Organocatalytic Enantioselective Synthesis of Oxindole-4-Aminopyrazolone Derivatives via Mannich Reaction of 3-Substituted Oxindoles With Pyrazolinone Ketimines

IF 2 3区化学 Q2 CHEMISTRY, ORGANIC

Journal of Heterocyclic Chemistry Pub Date : 2025-06-30 DOI:10.1002/jhet.70005

María E. Molinero, Sandra Tejedor, Laura Martín, Alicia Maestro, José M. Andrés

引用次数: 0

Abstract

The organocatalyzed Mannich reaction between pyrazolinone ketimines and 3-aryl-substituted oxindoles mediated by a hidroquinine-derived squaramide is reported. This method enables the synthesis of a diverse set of oxindole-4-aminopyrazolone derivatives bearing vicinal tetrasubstituted stereocenters, affording products in good yields (up to 95%), with excellent diastereoselectivity (> 20:1) and moderate enantioselectivity (up to 85:15 er) under mild conditions.

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3-取代氧吲哚与吡唑啉酮酮曼尼希反应有机催化对映选择性合成氧吲哚-4-氨基吡唑酮衍生物

报道了吡唑啉酮酮酮与3-芳基取代氧吲哚之间的曼尼希有机催化反应。该方法可以合成多种含有邻四取代立体中心的吲哚-4-氨基吡唑酮衍生物，在温和的条件下，产品收率高（高达95%），具有优异的非对映选择性（20:1）和中等的对映选择性（高达85:15 er）。

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

Journal of Heterocyclic Chemistry 化学-有机化学

CiteScore

5.20

自引率

4.20%

发文量

177

审稿时长

3.9 months

期刊介绍： The Journal of Heterocyclic Chemistry is interested in publishing research on all aspects of heterocyclic chemistry, especially development and application of efficient synthetic methodologies and strategies for the synthesis of various heterocyclic compounds. In addition, Journal of Heterocyclic Chemistry promotes research in other areas that contribute to heterocyclic synthesis/application, such as synthesis design, reaction techniques, flow chemistry and continuous processing, multiphase catalysis, green chemistry, catalyst immobilization and recycling.