通过铑(III)催化的(4 + 2)环加成反应合成异喹啉酮、1,2-苯并噻嗪和萘并[1',2':4,5]咪唑并[1,2-a]吡啶衍生物。

Synthesis of Isoquinolone, 1,2-Benzothiazine, and Naphtho[1',2':4,5]imidazo[1,2-]pyridine Derivatives via Rhodium(III)-Catalyzed (4 + 2) Annulation.

机构信息

School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China.

Department of Chemistry and Biochemistry, Miami University, Oxford, Ohio 45056, United States.

出版信息

J Org Chem. 2022 Sep 2;87(17):11722-11734. doi: 10.1021/acs.joc.2c01376. Epub 2022 Aug 14.

DOI:10.1021/acs.joc.2c01376

PMID:35968716

Abstract

In this study, we report a novel and efficient synthetic method to construct isoquinolone scaffold the Rh(III)-catalyzed (4 + 2) annulation of benzamide with an unreported coupling reagent methyl 2-chloroacrylate. Accordingly, other valuable 1,2-benzothiazine and naphtho[1',2':4,5]imidazo[1,2-]pyridine derivatives are also obtained through a similar synthetic protocol. Thus, our developed method is highlighted by high yield and reaction versatility.

摘要

在这项研究中，我们报告了一种新颖而有效的合成方法，用于构建异喹啉骨架，即通过铑（III）催化的苯甲酰胺与未报道的偶联试剂甲基 2-氯丙烯酸的（4 + 2）环加成反应。相应地，通过类似的合成方案，还获得了其他有价值的 1,2-苯并噻嗪和萘[1',2':4,5]咪唑并[1,2-]吡啶衍生物。因此，我们开发的方法具有高产率和反应多样性的特点。