N 保护的 5-aminopyrazoles 在常温下的意外脱芳香化：通向高度官能化吡唑的简单途径。

IF 2.7 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2024-08-07 DOI:10.1039/d4ob00879k

Pradeep Natarajan , Arpita Chatterjee , Siddharth Jaya Sajeevan J. , Saravanan Peruncheralathan

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引用次数: 0

摘要

我们介绍了一种在室温下使用高价碘试剂对 5-氨基吡唑进行脱芳烃羟基化反应的新策略。这种方法可在 2 小时内生成一系列 4-羟基-5-氨基吡唑，收率从良好到极佳。此外，我们还展示了合成 4-羟基吡唑酮的多米诺反应。机理研究表明，脱芳烃反应是通过阳离子中间体进行的。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Unexpected dearomatization of N-protected 5-aminopyrazoles at ambient temperature: a simple route to highly functionalized pyrazolines†

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Unexpected dearomatization of N-protected 5-aminopyrazoles at ambient temperature: a simple route to highly functionalized pyrazolines†

We present a new strategy for the dearomatized hydroxylation of 5-aminopyrazoles using a hypervalent iodine reagent at room temperature. This method produces a series of 4-hydroxy-5-iminopyrazolines with good to excellent yields within 2 hours. Additionally, we demonstrate a domino reaction for the synthesis of 4-hydroxy-pyrazolones. Mechanistic studies indicate that the dearomatization proceeds through a cationic intermediate.

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来源期刊

Organic & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.