1,2-Dichloroethane as a Gaseous Acetylene Source for the Rapid Assembly of Isoquinolino[1,2-b]quinazolinone Scaffolds

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-09 DOI:10.1021/acs.orglett.5c00925

Xinxin Zhu, Mengyao Shi, Cuilian Xu, Xiaoping Xue, Lijun Zhang, Liangxin Fan

引用次数: 0

Abstract

Reported herein is a novel ruthenium(II)-catalyzed [4 + 2] annulation of quinazolinones with 1,2-dichloroethane (DCE), resulting in a myriad of isoquinolino[1,2-b]quinazolinone scaffolds. In this protocol, DCE serves not only as a solvent but also as an acetylene source. The fused quinazolinones undergo versatile transformations and provide a rapid and convenient way to access several important bioactive molecule analogues such as Rutecarpine, Euxylophoricine B and Euxylophoricine E. The potential reaction pathway was elucidated through detailed mechanistic studies and Density Functional Theory (DFT) calculations.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.