亲电试剂促进 - 芳基取代炔酰胺的环化反应：构建 3-氨基-4-卤代或 4-硒代异香豆素衍生物。

Electrophile promoted cyclization of -aryl substituted ynamides: construction of 3-amino-4-halo- or 4 seleno-isocoumarin derivatives.

机构信息

Institute of Organic and Analytical Chemistry, ICOA UMR 7311 CNRS, Université d'Orléans, Pôle de chimie, Rue de Chartres, 45100 Orléans, France.

Institut de Chimie des Substances Naturelles, UPR 2301, CNRS, Gif-sur-Yvette, France.

出版信息

Org Biomol Chem. 2021 Aug 5;19(30):6623-6627. doi: 10.1039/d1ob01075a.

DOI:10.1039/d1ob01075a

PMID:34282818

Abstract

Isocoumarins are important building blocks in medicinal chemistry. They are widespread in the core structure of biologically active compounds. Here we report the development of an efficient and highly reactive electrophilic cyclization of ortho-ynamidyl benzoate esters providing access to 3-amino-4-halo- or 4-seleno-isocoumarins in a short time (<1 min) with good yields.

摘要

异香豆素是药物化学中的重要构建模块。它们广泛存在于具有生物活性的化合物的核心结构中。在这里，我们报告了邻炔胺基苯甲酸酯酯的高效和高反应性的亲电环化反应的发展，该反应可在短时间（<1 分钟）内以良好的收率获得 3-氨基-4-卤代或 4-硒代异香豆素。