One-Pot Catalyst-Free Domino Condensation/Intramolecular 1,3-Dipolar Cycloaddition: Highly Stereoselective Access to Phosphadihydrocoumarin-Fused N,N-Bicyclic Pyrazolidin-3-ones

被引：5
|
作者：
Wu, Mingshu [1 ]
Jiang, Jie [1 ]
Zhu, Zhongxiang [1 ]
Wang, Qinghe [1 ]
Kong, Dulin [2 ]
机构：
[1] Hainan Normal Univ, Coll Chem & Chem Engn, Key Lab Trop Med Plant Chem, Minist Educ, Haikou 571158, Hainan, Peoples R China
[2] Hainan Med Univ, Sch Pharmaceut Sci, Haikou 571199, Hainan, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2018年 / 50卷 / 01期
关键词：
catalyst-free; stereoselectivity; nitrogen and phosphorus heterocycles; polycycles; intramolecular cycloaddition; AZOMETHINE IMINES; ASYMMETRIC-SYNTHESIS; ACID; DESIGN; YLIDES; PHOSPHACOUMARINS; PEPTIDOMIMETICS; IDENTIFICATION; INHIBITORS; ANALOGS;
D O I：
10.1055/s-0036-1590896
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A concise, atom-economic, and highly regio/stereoselective synthetic strategy was developed for the construction of phosphorus- and nitrogen-fused polycyclic skeleton derivatives. The one-pot, two-step, catalyst-free domino condensation/intramolecular cycloaddition reaction of various substituted 2-(vinylphosphoryloxy)benzaldehydes with pyrazolidin-3-one took place at room temperature. Three new bonds (C-C, 2 x C-N) and two new nitrogen and phosphorus heterocycles were simultaneously constructed. The reaction is particularly attractive due to features such as low cost, mild conditions, atom economy, high stereoselectivity, and potential biological activity of the product.
引用
收藏
页码：139 / 145
页数：7
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