Formation of Symmetric Azo-compounds from Primary Aromatic Amines by Lead Tetraacetate

Baer, Erich; Tosoni, Anthony L.

doi:10.1021/ja01593a061

Cited by 57 publications

(18 citation statements)

References 3 publications

(3 reference statements)

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“…6 Various synthetic methods 7 have been developed including oxidation of hydrazines, 8 reduction of azoxybenzenes, 9 coupling of aryl diazonium salts with nucleophiles, 10 coupling of primary anilines with aromatic nitroso compounds, 11 and reductive coupling of nitroaromatics. 12 Azo compounds can also be obtained by oxidative coupling of anilines using stoichiometric oxidants, such as mercury(II) oxide, 13 manganese salts, 14 lead tetraacetate, 15 ferrate salts, 16 and tert -butyl hypoiodite. 17 Metal-catalyzed oxidative coupling of anilines using O 2 has also been reported.…”

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confidence: 99%

Facile Cu(I)-Catalyzed Oxidative Coupling of Anilines to Azo Compounds and Hydrazines with Diaziridinone under Mild Conditions

Zhu

Shi

2013

Org. Lett.

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A mild and highly efficient Cu(I)-catalyzed oxidative coupling of anilines is described. Various primary and secondary anilines can be efficiently coupled under mild conditions to the corresponding azo compounds and hydrazines in high yields. This method provides a direct and practical access to these compounds, and is also amenable to gram scale with no special precautions to exclude air or moisture.

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confidence: 99%

Facile Cu(I)-Catalyzed Oxidative Coupling of Anilines to Azo Compounds and Hydrazines with Diaziridinone under Mild Conditions

Zhu

Shi

2013

Org. Lett.

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“…Of the myriad of synthetic methods for aromatic azo compounds,5 conventional methods for symmetric aromatic azo compounds involve reductive homodimerization of nitroarenes6 and oxidation of aromatic amines 5. 7 Nevertheless, these methods suffer from the stoichiometric use of environmentally unfriendly transition‐metal oxidants (e.g., Mn,7a Pb,7b and Hg7c,d salts), or from difficulty in controlling product distribution (e.g., the azo‐/azoxybenzene ratio in the reductive methods). In addition to these problems, great challenges remain in the synthesis of unsymmetric aromatic azobenzenes.…”

Section: Methodsmentioning

confidence: 99%

Oxidative Dimerization of Aromatic Amines using tBuOI: Entry to Unsymmetric Aromatic Azo Compounds

2012

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“…the melting points reported are uncorrected; the TAFF-supported metallic nitrates were prepared after Laszlo's procedure (8); the corresponding substrates were obtained by previously reported methods (11).…”

Section: Methodsmentioning

confidence: 99%

A Comparative Study of the Oxidation of Hantzsch Esters Induced by Taff-Metaluc Nitrates

Miranda¹,

Aceves²,

Gutiérrez³

et al. 1997

Heterocyclic Communications

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Several 4-(substituted) -Hantzsch esters upon oxidation with bentonite supported metallic nitrates (Ag + , Fe +3 , Cu +2 , Co +2 ) under mild conditions, afforded the corresponding pyridines. As result of a comparative study, a synergism between the nitrate and the metallic ions with the TAFF support is suggested. INTRODUCTION.Several 4-(substituted)-Hantzsch esters have been studied in great detail as cardiovascular drugs (1-3), also several Hantzsch pyridines are useful as antihypoxies (4,5), others exhibit acricidal, insecticidal, bactericidal and herbicidal activities (6).As it is well known, the Hantzsch synthesis is a widely used general procedure to obtain considerable structural modifications of pyridine; in this method the intermediate (1,4-dihydropyridine) is commonly aromatized by a set of different ways of oxidation. Several methods are available for the oxidative aromatization (7, 8); however most of them employ rather severe conditions.

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Formation of Symmetric Azo-compounds from Primary Aromatic Amines by Lead Tetraacetate

Cited by 57 publications

References 3 publications

Facile Cu(I)-Catalyzed Oxidative Coupling of Anilines to Azo Compounds and Hydrazines with Diaziridinone under Mild Conditions

Facile Cu(I)-Catalyzed Oxidative Coupling of Anilines to Azo Compounds and Hydrazines with Diaziridinone under Mild Conditions

Oxidative Dimerization of Aromatic Amines using tBuOI: Entry to Unsymmetric Aromatic Azo Compounds

A Comparative Study of the Oxidation of Hantzsch Esters Induced by Taff-Metaluc Nitrates

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