Bismuth(III) Chloride Catalyzed Intramolecular Hetero-Diels–Alder Reaction: Access to cis-Fused Angular Hexahydrobenzo[c]acridines

Abstract

New polycyclic hexahydrobenzo[c]acridines were synthesized in excellent yields by intramolecular [4+2]-cycloaddition reactions of aldimines derived from aromatic amines and 2-(4-methylpent-3-en-1-yl)benzaldehyde in acetonitrile in the presence of 10 mol% of bismuth(III) chloride. The reaction is highly diastereoselective, giving cis-fused benzoacridine derivatives preferentially.

Key words

hetero-Diels–Alder reactions - catalysis - heterocycles - polycycles - aldimines - aldehydes

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