Aledwan Hajar, Zimmermann Guy, Fridman Natalia, Vassilikogiannakis Georgios, Saady Abed
Department of Chemistry, Bar-Ilan University, Ramat-Gan, 52900, Israel.
Schulich Faculty of Chemistry, Technion-Israel Institute of Technology, Haifa City 3200003, Israel.
Org Lett. 2025 Jul 18;27(28):7513-7517. doi: 10.1021/acs.orglett.5c01807. Epub 2025 Jul 8.
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.
我们报道了一种从易于获得的N-取代α-氨基酸温和、无金属合成2,5-二取代噻唑的方法。该反应通过用亚硫酰氯活化羧酸，随后进行分子内环化和原位亚砜脱氧，以优异的产率得到目标噻唑。这种无过渡金属、稳健且可扩展的方案能够合成多种2,5-二取代噻唑，无需复杂试剂，显著简化了其合成过程。
