Access to 2,5-Disubstituted Thiazoles Via Cyclization of N-Substituted α-Amino Acids.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-07-08 DOI:10.1021/acs.orglett.5c01807

Hajar Aledwan, Guy Zimmermann, Natalia Fridman, Georgios Vassilikogiannakis, Abed Saady

引用次数: 0

Abstract

We report a mild, metal-free synthesis of 2,5-disubstituted thiazoles from readily available N-substituted α-amino acids. The reaction proceeds via carboxylic acid activation with thionyl chloride, followed by intramolecular cyclization and in situ sulfoxide deoxygenation, affording the target thiazoles in excellent yields. This transition-metal-free, robust, and scalable protocol enables access to a broad range of 2,5-disubstituted thiazoles, bypassing the need for complex reagents and significantly simplifying their synthesis.

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通过n -取代α-氨基酸环化制备2,5-二取代噻唑。

我们报道了一种温和的，无金属合成的2,5-二取代噻唑从容易获得的n -取代α-氨基酸。该反应通过羧酸与亚硫酰氯的活化进行，然后进行分子内环化和原位亚砜脱氧，从而获得产率高的目标噻唑。这种不含过渡金属、稳健且可扩展的方案可以获得广泛的2,5-二取代噻唑，无需复杂试剂，并显着简化了它们的合成。

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

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.