Synthesis 2019; 51(09): 1989-1994
DOI: 10.1055/s-0037-1612280
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of a Variety of Activated Pyrrolo[3,2,1-ij]quinolines

Jumina Jumina
a  Department of Chemistry, Faculty of Mathematics and Natural Science, Universitas Gadjah Mada, Yogyakarta, Indonesia
,
Daniel S. Wenholz
b  School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia   Email: d.black@unsw.edu.au
,
Naresh Kumar
b  School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia   Email: d.black@unsw.edu.au
,
David StC. Black*
b  School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia   Email: d.black@unsw.edu.au
› Author Affiliations
Financial support from the Australian Research Council is gratefully acknowledged (DP180100845).
Further Information

Publication History

Received: 12 November 2018

Accepted after revision: 26 January 2019

Publication Date:
28 February 2019 (eFirst)

Abstract

A range of 7,9-dimethoxypyrrolo[3,2.1-ij]quinolines have been prepared by the cyclisation of 7-formyl-1-diethylcarbethoxyindoles. The functionality at C5 has been varied by the conversion of the carbethoxy group into carboxy, azidocarbonyl and isocyanate groups. The hydroboration of a previously reported pyrroloquinolone gave a related 5-hydroxypyrrolo[3,2,1-ij]quinolone, and the hydroxyl group was sequentially converted into tosylate, azido and amino groups.

Supporting Information

 
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