Tandem Michael Addition–Cyclization of Nitroalkenes with 1,3-Dicarbonyl Compounds Accompanied by Removal of Nitro Group,The Journal of Organic Chemistry

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Tandem Michael Addition–Cyclization of Nitroalkenes with 1,3-Dicarbonyl Compounds Accompanied by Removal of Nitro Group
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-09-08 , DOI: 10.1021/acs.joc.1c01586
Zhizhao Wang ₁ , Guoren Yue ₁ , Xiangdong Ji ₂ , Hai Song ₂ , Penji Yan ₂ , Jixing Zhao ₃ , Xin Jia ₁

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A tandem Michael addition–cyclization of nitroalkenes with 1,3-dicarbonyl compounds was developed using phase transfer catalyst (PTC), allowing for the synthesis of polysubstituted-[4,5]-dihydrofuran in high yields. A wide range of substrates were demonstrated by this one-step process. Meanwhile, nitro group was substituted to form corresponding nitrite ion detected in the aqueous phase providing a reasonable pathway for denitrating poisonous and explosive nitro-containing compounds. The proposed mechanism was also supported by our DFT calculations.

中文翻译：

1,3-二羰基化合物脱硝基团的硝基烯烃串联迈克尔加成环化

使用相转移催化剂 (PTC) 开发了硝基烯烃与 1,3-二羰基化合物的串联迈克尔加成环化，允许以高产率合成多取代-[4,5]-二氢呋喃。这种一步法展示了广泛的基材。同时，硝基被取代形成相应的亚硝酸根离子，在水相中检测到，为有毒和爆炸性含硝基化合物的脱硝提供了合理的途径。我们的 DFT 计算也支持了所提出的机制。

更新日期：2021-10-15

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