Sequential Cu-catalyzed amidation-base-mediated camps cyclization:: A two-step synthesis of 2-aryl-4-quinolones from o-halophenones
Sequential Cu-catalyzed amidation-base-mediated camps cyclization:: A two-step synthesis of 2-aryl-4-quinolones from o-halophenones
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DOI：
10.1021/jo701384n
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发表时间：
2007-10-12
影响因子：
3.6
通讯作者：
Buchwald, Stephen L.
中科院分区：
文献类型：
--
作者：
Jones, Carrie P.;Anderson, Kevin W.;Buchwald, Stephen L.
描述了制备 2-芳基-和 2-乙烯基-4-喹诺酮的直接两步法，该方法利用铜催化的邻卤苯酮酰胺化，然后对所得 N-(2-酮芳基)酰胺进行碱促进的 Camps 环化。使用 CuI、二胺配体和碱作为催化剂体系，一系列芳基、杂芳基和乙烯基酰胺的酰胺化反应都能以良好的产率进行。随后的 Camps 环化在所描述的条件下有效地提供了所需的 4-喹诺酮。
A direct two-step method for the preparation of 2-aryl- and 2-vinyl-4-quinolones that utilizes a copper-catalyzed amidation of o-halophenones followed by a base-promoted Camps cyclization of the resulting N-(2-ketoaryl)amides is described. With CuI, a diamine ligand, and base as the catalyst system, the amidation reactions proceed in good yields for a range of aryl, heteroaryl, and vinyl amides. The subsequent Camps cyclization efficiently provides the desired 4-quinolones with the conditions that are described.