Use of β,γ‐Unsaturated α‐Ketocarbonyls for a Totally Regioselective Oxidative Multicomponent Synthesis of Polyfunctionalized Pyridines

Allais, Christophe; Constantieux, Thierry; Rodríguez, Jean

doi:10.1002/chem.200902491

Cited by 62 publications

(14 citation statements)

References 62 publications

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“…However, our process was very clean, and no by‐products of this type could be detected. Thus, in agreement with Rodriguez et al,24 we presume that atmospheric oxygen could be responsible for the oxidation step leading to aromatisation.…”

Section: Resultssupporting

confidence: 93%

A General Synthesis of Bis‐α‐acyloxy‐1,4‐ and ‐1,5‐diketones Through Catalytic Oxidative Opening of Acylated THF and THP Diols

Piccialli¹,

D’Errico²,

Borbone³

et al. 2013

Eur J Org Chem

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The first general synthesis of bis‐α‐acyloxy‐1,4‐ and ‐1,5‐diketones has been accomplished in a catalytic oxidative opening of bis‐acylated THF and THP (tetrahydropyran) diols, which were synthesised by osmium‐ or ruthenium‐catalysed oxidative cyclisation of 1,5‐ and 1,6‐dienes. The overall sequence corresponds to the regioselective double ketoacyloxylation of the starting diene. The synthesised bis‐α‐acyloxy‐1,5‐dicarbonyl compounds have been transformed into pyridine‐based oxido pincer ligands or pyrazinedimethanol substances, leading to the discovery of unprecedented aromatisation routes.

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Section: Resultssupporting

confidence: 93%

A General Synthesis of Bis‐α‐acyloxy‐1,4‐ and ‐1,5‐diketones Through Catalytic Oxidative Opening of Acylated THF and THP Diols

Piccialli¹,

D’Errico²,

Borbone³

et al. 2013

Eur J Org Chem

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“…An oxidative domino three-component reaction of α-ketophosphonates 290 , ammonium acetate and various 1,3-dicarbonyl compounds 289 to give pyridinylphosphonates 291 has been described. This method allowed the synthesis of highly functionalized pyridinylphosphonates 291 in 63–80% yields in refluxing AcOH/toluene 4:1 in the presence of 4 Å molecular sieves ( Scheme 59 ) [ 97 ].…”

Section: Reviewmentioning

confidence: 99%

Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

Haji¹

2016

Beilstein J. Org. Chem.

149

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SummaryMulticomponent reactions (MCRs) are one of the most important processes for the preparation of highly functionalized organic compounds in modern synthetic chemistry. As shown in this review, they play an important role in organophosphorus chemistry where phosphorus reagents are used as substrates for the synthesis of a wide range of phosphorylated heterocycles. In this article, an overview about multicomponent reactions used for the synthesis of heterocyclic compounds bearing a phosphonate group on the ring is given.

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“…[43] Following Michael addition and ring closure, autoxidation provides pyridines with methyl, aryl, carbonyl, and phosphonate groups. Significantly, the use of a-ketocarbonyl Michael acceptors prevented reversible addition, and provided access to 4-substituted pyridines.…”

Section: Brandsma Et Al Developed a Newmentioning

confidence: 99%

“…The [3 + 2 + 1] synthesis of tetrasubstituted pyridines. [43] Scheme 32. The [3 + 2 + 1] three-step synthesis of pyridine and pyridinium chloride derivatives.…”

Section: Brandsma Et Al Developed a Newmentioning

confidence: 99%

Recent Strategies for the Synthesis of Pyridine Derivatives

Hill

2010

Chemistry A European J

468

130

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Recent advances in pyridine synthesis are described. Modification of traditional condensation strategies continues to be a recurrent theme in contemporary literature. Advancements in transition-metal-catalyzed cyclization and cross-coupling procedures offer new routes to functionalized pyridine derivatives. These recently developed methodologies are a valuable addition to azaheterocycle synthesis.

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Use of β,γ‐Unsaturated α‐Ketocarbonyls for a Totally Regioselective Oxidative Multicomponent Synthesis of Polyfunctionalized Pyridines

Cited by 62 publications

References 62 publications

A General Synthesis of Bis‐α‐acyloxy‐1,4‐ and ‐1,5‐diketones Through Catalytic Oxidative Opening of Acylated THF and THP Diols

A General Synthesis of Bis‐α‐acyloxy‐1,4‐ and ‐1,5‐diketones Through Catalytic Oxidative Opening of Acylated THF and THP Diols

Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

Recent Strategies for the Synthesis of Pyridine Derivatives

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