Oxofunctionalized<i>Trans</i>-2-carboxycinnamic Acids by Catalytic Domino Oxidation of Naphthols and Hydronaphthoquinones

Giurg, Mirosław; Muchalski, Hubert; Kowal, Ewa

doi:10.1080/00397911.2011.561945

Cited by 6 publications

(1 citation statement)

References 37 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Similar ring-degradation took place, when substituted naphthalenes were oxidized. Cinnamic acid or benzofurane derivatives were the final products [160,161].…”

Section: Organoselenium Compounds As Oxidizing Agents and Oxidatiomentioning

confidence: 99%

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

2015

View full text Add to dashboard Cite

A variety of selenium compounds were proven to be useful reagents and catalysts for organic synthesis over the past several decades. The most interesting aspect, which emerged in recent years, concerns application of hydroperoxide/selenium(IV) oxide and hydroperoxide/organoselenium catalyst systems, as "green reagents" for the oxidation of different organic functional groups. The topic of oxidations catalyzed by organoselenium derivatives has rapidly expanded in the last fifteen years This paper is devoted to the synthetic applications of the oxidation reactions mediated by selenium compounds such as selenium(IV) oxide, areneseleninic acids, their anhydrides, selenides, diselenides, benzisoselenazol-3(2H)-ones and other less often used other organoselenium compounds. All these compounds have been successfully applied for various oxidations useful in practical organic syntheses such as epoxidation, 1,2-dihydroxylation, and α-oxyfunctionalization of alkenes, as well as for ring contraction of cycloalkanones, conversion of halomethyl, hydroxymethyl or active methylene groups into formyl groups, oxidation of carbonyl compounds into carboxylic acids and/or lactones, sulfides into sulfoxides, and secondary amines into nitrones and regeneration of parent carbonyl compounds from their azomethine derivatives. Other reactions such as dehydrogenation and aromatization, active carbon-carbon bond cleavage, oxidative amidation, bromolactonization and oxidation of bromide for subsequent reactions with alkenes are also successfully mediated by selenium (IV) oxide or organoselenium compounds. The oxidation mechanisms of ionic or free radical character depending on the substrate and oxidant are discussed. Coverage of the literature up to early OPEN ACCESSMolecules 2015, 20 10206 2015 is provided. Links have been made to reviews that summarize earlier literature and to the methods of preparation of organoselenium reagents and catalysts.

show abstract

“…Similar ring-degradation took place, when substituted naphthalenes were oxidized. Cinnamic acid or benzofurane derivatives were the final products [160,161].…”

Section: Organoselenium Compounds As Oxidizing Agents and Oxidatiomentioning

confidence: 99%

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

2015

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: Oxofunctionalized trans‐2‐Carboxycinnamic Acids by Catalytic Domino Oxidation of Naphthols and Hydronaphthoquinones.

2012

View full text Add to dashboard Cite

show abstract

Study of the Oxidative Cleavage Proposed in the Biogenesis of Transtaganolides/Basiliolides: Pyran‐2‐one Aromaticity‐Mediated Regioselective Control and Biogenetic Implications

2020

View full text Add to dashboard Cite

The synthetic feasibility of the oxidative cleavage: epoxidation of 7‐O‐geranylscopoletin followed by electrocyclic ring‐opening, proposed in the biogenesis of transtaganolides/basiliolides is studied. Unlike the proposed pericyclic reactions, this pathway has not yet been addressed. Three synthetic strategies have been tested consisting of: i) Baeyer–Villiger oxidation of p‐quinoids, ii) hydrolysis of quinone monoketals, or iii) direct fragmentation by using oxygen donors. Oxidation of the benzene ring of hydroxylated coumarins has been achieved using peroxyacids, but cleavage took place between undesired positions. The aromaticity conservation of the pyran‐2‐one cycle during oxidation is the controlling factor of these observed regioselectivities. The use of a 4,5‐dihydroxy‐2‐methoxycinnamate model, in which the pyran‐2‐one ring does not exert influence on oxidation, has allowed the design of a synthetic sequence toward an analogue of the natural pyran‐2‐one isolated from Thapsia transtagana, key in the biogenesis. Mechanistic proposals for the obtained results as well as their biogenetic implications are raised.

show abstract

OxofunctionalizedTrans-2-carboxycinnamic Acids by Catalytic Domino Oxidation of Naphthols and Hydronaphthoquinones

Cited by 6 publications

References 37 publications

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

ChemInform Abstract: Oxofunctionalized trans‐2‐Carboxycinnamic Acids by Catalytic Domino Oxidation of Naphthols and Hydronaphthoquinones.

Study of the Oxidative Cleavage Proposed in the Biogenesis of Transtaganolides/Basiliolides: Pyran‐2‐one Aromaticity‐Mediated Regioselective Control and Biogenetic Implications

Contact Info

Product

Resources

About