A single pot organocatalytic diastereoselective synthesis of fluorescent ring fused 2-pyridone decalines via a domino Knoevenagel/Michael/hydro-lactamisation sequence

被引：1

作者：

Kamble, Sumit B. ^{[1
,2
,3
]}

Bhore, Ranjeet K. ^{[1
]}

Tilve, Santosh G. ^{[3
]}

机构：

[1] Cent Salt & Marine Chem Res Inst, Dept Salt & Marine Chem, Gijubhai Badekha Marg,Waghawadi Rd, Bhavnagar 364002, Gujarat, India

[2] Acad Sci & Innovat Res (AcSIR, Uttar Pradesh 201002, India

[3] Goa Univ, Sch Chem Sci, Taleigao Plateau, Goa 403206, India

来源：

ORGANIC CHEMISTRY FRONTIERS | 2021年 / 8卷 / 18期

关键词：

CASCADE SYNTHESIS; MULTICOMPONENT; CONSTRUCTION; DERIVATIVES; INHIBITORS; HUPERZINE; FUNGUS;

D O I：

10.1039/d1qo00582k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Multifunctional ring fused octahydro 3-CN-2-pyridone decaline motifs are constructed by a single pot multicomponent, diastereoselective, organocatalytic domino approach. Three consecutive catalytic reaction sequences are presented, wherein l-proline plays a catalytic dual role for Knoevenagel condensation and Michael addition co-operatively with PhCOOH, followed by annulation by hydro-lactamisation. Compounds containing bromine, chlorine, methoxy and methylenedioxy groups showed aggregation-induced fluorescence under long-range UV exposure. The present method is a green synthetic strategy with the following features: high diastereoselectivity (dr > 20), catalytic activity, high yields, cost-effective nature, a simple, mild, and operationally scalable process, and broad substrate scope.

引用

页码：5032 / 5039

页数：8