Aza-Michael加成法和三氟乙烯氧吲哚内酰胺化法无催化剂合成三氟甲基化五元和七元含氮杂环

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-10-07 DOI:10.1021/acs.joc.5c01670

Jiayuan Liu, , , Anqing Long, , , Junling Zhao*, , and , Juan Li*,

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引用次数: 0

摘要

报道了一种合成三氟甲基化吡唑烷酮和1,5-苯二氮卓酮的新方案。在该策略中，以肼和1,2-二氨基苯为亲核试剂，在无催化剂条件下与isatin衍生的三氟乙烯氧吲哚丙烯酸酯反应，并发生aza-Michael加成/内酰胺化反应，得到相应的产物，收率较高。得到了吡唑烷酮的顺式和反式非对映异构体，并讨论了该反应的可能机理和立体化学性质。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Catalyst-Free Synthesis of Trifluoromethylated Five- and Seven-Membered Nitrogen-Containing Heterocycles via Aza-Michael Addition and Lactamization of Trifluoroethylene Oxindoles

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Catalyst-Free Synthesis of Trifluoromethylated Five- and Seven-Membered Nitrogen-Containing Heterocycles via Aza-Michael Addition and Lactamization of Trifluoroethylene Oxindoles

A novel protocol for the synthesis of trifluoromethylated pyrazolidiones and 1,5-benzodiazepinones was reported. In this strategy, hydrazines and 1,2-diaminobenzenes were used as binucleophiles to react with isatin-derived trifluoroethylene oxindole acrylates under catalyst-free conditions, and an aza-Michael addition/lactamization process occurred to give the corresponding products in good yields. Both cis and trans diastereoisomers of pyrazolidinones were obtained, and the possible mechanism and stereochemistry of this reaction was also discussed.

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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.