由α-重氮吡唑酰胺和邻羟基醛胺催化银催化正[2 + 4]环加成非对映选择性合成空间位阻4-氨基铬-2-酮。

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-07-02 DOI:10.1021/acs.joc.5c00747

Pei Li,Maoqing Shi,Kaixin Yang,Kongxi Qiu,Zhonghui Zhang,Yaxin Li,Xiaoyan Yang,Xiang Fu,Ji Zhang,Wenhao Hu,Yu Qian

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引用次数: 0

摘要

4-氨基铬-2- 1衍生物是许多药物和生物活性化合物的重要支架。本文描述了α-重氮吡唑酰胺和邻羟基芳香醛胺之间的ag催化[2 + 4]环加成反应，快速合成了具有高收率和优异非对映选择性的取代4-氨基铬-2- 1衍生物。该方法的特点是底物范围广，反应条件温和，能够产生对选定肿瘤细胞系具有显著抗肿瘤活性的产物。

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Ag-Catalyzed Formal [2 + 4] Cycloaddition for the Diastereoselective Synthesis of Sterically Hindered 4-Aminochroman-2-ones from α-Diazopyrazoleamides and o-Hydroxy Aldimines.

4-Aminochroman-2-one derivatives serve as crucial scaffolds in numerous pharmaceuticals and bioactive compounds. Here, we describe an efficient Ag-catalytic [2 + 4] cycloaddition reaction between α-diazo pyrazoleamides and o-hydroxy aromatic aldimines for the rapid synthesis of substituted 4-aminochroman-2-one derivatives with high yield and excellent diastereoselectivity. This method features a broad substrate scope, mild reaction conditions, and the ability to generate products exhibiting notable antitumor activity against selected tumor cell lines.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.