Synthesis 2017; 49(18): 4205-4212
DOI: 10.1055/s-0036-1588472
special topic
© Georg Thieme Verlag Stuttgart · New York

Iron-Catalyzed Intramolecular Alkyne–Carbonyl Metathesis: A New Cyclization Strategy for the Synthesis of Benzocarbazole and Azepino[1,2-a]indole Derivatives

Kartick Paul
Department of Chemistry, Jadavpur University, Kolkata 700 032, West Bengal, India   Email: jumasish2004@yahoo.co.in   Email: umasish@gmail.com
,
Swapnadeep Jalal
Department of Chemistry, Jadavpur University, Kolkata 700 032, West Bengal, India   Email: jumasish2004@yahoo.co.in   Email: umasish@gmail.com
,
Sandip Kundal
Department of Chemistry, Jadavpur University, Kolkata 700 032, West Bengal, India   Email: jumasish2004@yahoo.co.in   Email: umasish@gmail.com
,
Baitan Chakraborty
Department of Chemistry, Jadavpur University, Kolkata 700 032, West Bengal, India   Email: jumasish2004@yahoo.co.in   Email: umasish@gmail.com
,
Umasish Jana*
Department of Chemistry, Jadavpur University, Kolkata 700 032, West Bengal, India   Email: jumasish2004@yahoo.co.in   Email: umasish@gmail.com
› Author Affiliations
Further Information

Publication History

Received: 19 April 2017

Accepted after revision: 29 May 2017

Publication Date:
20 July 2017 (eFirst)

Published as part of the Special Topic Modern Cyclization Strategies in Synthesis

Abstract

An efficient synthesis of benzocarbazoles and benzo[3,4]azepino[1,2-a]indole derivatives through an FeCl3-catalyzed alkyne–aldehyde metathesis reaction is described. Structurally diverse benzo[a]carbazoles, benzo[c]carbazoles, and benzo[3,4]azepino[1,2-a]indoles have been achieved in good yields with high regio- and chemoselectivity in the presence of catalytic, inexpensive, and environmentally friendly FeCl as a catalyst.

Supporting Information

 
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