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

Synthesis Pub Date : 2024-07-04 DOI:10.1055/a-2360-8167
M. Janni, Annaram Thirupathi, Subhashini V Subramanian, S. Peruncheralathan
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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 heteroannulation 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.

Abstract Image

钯催化的多米诺硫酰胺异芳基化反应:获得苯并噻吩并[2,3-b]喹啉酮的简单途径
多米诺反应对于推进有机合成至关重要。本研究介绍了用于钯催化选择性多米诺杂芳基化过程的新型硫代酰胺基前体。该方法可高效生产苯并噻吩并[2,3-b]喹啉酮类化合物,产率从中等到非常好不等。通过使用芳基氯化物,多米诺杂芳基化过程的效率与芳基溴化物相当。执行一锅两步反应还能得到高选择性的单一多米诺产物。该策略包括微调取代基反应性、利用富电子烯烃以及与亲核硫形成金属环,从而持续产生单一产物。机理研究证实了所提出的机理。
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