Ruthenium(II)-Catalyzed Migratory C–H Allylation/Hydroamination Cascade for the Synthesis of Rutaecarpine Analogues

Published as part of the Special Topic Ruthenium in Organic Synthesis

Abstract

An unprecedented allyl migration from a remote position of a quinazoline moiety through a ruthenium(II) shuttle is reported. This present cascade reaction is initiated through the formation of an η³-ruthenium–allyl complex followed by C–H allylation at the ortho position of the 2-aryl moiety. Finally, hydroamination with the quinazolinone -NH group, which is formed through tautomerization of the quinazoline, furnishes the annulation product. This exceedingly fast cascade reaction is complete within 10 minutes to provide rutaecarpine analogues in a single operation.

Key words

allyl migration - C–H activation - quinazolinones - ruthenium(II) catalysis - cascade reaction - rutaecarpine scaffold

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