Synthesis 2025; 57(01): 229-239
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.
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
© 2024. Thieme. All rights reserved
Georg Thieme Verlag KG
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