A survey of synthetic routes towards 2-azaanthraquinones

Jacobs, Jan; Tehrani, Kourosch Abbaspour; Kimpe, Norbert De

doi:10.1016/j.tet.2011.10.017

Cited by 11 publications

(4 citation statements)

References 99 publications

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“…These oxidations of o-and p-dihydroxy derivatives to the corresponding quinones have been described by different authors. 22,23 According to these findings, the reaction pathway shown in Figure 7 is proposed for the phenylglycine methyl ester degradation in the presence of hydroquinone. In the presence of amino compounds and air, oand p-diphenols are able to produce the corresponding quinones to some extent.…”

Section: ■ Discussionmentioning

confidence: 92%

Contribution of Phenolic Compounds to Food Flavors: Strecker-Type Degradation of Amines and Amino Acids Produced by o- and p-Diphenols

Delgado

Zamora

Hidalgo

2015

J. Agric. Food Chem.

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The ability of 20 phenolic derivatives to produce the Strecker-type degradation of phenylalanine and phenylglycine methyl ester was studied to investigate both the direct degradation of amino acids and amines by phenolic compounds in the absence of added oxidants and the effect of the number and positions of hydroxyl groups in the aromatic ring of the phenolic compound in relation to its ability to produce carbonyl derivatives from amino compounds. The obtained results showed that polyphenols can produce the Strecker degradation of amino acids and amines in the absence of added oxidants. The only requisite for producing the reaction is the presence of two hydroxyl groups in ortho or para positions. However, the presence of two hydroxyl groups in meta position in an additional aromatic ring can inhibit the Strecker-degrading ability of the hydroxyl groups in ortho or para positions. A reaction pathway that explains all of these findings is proposed. In addition, the effect of reaction conditions on the obtained reaction yields was studied. Activation energies (Ea) for phenylacetaldehyde formation from phenylalanine in the presence of hydroquinone, 1,2,4-trihydroxybenzene, and benzoquinone were 32.9, 31.5, and 28.8 kJ/mol, respectively.

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Section: ■ Discussionmentioning

confidence: 92%

Contribution of Phenolic Compounds to Food Flavors: Strecker-Type Degradation of Amines and Amino Acids Produced by o- and p-Diphenols

Delgado

Zamora

Hidalgo

2015

J. Agric. Food Chem.

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“…The differences of electrophilicity of carbonyl and steric hindrance of intermediate B explained that the formation of benzo[ g ]quinoline‐5,10‐diones was highly regioselective. In addition, the stabilizing electron‐withdrawing group of benzo[ g ]quinoline‐5,10‐dione prevents the aromatization of it even under severe reaction condition, such as microwave or high reaction temperature, or high active oxidants such as peroxide .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Tetrahydrobenzo[g]Quinoline Derivatives Using Recoverable Carbonaceous Material as Heterogeneous Catalyst

Lin

Chen

et al. 2017

Journal of Heterocyclic Chem

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A variety of substituted benzo[g]quinoline‐5,10‐dione derivatives were synthesized via one‐pot three‐component reaction of 2‐hydroxynaphthalene‐1,4‐dione, aromatic aldehydes, and (E)‐3‐aminobut‐2‐enoates using carbonaceous material as the heterocyclic catalyst. This procedure is simple and efficient owing to short reaction times, easy work‐up, and recovery of heterogeneous catalyst. This procedure develops an efficient and promising synthetic method to construction of the benzo[g]quinoline‐5,10‐dione skeleton.

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“…A summary of the different synthetic routes towards 2-azaanthraquinones has already been reported, partially by our group, and shows that 5 can be synthesized by a myriad of methods. 10 It is however important to mention that classic methods for preparing isoquinolines do not necessarily prove to be the methods of choice for preparing the benzo[g]isoquinoline-5,10dione compounds. Since this report, no new methods towards the unfunctionalized benzo[g]isoquinoline-5,10-dione (5) have been published.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antitubercular activity of 1- and 3-substituted benzo[g]isoquinoline-5,10-diones

et al. 2019

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A survey of synthetic routes towards 2-azaanthraquinones

Cited by 11 publications

References 99 publications

Contribution of Phenolic Compounds to Food Flavors: Strecker-Type Degradation of Amines and Amino Acids Produced by o- and p-Diphenols

Contribution of Phenolic Compounds to Food Flavors: Strecker-Type Degradation of Amines and Amino Acids Produced by o- and p-Diphenols

Synthesis of Tetrahydrobenzo[g]Quinoline Derivatives Using Recoverable Carbonaceous Material as Heterogeneous Catalyst

Synthesis and antitubercular activity of 1- and 3-substituted benzo[g]isoquinoline-5,10-diones

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