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Synthesis 2024; 56(11): 1799-1806
DOI: 10.1055/a-2259-3283
paper

Access to 8-Aminoindolizine Fused with Quinone via Cu(OAc)2-Catalyzed Domino [4+2] Annulation

Sunhee Lee‡
,
Yechan Lee‡
,
Wan Namkung∗
,
Ikyon Kim∗
We thank the National Research Foundation of Korea (NRF-2018R1A6A1A03023718 and NRF-2020R1A2C2005961) for generous financial support.
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Abstract

Cu(OAc)2-catalyzed [4+2] annulation of N-substituted pyrrole-2-carbonitriles with quinones allowed access to a wide range of 8-aminoindolizines fused with quinones through a domino process involving a sequence of intermolecular Michael addition, Thorpe–Ziegler type cyclization, and aromatization. Biological evaluation of the resulting quinone-8-aminoindolizine hybrids revealed significant anticancer effects of these compounds in human hepatocellular cells (HepG2) and prostate adenocarcinoma cells (PC-3).

Key words

chemical space - quinone - indolizine - hybrid structure - domino reaction - diversity-oriented synthesis - atom-economy - anticancer activity

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2259-3283.
  • Supporting Information


Publication History

Received: 12 January 2024

Accepted after revision: 01 February 2024

Accepted Manuscript online:
01 February 2024

Article published online:
19 February 2024

© 2024. Thieme. All rights reserved

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