Synthesis of 1,2,3,4,5,6,7-Heptasubstituted Cycloheptatrienes through Cycloaddition Reactions of Substituted Cyclopentadienones

Synthesis of 1,2,3,4,5,6,7-Heptasubstituted Cycloheptatrienes through Cycloaddition Reactions of Substituted Cyclopentadienones Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2016, Volume: 2016, Number: 23, Pages: 4105-4110 Pages count : 6 DOI: 10.1002/ejoc.201600516

Authors

Platonov Dmitry N. ¹ , Belyy Aleksandr Yu. ¹ , Ananyev Ivan V. ² , Tomilov Yury V. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov st., 119991 Moscow, Russian Federation

Two schemes for synthesizing heptasubstituted cycloheptatrienes with various substituents in the ring are suggested. The first method is based on cycloaddition of 2,5-dimethoxycarbonyl-3,4-diphenylcyclopentadienone with substituted cyclopropenes and allows cycloheptatrienes containing two or three electron-withdrawing substituents in the molecule to be obtained. The second method employs a cascade reaction between a substituted cyclopentadienone and appropriate vinyldiazoacetates. It allows the number of electron-withdrawing substituents to be increased to five. In all cases, heptasubstituted cycloheptatrienes are formed as just one of the possible isomers.

Platonov D.N. , Belyy A.Y. , Ananyev I.V. , Tomilov Y.V.
Synthesis of 1,2,3,4,5,6,7-Heptasubstituted Cycloheptatrienes through Cycloaddition Reactions of Substituted Cyclopentadienones
European Journal of Organic Chemistry. 2016. V.2016. N23. P.4105-4110. DOI: 10.1002/ejoc.201600516 WOS Scopus OpenAlex

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