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Synlett 2019; 30(18): 2081-2085
DOI: 10.1055/s-0039-1690700
letter
© Georg Thieme Verlag Stuttgart · New York

A General Synthesis of Benzoazepinoindoles – A New Class of Heterocycles

Jeremy C. Dobrowolski
a   School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia
,
Duyen H.T. Nguyen
a   School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia
,
Benjamin H. Fraser
b   The Australian Nuclear Science and Technology Organisation, Kirrawee DC, NSW 2232, Australia
,
Mohan Bhadbhade
c   Solid State & Elemental Analysis Unit, Mark Wainwright Analytical Centre, Division of Research, The University of New South Wales, Sydney, NSW 2052, Australia   Email: n.kumar@unsw.edu.au
,
David StC. Black
a   School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia
,
Naresh Kumar∗
a   School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia
› Author AffiliationsJ.C.D. thanks University of New South Wales (UNSW) for an Australian Postgraduate Award (APA) and Australian Institute for Nuclear Science and Engineering (AINSE) for a Residential Student Scholarship (RSS). We thank the Australian Research Council (ARC, Grant Number DP180100845) for funding.
Further Information

Publication History

Received: 14 August 2019

Accepted after revision: 18 September 2019

Publication Date:
09 October 2019 (online)

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Abstract

A new class of heterocyclic compounds, namely the benzoazepinoindolones, has been synthesised through a base-catalysed cyclisation reaction of 1,4-bis(2-aminophenyl)-2-phenylbutane-1,4-dione derivatives and features the prominent seven-membered azepine ring moiety. This synthesis has considerable scope for the rapid generation of more complex structures and is inexpensive and generally applicable.

Key words

dihydrobenzo[6,7]azepino[3,2-c]indolones - fused-ring systems - umpolung - condensation - heterocycles

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690700.
  • Supporting Information
 

  • References and Notes

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