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Synthesis of 1,2,3,4,5,6,7‐Heptasubstituted Cycloheptatrienes through Cycloaddition Reactions of Substituted Cyclopentadienones
Author(s) -
Platonov Dmitry N.,
Belyy Aleksandr Yu.,
Ananyev Ivan V.,
Tomilov Yury V.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600516
Subject(s) - chemistry , cycloaddition , ring (chemistry) , medicinal chemistry , cycloheptatriene , computational chemistry , organic chemistry , catalysis
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.