Preparation of 3‐hydroxy‐ and 3‐methoxy‐<i>N</i>‐heteroaryl‐2‐methyl‐4‐pyridones

Jakopcic, K.; Mintas, Mladen; Isufi, Islam

doi:10.1002/jhet.5570300225

Cited by 7 publications

(1 citation statement)

References 15 publications

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“…Such protection avoids the generation of an α-hydroxy ketone intermediate (Scheme ), accumulation of which will increase the rate of intermolecular reaction, leading to polymer formation. The 3-hydroxyl function can be protected by the formation of a methyl ether or more commonly a benzyl ether. ,, The methoxy group is typically cleaved by treatment with BBr 3 , whereas the benzyl group can be cleaved under more mild conditions, for instance, with BCl 3 , catalytic hydrogenation, or neat trifluoroacetic acid. This synthetic procedure has been reported in many patents. ,− …”

Section: Synthesis Of Hydroxypyridinonesmentioning

confidence: 99%

Hydroxypyridinone Journey into Metal Chelation

et al. 2018

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Hydroxypyridinones (HOPOs) form outstanding building blocks for the development of a variety of agents in the field of metal chelation. The pyridinone ring is easily synthesized and readily converted into tetradentate, hexadentate, and octadentate chelators. There is considerable potential for the control of the stereochemistry of the resulting metal complex and hence the properties of these multidentate molecules. Their ability to rapidly bind hard metals in aqueous media has facilitated the development of efficient applications in both biological and medical contexts. In this Review, an in-depth analysis of the synthetic methodologies for HOPO-based ligands is presented, as well as the many aspects to achieve optimal biological activity. Recent advances and current challenges for the future application of HOPO structures are outlined. The present flourishing development of drug candidates and diagnostic agents based on this chemical scaffold opens access to many new applications in analytical, environmental, and clinical science.

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Section: Synthesis Of Hydroxypyridinonesmentioning

confidence: 99%

Hydroxypyridinone Journey into Metal Chelation

et al. 2018

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Synthesis of N‐substituted 3‐hydroxy‐2‐methyl‐4‐pyridones and ‐pyridonimines

Farber

Osiander

Severin

1994

Journal of Heterocyclic Chem

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Carbohydrates with 1,4 glycosidic bonds like maltose, lactose, dextrin or starch react with primary amines as well as amino acids or proteins to give i.e. 3‐hydroxy‐2‐methyl‐4‐pyridones 5 and 3‐hydroxy‐2‐methyl‐4‐pyridonimines 7. A generally applicable synthesis of compounds of this type is described. The pyridones 5 and pyridonimines 7 are strongly complexing agents. Molybdenum‐derivatives, for instance, are suitable as fairly stable oxidation catalysts.

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