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

Mohammad Saifuddin; Srinivas Samala; Deevi G. Venkata Krishna; Bijoy Kundu

doi:10.1055/s-0033-1338424

Synthesis, Table of Contents

Synthesis 2013; 45(11): 1553-1563
DOI: 10.1055/s-0033-1338424

paper

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

^aMedicinal 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

^aMedicinal 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

^bSophisticated Analytical and Instrumental Facility, CSIR-Central Drug Research Institute, Lucknow 226001, India

,

Bijoy Kundu*

^aMedicinal 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

^bSophisticated Analytical and Instrumental Facility, CSIR-Central Drug Research Institute, Lucknow 226001, India

^cAcademy of Scientific and Innovative Research, New Delhi, India

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Abstract

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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.

Key words

polyheterocycles - alkyne - indole - annulation - Lewis acid - regioselective

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References

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Supplementary Material

Supporting Information

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]

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]