Synthesis 2019; 51(12): 2523-2531
DOI: 10.1055/s-0037-1611525
special topic
© Georg Thieme Verlag Stuttgart · New York

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

Gurupada Bairy
a  Organic 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
b  Academy of Scientific and Innovative Research (AcSIR), Jadavpur, Kolkata 700032, West Bengal, India
,
Arijit Nandi
a  Organic 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
a  Organic 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
b  Academy of Scientific and Innovative Research (AcSIR), Jadavpur, Kolkata 700032, West Bengal, India
,
Ranjan Jana*
a  Organic 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
b  Academy of Scientific and Innovative Research (AcSIR), Jadavpur, Kolkata 700032, West Bengal, India
› Author Affiliations
This work was financially supported by the Department of Science and Technology (DST), Science and Engineering Research Board (SERB), Government of India (Ramanujan Fellowship Award No. SR/S2/RJN-97/2012, Extra Mural Research Grant No. EMR/2014/000469). G.B. thanks UGC and K.M. thanks CSIR for their fellowships.
Further Information

Publication History

Received: 11 March 2019

Accepted after revision: 27 March 2019

Publication Date:
26 April 2019 (online)

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.

Supporting Information

 
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