(n +3)-Cyclization for the Formation of Benzo[7]annulene Derivatives via a [1,4]-Hydride Shift: A Novel Cyclization Mode Involving an Internal Redox Reaction.

Autor: Nagaki, Jun, Kawasaki-Takasuka, Tomoko, Mori, Keiji
Předmět:
Zdroj: Synlett; Nov2024, Vol. 35 Issue 18, p2143-2147, 5p
Abstrakt: We report a unique synthetic route to benzo[7]annulene derivatives. When benzylidene malonates having a 1-(N , N -dialkylamino)alkyl group at the ortho -position are treated with a stoichiometric amount of M(OTf)3 (M = Sc, Yb, Gd), three transformations ([1,4]-hydride shift/isomerization into an enamine/intramolecular Stork enamine acylation) proceed sequentially to afford various benzo[7]annulene derivatives in moderate chemical yields. To our knowledge, the present reaction is the first example of an internal redox reaction involving a [1, n ]-hydride shift/(n +3)-cyclization process. [ABSTRACT FROM AUTHOR]
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