Thiourea-Promoted Cascade Dihalogenation-Cyclization of Cyclohexadienone-Containing 1,6-Enynes,Advanced Synthesis & Catalysis

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Thiourea-Promoted Cascade Dihalogenation-Cyclization of Cyclohexadienone-Containing 1,6-Enynes
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2023-01-18 , DOI: 10.1002/adsc.202201185
Jia-Ying Zhao ₁ , Qi Liao ₁ , Jian-Wei Zhang ₁ , Guo-Qiang Lin ₂ , Zhengtao Wang ₁ , Dingding Gao ₃ , Qinghua Li ₃ , Ping Tian ₄

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Organohalogens play an important role in the drug discovery and functional materials. However, the convenient preparation of organohalogens still remains a challenging task. Herein, we report a metal-free cascade dihalogenation-cyclization of cyclohexadienone-containing 1,6-enynes in a biodegradable solvent to generate the dibrominated cis-tetrahydrobenzofuran-5(4H)-ones and cis-dihydrobenzopyran-6(5H)-ones respectively bearing 1,4-dibromobut-1-enyl subunit in trans-trans and trans-cis form. A subgram-scale experiment and several downstream transformations are presented for elaborating the synthetic utility. Moreover, the potent anticancer activity is observed against MDA-MB-468 cells for the corresponding products.

中文翻译：

硫脲促进含环己二烯酮 1,6-烯炔的级联二卤化-环化

有机卤素在药物发现和功能材料方面发挥着重要作用。然而，有机卤素的便捷制备仍然是一项具有挑战性的任务。在此，我们报道了含环己二烯酮的 1,6-烯炔在可生物降解溶剂中的无金属级联二卤化环化反应，生成二溴代顺式-四氢苯并呋喃-5(4 H)-酮和顺式-二氢苯并吡喃-6(5 H ) - 分别带有 1,4-dibromobut-1-enyl 亚基的反式-反式和反式-顺式形式。提出了亚克级实验和几个下游转换以详细说明合成效用。此外，观察到相应产品对 MDA-MB-468 细胞具有有效的抗癌活性。

更新日期：2023-01-18

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