Synlett 2023; 34(20): 2433-2438
DOI: 10.1055/a-2103-9629
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Special Issue Dedicated to Prof. Hisashi Yamamoto

Synthesis of Furo- and Thienoquinolines by Using an Amine Oxidase-Inspired Catalyst

Pradip Ramdas Thorve
,
Biplab Maji  ∗
The authors thank SERB (CRG/2019/001232) and Indian Institute of Science Education and Research Kolkata (ARF) for financial support. P.R.T. thanks University Grants Commission for a fellowship.
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Dedicated to Professor Dr. Hisashi Yamamoto on the occasion of his 80th birthday

Abstract

We report the regioselective synthesis of furo- and thienoquinolines by using an amine oxidase-inspired catalyst (1,10-phenanthroline-5,6-dione) and an abundant Lewis acid (FeCl3) as a co-catalyst. The aerobic amine dehydrogenation proceeds under mild conditions and produces the quinolines in high yields. Mechanistic studies helped to identify the possible reaction intermediates and the specific role of the catalyst in the multistep cascade.

Key words

biomimetic catalyst - iron catalysis - aerobic oxidation - dehydrogenation - quinolines

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2103-9629.
  • Supporting Information


Publication History

Received: 30 April 2023

Accepted after revision: 31 May 2023

Accepted Manuscript online:
31 May 2023

Article published online:
19 July 2023

© 2023. Thieme. All rights reserved

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  • References and Notes

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