ChemInform Abstract: ULLMANN REACTIONS OF O‐(ACYLAMINO)ARYL HALIDES

Kalk, W.; Bien, Hans‐Samuel; Schuendehuette, K.-H.

doi:10.1002/chin.197722180

Chemischer Informationsdienst

1977

DOI: 10.1002/chin.197722180

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ChemInform Abstract: ULLMANN REACTIONS OF O‐(ACYLAMINO)ARYL HALIDES

W. Kalk¹,

Hans‐Samuel Bien²,

K.-H. Schuendehuette³

Abstract: Die Titelverbindun‐ gen (I) bzw. (IV) können ohne Aktivierung durch Elektronenakzeptor‐Substituenten mit metallischem Cu unter milden Bedingungen zu symm. Biarylverbindungen (II) bzw. (V) kondensiert werden (die Verbindungen (III) werden analog dargestellt).

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“…It would, of course, be desirable to incorporate some useful properties of benzo[c]cinnoline and its derivatives directing their use as dyes 21 , fiber intermediates 22 , charge-generating agents in electrophographic photoreceptors 23 and electrochromic polymers 24 into an azo dye. Such an attempt could also impart to the azo dye, some other characteristics of the benzo[c]cinnoline moiety as mutagenicity 25 and herbicidial/pesticidal activity 26 .…”

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Synthesis and electroreduction of 2-[(8-hydroxyquinoline-5-yl)azo]benzo[c]cinnoline in DMSO–H2O (1:1) medium

Öztürk

Durmuș

Uçkan

et al. 2010

Collect. Czech. Chem. Commun.

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2-[(8-Hydroxyquinoline-5-yl)azo]benzo[c]cinnoline (HQAB) was prepared and characterized by elemental analysis, MS, FTIR and 1 H NMR techniques. The electrochemical reduction of HQAB has been investigated by cyclic voltammetry, chronoamperometry and controlled potential electrolysis at mercury pool electrode in the pH range 3.5-9.4. The number of electrons transferred in the electrode reaction, diffusion coefficients and standart rate constants were calculated. In acidic medium, cyclic voltammograms display four cathodic peaks, with the total exchange of 6 e -and 6 H + . By contrast, the reverse scan displays two anodic peaks. Constant potential electrolysis at -1.0 V and TLC analysis of the product reveals that the reduction of azo group (in the bridge) in HQAB does not stop at the hydrazo stage but goes further through the cleavage of -NH-NH-linkage to give amino compounds as the final products. The voltammograms recorded in basic medium exhibit two cathodic peaks corresponding to 4 e -, 4 H + and two reverse anodic peaks, and thus the reduction stopped at hydrazo stage. A tentative mechanism for the reduction has been suggested.Azo dyes are perhaps, among the most extensively studied classes of organic compounds both from theoretical and practical viewpoints. The major reason for this is that their widespread use as chromophoric and metallochromic reagents 1-3 , colorants 4-8 , non-linear optic materials 9-12 , photosensitizers 13-15 and metal sensors [16][17][18] . An azo dye bearing the 8-hydroxyquinoline and benzo[c]cinnoline moieties would be expected to display, apart from the general characteristics of the azodyes, behaviors reminiscent to both compounds. Azo dyes attached to 8-hydroxyquinoline

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mentioning

confidence: 99%

Synthesis and electroreduction of 2-[(8-hydroxyquinoline-5-yl)azo]benzo[c]cinnoline in DMSO–H2O (1:1) medium

Öztürk

Durmuș

Uçkan

et al. 2010

Collect. Czech. Chem. Commun.

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ChemInform Abstract: ULLMANN REACTIONS OF O‐(ACYLAMINO)ARYL HALIDES

Abstract: Die Titelverbindun‐ gen (I) bzw. (IV) können ohne Aktivierung durch Elektronenakzeptor‐Substituenten mit metallischem Cu unter milden Bedingungen zu symm. Biarylverbindungen (II) bzw. (V) kondensiert werden (die Verbindungen (III) werden analog dargestellt).

Cited by 1 publication

References 1 publication

Synthesis and electroreduction of 2-[(8-hydroxyquinoline-5-yl)azo]benzo[c]cinnoline in DMSO–H2O (1:1) medium

Synthesis and electroreduction of 2-[(8-hydroxyquinoline-5-yl)azo]benzo[c]cinnoline in DMSO–H2O (1:1) medium

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