Self-Condensation of Enaminodiones as a Method for Benzene Ring Construction: Synthesis of Diacyl-Substituted Phenols and Catechols

A novel transition metal-free approach for the construction of the benzene core has been developed through self-condensation of available enaminodiones. Functionalized acyl-substituted phenols and catechols were obtained in 29–97% yields with high chemoselectivity under mild conditions. This base-pr...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 84; no. 10; pp. 6491 - 6501
Main Authors Obydennov, Dmitrii L, Chernyshova, Elena V, Sosnovskikh, Vyacheslav Y
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.05.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
2-HYDROXYBENZOPHENONES
CYCLIZATIONS
BENZANNULATION REACTIONS
ANNULATION
DIVERSE
BIOLOGICAL-ACTIVITY
REGIOSELECTIVE SYNTHESIS
REACTIVITY
1,3-BIS-SILYL ENOL ETHERS
TRANSITION-METAL-FREE
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Summary:A novel transition metal-free approach for the construction of the benzene core has been developed through self-condensation of available enaminodiones. Functionalized acyl-substituted phenols and catechols were obtained in 29–97% yields with high chemoselectivity under mild conditions. This base-promoted formal [4+2] annulation proceeds via cyclohexanone formation and involves the cascade transformation based on double Michael addition and aromatization (retro-Claisen cleavage and amine elimination).
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b00623