Thiazole-5-carbaldehyde Synthesis by Cascade Annulation of Enaminones and KSCN with Dess–Martin Periodinane Reagent,The Journal of Organic Chemistry

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Thiazole-5-carbaldehyde Synthesis by Cascade Annulation of Enaminones and KSCN with Dess–Martin Periodinane Reagent
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2022-10-19 , DOI: 10.1021/acs.joc.2c01881
Kang Chen ₁ , Baoli Zhao ₂ , Yunyun Liu _{1,

2} , Jie-Ping Wan ₁

Affiliation

The Dess–Martin periodinane (DMP) reagent-mediated reactions of tertiary enaminones with potassium thiocyanate for the synthesis of thiazole-5-carbaldehydes are developed. The product formation involves cascade hydroxyl thiocyanation of the C═C double bond, intramolecular hydroamination of the C≡N bond, and thiazole annulation by condensation on the ketone carbonyl site, representing novel reaction pathways in the reactions between enaminones and thiocyanate salt. DMP plays dual roles in mediating the free radical thiocyanation and inducing the unconventional selective thiazole-5-carbaldehyde formation by masking the in situ generated formyl group during the reaction process.

中文翻译：

戴斯-马丁高碘烷试剂通过烯胺酮和 KSCN 的级联环化合成噻唑-5-甲醛

开发了用于合成噻唑-5-甲醛的叔烯胺酮与硫氰酸钾的戴斯-马丁高碘烷 (DMP) 试剂介导的反应。产物形成涉及C=C双键的级联羟基硫氰化、C≡N键的分子内加氢胺化和通过在酮羰基位点缩合的噻唑环化，代表了烯胺酮与硫氰酸盐之间反应的新反应途径。DMP 在介导自由基硫氰化和通过掩蔽反应过程中原位生成的甲酰基诱导非常规选择性噻唑-5-甲醛形成方面发挥双重作用。

更新日期：2022-10-19

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