Synthesis 2013; 45(11): 1553-1563
DOI: 10.1055/s-0033-1338424
paper
© Georg Thieme Verlag Stuttgart · New York

A Sequential One-Pot Protocol for the Synthesis of Dihydrobenzo[6,7]indolo-[3′,4′:3,4,5]azepino[2,1-a]isoquinolines Using a Gold–Silver Combined Catalyst[1]

Mohammad Saifuddin
a   Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226001, India   Fax: +91(522)2623405   eMail: bijoy_kundu@yahoo.com   eMail: b_kundu@cdri.res.in
,
Srinivas Samala
a   Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226001, India   Fax: +91(522)2623405   eMail: bijoy_kundu@yahoo.com   eMail: b_kundu@cdri.res.in
,
Deevi G. Venkata Krishna
b   Sophisticated Analytical and Instrumental Facility, CSIR-Central Drug Research Institute, Lucknow 226001, India
,
Bijoy Kundu*
a   Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226001, India   Fax: +91(522)2623405   eMail: bijoy_kundu@yahoo.com   eMail: b_kundu@cdri.res.in
b   Sophisticated Analytical and Instrumental Facility, CSIR-Central Drug Research Institute, Lucknow 226001, India
c   Academy of Scientific and Innovative Research, New Delhi, India
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Publikationsverlauf

Received: 12. März 2013

Accepted after revision: 26. März 2013

Publikationsdatum:
08. Mai 2013 (online)


Abstract

A sequential one-pot protocol for the synthesis of indole-based peri-annulated polyheterocycles using trifluoroacetic acid and a gold–silver combined catalyst system is described. The reaction is thought to proceed via an imine formation–cationic π-cyclization–alkyne activation–intramolecular hydroamination sequence to yield novel dihydrobenzo[6,7]indolo[3′,4′:3,4,5]azepino[2,1-a]isoquinolines in good yields.

Supporting Information