γ-Carbonyl Quinones: Radical Strategy for the Synthesis of Evelynin and Its Analogues by C–H Activation of Quinones Using Cyclopropanols

Ilangovan, Andivelu; Saravanakumar, S. S.; Malayappasamy, Subramani

doi:10.1021/ol402229m

Cited by 125 publications

(31 citation statements)

References 24 publications

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“…The yields are good to excellent and mild conditions are coupled with short reaction times (127). Two methods of introducing the trifluoromethyl group to 1,4-benzo and 1,4-naphthoquinones offer reasonable to good yields under mild conditions.…”

Section: ð36þmentioning

confidence: 99%

Quinones

Finley

2016

Kirk-Othmer Encyclopedia of Chemical Technology

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Quinones, possessing two α,β‐unsaturated carbonyl groups usually in a six‐carbon atom ring, represent a unique structural unit. Their centrality in the synthesis of such important commercial substances as dyes and pharmaceuticals has resulted in extensive studies. In living matter, they are ubiquitous and vital to human metabolism. Quinones are of special interest to biochemists and to both synthetic and theoretical organic chemists. The types of reactions most often reported are nucleophilic addition, photochemistry, cycloaddition, electrophilic addition, radical alkylation, electrochemical, oxidation, and nucleophilic substitution. The synthesis of quinones is usually accomplished through oxidation of phenols or anilines.

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Section: ð36þmentioning

confidence: 99%

Quinones

Finley

2016

Kirk-Othmer Encyclopedia of Chemical Technology

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“…Another important silver catalyzed direct alkylation of quinones was the γ ‐carbonylation of quinones with cyclopropanols. In 2013, Ilangovan and co‐workers found that β ‐keto radicals 19 , which were generated from the oxidation ring opening of cyclopropanols 18 , could be added to quinones to furnish γ ‐carbonyl quinones (Scheme ) . With the assistance of AgNO 3 /K 2 S 2 O 8 oxidant system, cytotoxic natural products, such as 4,6‐dimethoxy‐2,5‐quinodihydrochalcone, evelynin and a series of other highly substituted γ ‐carbonyl quinones could be prepared in 32–80 % yields.…”

Section: Alkylation Of Quinonesmentioning

confidence: 99%

Recent Advances in Direct Functionalization of Quinones

2019

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Developing methods for the direct functionalization of quinones for assembly of highly functionalized quinones or bioactive natural products is an essential topic in the field of direct C–H functionalization. Quinone units are key motifs in many bioactive compounds and materials, and many innovative methods have been elaborated for the generation of these units. A major part of the established synthetic strategies combines installation of substituents on hydroquinones, phenols, or phenyl ethers through different coupling reactions with oxidation to produce the desired quinones. Most of these above‐mentioned methods introduce multiple chemical steps; however, the synthesis of quinoid compounds through the direct C–H functionalization of simple quinones remains challenging. This minireview summarizes the recently developed achievements for assembly of functionalized quinones through direct functionalization of simple quinones. Our focus will be on the methods and mechanism of these reactions that have appeared in the last two decades.

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“…Quinones play an important role in organic chemistry because of their unique structure. In 2013, Malayappasamy and co-workers reported an efficient and convenient method for the synthesis of γ-carbonyl quinones 95 via ring-opening and functionalization of cyclopropanols 91 with quinones 94 (Scheme 21) [99]. In this transformation, both AgNO 3 and FeSO 4 were all efficient catalysts for the ring-opening and functionalization reaction.…”

Section: Reviewmentioning

confidence: 99%

Oxidative radical ring-opening/cyclization of cyclopropane derivatives

Liu

Wang

Chen

et al. 2019

Beilstein J. Org. Chem.

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The ring-opening/cyclization of cyclopropane derivatives has drawn great attention in the past several decades. In this review, recent efforts in the development of oxidative radical ring-opening/cyclization of cyclopropane derivatives, including methylenecyclopropanes, cyclopropyl olefins and cyclopropanols, are described. We hope this review will be of sufficient interest for the scientific community to further advance the application of oxidative radical strategies in the ring-opening/cyclization of cyclopropane derivatives.

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γ-Carbonyl Quinones: Radical Strategy for the Synthesis of Evelynin and Its Analogues by C–H Activation of Quinones Using Cyclopropanols

Cited by 125 publications

References 24 publications

Quinones

Quinones

Recent Advances in Direct Functionalization of Quinones

Oxidative radical ring-opening/cyclization of cyclopropane derivatives

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