Construction of 1,4‐Oxazepinones via a Cascade Aza‐Michael/SN2 Annulation of Trifluoromethyl Pyrazole‐Derived Oxadienes with a‐Bromohydroxamates

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry Pub Date : 2024-10-01 DOI:10.1002/ajoc.202400244

引用次数: 0

Abstract

A highly efficient cascade aza‐MIRC (Michael Induced Ring Closure) reaction between trifluoromethylpyrazole (TFPZ)‐derived oxadienes and a‐bromohydroxamates has been developed for the construction of 1,4‐oxazepinone derivatives. The reaction proceeds smoothly under mild conditions via a cascade Aza‐Michael addition/intramolecular S_N2 sequence, and features broad substrate scope, transition‐metal free, operational simplicity etc. The utility of the versatile protocol was also demonstrated by gram‐scale reaction and valuable synthetic transformations.

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通过三氟甲基吡唑衍生恶二烯与 a-溴羟肟酸酯的级联 Aza-Michael/SN2 嵌合反应制备 1,4-氧氮杂卓酮类化合物

为了构建 1,4-氧氮杂卓酮衍生物，我们开发了一种高效的级联氮杂-迈克尔诱导封环（MIRC）反应，该反应在三氟甲基吡唑（TFPZ）衍生的氧杂二烯和 a-溴羟肟酸酯之间进行。该反应在温和条件下通过级联 Aza-Michael 加成/分子内 SN2 顺序顺利进行，具有底物范围广、不含过渡金属、操作简单等特点。克级反应和有价值的合成转化也证明了这一多功能方案的实用性。

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

Asian Journal of Organic Chemistry CHEMISTRY, ORGANIC-

CiteScore

4.70

自引率

3.70%

发文量

372

期刊介绍： Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.