NaHCO3-promoted Formal [4+3] Annulation of Salicylaldehydes with Isoquinolinium Salts Accessing Isoquinoline-fused Benzo[f][1,3]oxazepines

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-11-13 DOI:10.1002/adsc.202401295

Qiang Tang, Yanan Liu, Mengdi Wu, Yangzilin Kong, Xiaochun Jiang, Shizhang Ling, Yongjia Shang, Xinwei He

引用次数: 0

Abstract

A concise and practical sustainable strategy for modular access to isoquinoline-fused benzo[f][1,3]oxazepine derivatives through a formal [4+3] annulation of commercially available salicyaldehydes with isoquinolinium salts has been developed. The reactions proceeded through the formation of two new bonds (C=C and C-O) and a seven-membered heterocyclic ring in one pot. Remarkably, use of simple NaHCO3 as a mild base, open atmosphere, nonhazardous reagents, nice functional group tolerance, and easily scale up are added characteristics to this approach. A wide range of substrates are compatible with this mild reaction system, thereby proving a facile and reliable protocol for constructing a benzo[f][1,3]oxazepine skeletons.

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NaHCO3 促进水杨醛与异喹啉盐的正规 [4+3] 连接，获得异喹啉融合的苯并[f][1,3]氧氮杂卓

通过市售水杨醛与异喹啉鎓盐的正式[4+3]环化反应，开发出一种简洁实用的可持续战略，以模块化方式获得异喹啉融合的苯并[f][1,3]氧氮杂卓衍生物。反应在一锅内形成两个新键（C=C 和 C-O）和一个七元杂环。值得注意的是，使用简单的 NaHCO3 作为温和的碱、开放的气氛、非危险试剂、良好的官能团耐受性和易于扩展是这种方法的额外特点。这种温和的反应体系兼容多种底物，从而证明了构建苯并[f][1,3]氧氮杂卓骨架的方案简便可靠。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.