通过铜（II）介导的 o-氨基苯乙酮和芳基硼酸的接力反应合成吖啶酮。

Syntheses of Acridones via Copper(II)-Mediated Relay Reactions from o-Aminoacetophenones and Arylboronic Acids.

机构信息

Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, School of Chemistry and Chemical Engineering , Henan Normal University , Xinxiang , Henan 453007 , China.

出版信息

Org Lett. 2018 May 18;20(10):2897-2901. doi: 10.1021/acs.orglett.8b00957. Epub 2018 Apr 26.

DOI:10.1021/acs.orglett.8b00957

PMID:29697264

Abstract

The reaction of o-aminoacetophenones and arylboronic acids catalyzed by copper(II) salts in the presence of pyridine under an O atmosphere provides a general and efficient one-pot preparation of biologically interesting acridones. This relay reaction comprises an intermolecular Suzuki cross-coupling, intramolecular oxidative C(sp)-H amination, and C(sp)-H activation with simultaneous rearrangement of the generated isatin intermediates. This strategy tolerates both electron-donating and -withdrawing functionalities to afford various acridones in good to excellent yields.

摘要

在氧气氛围下，铜(II)盐在吡啶存在下催化邻氨基苯乙酮和芳基硼酸的反应，提供了一种通用且高效的一锅法制备具有生物意义的吖啶酮的方法。该接力反应包括分子间的铃木交叉偶联、分子内的氧化 C(sp)-H 氨化以及同时重排生成的靛红中间体的 C(sp)-H 活化。该策略对供电子和吸电子官能团都具有耐受性，能够以良好到优秀的收率得到各种吖啶酮。