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

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 e...

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Bibliographic Details
Published in:European journal of organic chemistry 2016-08, Vol.2016 (23), p.4105-4110
Main Authors: Platonov, Dmitry N., Belyy, Aleksandr Yu, Ananyev, Ivan V., Tomilov, Yury V.
Format: Article
Language:English
Subjects:
Cycloaddition
Diazo compounds
Domino reactions
Medium-ring compounds
Small ring systems
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Summary: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. Regioselective convergent three‐ to four‐step synthesis of heptasubstituted cycloheptatrienes with a wide range of substituents on the cycle was carried out, starting from 2‐oxo‐4,5‐diphenylcyclopenta‐3,5‐diene‐1,3‐dicarboxylate and 2,3‐dimethyl(2,3‐diphenyl)cycloprop‐2‐ene‐1‐carboxylates or 2‐diazo‐3‐(trifluoromethyl)butenoates.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201600516