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

Gurupada Bairy; Arijit Nandi; Kartic Manna; Ranjan Jana

doi:10.1055/s-0037-1611525

Synthesis, Inhaltsverzeichnis

Synthesis 2019; 51(12): 2523-2531
DOI: 10.1055/s-0037-1611525

special topic

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

Gurupada Bairy

^aOrganic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, West Bengal, India eMail: rjana@iicb.res.in

^bAcademy of Scientific and Innovative Research (AcSIR), Jadavpur, Kolkata 700032, West Bengal, India

,

Arijit Nandi

^aOrganic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, West Bengal, India eMail: rjana@iicb.res.in

,

Kartic Manna

^aOrganic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, West Bengal, India eMail: rjana@iicb.res.in

^bAcademy of Scientific and Innovative Research (AcSIR), Jadavpur, Kolkata 700032, West Bengal, India

,

Ranjan Jana*

^aOrganic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, West Bengal, India eMail: rjana@iicb.res.in

^bAcademy of Scientific and Innovative Research (AcSIR), Jadavpur, Kolkata 700032, West Bengal, India

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Abstract

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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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Referenzen

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