]. The compounds of series 1-5 were characterized by 1 H NMR, 13 C NMR, high-resolution MS and IR spectroscopy. The model compounds 1,4-di[2-aryl-1-diazenyl]piperazines, and ethyl 4-[2-aryl-1-diazenyl]-1-piperazinecarboxylates were used to facilitate the assignment of the chemical shifts specific to the piperazine ring carbons. HSQC spectra of select compounds established the correlation between proton and carbon resonance signals. Résumé : Cinq séries d'une nouvelle classe de 4-acyl-1-[2-aryl-1-diazényl]pipérazines ont été synthétisées et caractérisées : les 4-acétyl-1-[2-aryl-1-diazényl]pipérazines [série 1], les 4-cyclohéxylcarbonyl-1-[2-aryl-1-diazényl]pipérazines [série 2], les 4-benzoyl-1-[2-aryl-1-diazényl]pipérazines [série 3], les benzyl 4-[2-aryl-1-diazényl]-1-pipérazinecarboxylates [série 4] et les t-butyl 4-[2-aryl-1-diazényl]-1-pipérazinecarboxylates [série 5]. Ces composés ont été synthétisés par diazotation d'une amine aromatique primaire suivie d'un couplage avec une amine secondaire appropriée : 1-acétylpipérazine [série 1], 1-(cyclohéxylcarbonyl)-pipérazine [série 2], 1-benzoylpipérazine [série 3], benzyl 1-pipérazinecarboxylate [série 4] et t-butyl pipérazine-1-carboxylate (1-BOCpipérazine) [série 5]. Les composés des séries 1 à 5 ont été caractérisés par RMN (résonance magnétique nucléaire) 1 H, RMN 13 C, spectrométrie de masse à haute résolution et spectroscopie IR. Les composés modèles 1,4-di[2-aryl-1-diazényl]pipérazines et éthyl 4-[2-aryl-1-diazényl]-1-pipérazinecarboxylates ont été utilisés pour faciliter l'attribution des déplacements chimiques spécifiques aux carbones du cycle de la pipérazine. Les spectres HSQC d'une sélection de composés ont permis d'établir une corrélation entre les signaux de résonance du proton et du carbone. [Traduit par la Rédaction]Mots-clés : triazène, pipérazine, acyl-1-[2-aryl-1-diazényl]pipérazines, diazotation, pipérazine-1-carboxylate, spectroscopie de réso-nance magnétique nucléaire, spectroscopie IR (infrarouge), spectrométrie de masse, équilibre dynamique.

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“…"The bis-triazenes of type 8 were characterized by a range of spectroscopic techniques and the data was compared with some previously published work [5] in which several of the bis-aryldiazenyl-piperazines had already been described." Subsequently, we extended the study of bis-triazenes to the 1,4-di-[2-aryl-1-diazenyl]-2-methylpiperazines (9), which were prepared by diazonium coupling to 2-methylpiperazine [6], and then to the 1,4-di-[2-aryl-1-diazenyl]-2,6-dimethylpiperazines (10) [7].…”

Section: R = -Me 2 R = -Et 3 R = -Ch 2 Ch 2 Oh 4 R = -Bu 5 R = -I-prmentioning

confidence: 99%

“…In this paper, we now report the formation of 24 new triazenes derived from 1-alkylpiperazines, namely the 1-ethyl series (2), the 1-hydroxyethyl series (3), the 1-butyl series (4) and the 1-iso-propyl series (5).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of New Compounds in the Series 1-alkyl-4- [2-aryl-1-diazenyl]piperazines

MacLeod¹,

Vaughan²

2015

TOOCJ

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24 New triazenes derived from the 1-alkylpiperazines have been synthesized. Each 1-alkylpiperazine was treated with a diazonium salt solution to produce the new triazenes, which have been characterized by proton and carbon-13 NMR spectroscopy, IR spectroscopy and by mass spectrometric analysis. Assignment of the chemical shifts to specific protons and carbons in the piperazine ring was facilitated by comparison with the chemical shifts in the previously reported 1-methyl-4-[2-aryl-1-diazenyl]piperazines (1).

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NEW N,N′-bis(SUBSTITUTED PHENYLAZO) PIPERAZINES AND THEIR CLEAVAGE REACTIONS IN ACETIC ACID

Cited by 19 publications

References 15 publications

Synthesis and Characterization of a Series of 1-Aryl-4-[aryldiazenyl]- piperazines. Part I. Isomers of N-(2,3-Dimethylphenyl)-N’-(Aryldiazenyl)- Piperazines

Synthesis and Characterization of a Series of 1-Aryl-4-[aryldiazenyl]- piperazines. Part I. Isomers of N-(2,3-Dimethylphenyl)-N’-(Aryldiazenyl)- Piperazines

Synthesis and characterization of several series of 4-acyl-1-[2-aryl-1-diazenyl]piperazines

Synthesis and Characterization of New Compounds in the Series 1-alkyl-4- [2-aryl-1-diazenyl]piperazines

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