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I2‐Promoted Oxidative Annulation of Deoxybenzoin‐Chalcone Adduct: Temperature‐Controlled Access to Tetrasubstituted 2,3‐trans‐Dihydrofurans and Furans
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2024-04-23 , DOI: 10.1002/adsc.202400304
Thi Thanh Nhan Vu 1 , Thu Ngoc Trinh 1 , Thu Trang Pham 1 , Minh Tu Ha 1 , Dinh Hung Mac 1 , pascal retailleau 2 , Thanh Binh Nguyen 2
Affiliation  

Tetrasubstituted 2,3‐trans‐dihydrofuran and furan are important heterocyclic scaffolds in natural product, bioorganic and medicinal chemistry as well as in material science. The synthesis of both of these heterocycles starting from common and readily available starting materials are challenging. We found that in situ generated deoxybenzoin‐chalcone Michael adducts underwent oxidative annulation upon heating with molecular iodine in DMSO to provide selectively 2,3‐trans‐dihydrofurans at 80 °C and furans at 120 °C.

中文翻译:

I2-促进脱氧安息香-查尔酮加合物的氧化环化:温度控制获得四取代的2,3-反式二氢呋喃和呋喃

四取代的2,3-反式二氢呋喃和呋喃是天然产物、生物有机和药物化学以及材料科学中重要的杂环支架。从常见且容易获得的起始材料开始合成这两种杂环化合物具有挑战性。我们发现,原位生成的脱氧安息香-查耳酮迈克尔加合物在 DMSO 中与分子碘一起加热时发生氧化环化,在 80 °C 下选择性地提供 2,3-反式二氢呋喃,在 120 °C 下选择性地提供呋喃。
更新日期:2024-04-23
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