Lei Shuang-Gui, Zhou You, Wang Li-Sheng, Yu Zhi-Cheng, Chen Ting, Wu Yan-Dong, Gao Meng, Wu An-Xin
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, P. R. China.
National Engineering Research Center for Tissue Restoration and Reconstruction, Key Laboratory of Biomedical Materials and Engineering of the Ministry of Education, School of Materials Science and Engineering, South China University of Technology, Guangzhou 510006, China.
J Org Chem. 2023 Aug 4;88(15):11150-11160. doi: 10.1021/acs.joc.3c01118. Epub 2023 Jul 18.
A novel multicomponent cascade cyclization reaction in one pot for the preparation of pyrido[3,2-]phenoxazin-5-ones from simple -aminophenols, paraformaldehyde, and enaminones has been established. It is noteworthy that -aminophenol plays multiple roles serving as both a bis-nucleophile and an iminoquinone precursor, which can in situ generate aminophenoxazinones to undergo the Povarov reaction for the first time to yield pyrido[3,2-]phenoxazin-5-ones with a high efficiency. Moreover, the photoluminescence of pyrido[3,2-]phenoxazin-5-ones has polarity sensitivity and features aggregation-induced emission (AIE) characteristics, which is promising for bioimaging and theranostic applications.
已建立了一种新颖的多组分一锅法串联环化反应，用于从简单的对氨基苯酚、多聚甲醛和烯胺酮制备吡啶并[3,2 - ]吩恶嗪 - 5 - 酮。值得注意的是，对氨基苯酚起着多种作用，既是双亲核试剂又是亚氨基醌前体，它能原位生成氨基吩恶嗪酮，首次进行Povarov反应，高效生成吡啶并[3,2 - ]吩恶嗪 - 5 - 酮。此外，吡啶并[3,2 - ]吩恶嗪 - 5 - 酮的光致发光具有极性敏感性，并具有聚集诱导发光（AIE）特性，这在生物成像和诊疗应用方面具有前景。
