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Towards Isocoumarin‐Fused Enediyne Systems through the Electrophilic Cyclization of Methyl o ‐(Buta‐1,3‐diynyl)benzoates
Author(s) -
Danilkitalia A.,
Gurskaya Larisa Y.,
Vasilyev Aleksander V.,
Balova Irina A.
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.201501262
Subject(s) - isocoumarin , enediyne , chemistry , sonogashira coupling , electrophile , benzoates , isocoumarins , synthon , stereochemistry , electrophilic substitution , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , palladium
The synthesis of enediynes fused to an isocoumarin core was achieved through the electrophilic cyclization of o ‐(buta‐1,3‐diynyl)benzoates as a key step, followed by the Sonogashira coupling of the resulting 3‐ethynyl‐4‐iodoisocoumarins with acetylenes. This approach allowed different substituents to be introduced to both ethynyl moieties with complete regiocontrol. The ability of the isocoumarin‐fused enediynes to undergo Bergman cyclization was studied by differential scanning calorimetry.