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Synthesis
DOI: 10.1055/a-2360-8167
paper
Special Topic Dedicated to Prof. H. Ila

Palladium-Catalyzed Domino Heteroarylation of Thioamides: A Simple Route to Benzothieno[2,3-b]quinolones

Manojkumar Janni
,
Annaram Thirupathi
,
Subhashini V. Subramaniam
,
Saravanan Peruncheralathan∗
This work was supported by the Department of Atomic Energy, Government of India.
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Abstract

Domino reactions are essential for advancing organic synthesis. This study introduces novel thioamide-based precursors for a palladium-catalyzed selective domino heteroarylation process. The method efficiently produces benzothieno[2,3-b]quinolones with yields ranging from moderate to very good. By employing aryl chlorides, the efficiency of the domino hetero-annulation process is comparable to that of aryl bromides. Executing a one-pot, two-step reaction also delivered a single domino product with high selectivity. The strategy involved fine-tuning substituent reactivity, utilizing electron-rich arenes, and forming metallocycles with nucleophilic sulfur, consistently yielding a single product. The proposed mechanism is corroborated by mechanistic studies.

Key words

domino reaction - benzothiophene - palladium - selective C–S and C–N bond formation

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2360-8167.
  • Supporting Information


Publication History

Received: 07 June 2024

Accepted after revision: 04 July 2024

Accepted Manuscript online:
04 July 2024

Article published online:
29 July 2024

© 2024. Thieme. All rights reserved

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