1. Practical access to fluorescent 2,3-naphthalimide derivatives via didehydro-Diels–Alder reaction
- Author
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Yuling Lu, Zengwei Luo, Chunmei Chen, Hucheng Zhu, Cheng Zhong, Xia Chen, Meng Yao, Yonghui Zhang, and Zhenhua Guan
- Subjects
Fluorophore ,Metals and Alloys ,Substrate (chemistry) ,General Chemistry ,Fluorescence ,Combinatorial chemistry ,Catalysis ,Surfaces, Coatings and Films ,Electronic, Optical and Magnetic Materials ,chemistry.chemical_compound ,chemistry ,Intramolecular force ,Functional group ,Materials Chemistry ,Ceramics and Composites ,Moiety ,Waste disposal ,Diels–Alder reaction - Abstract
A practical and efficient approach for the synthesis of fluorescent 2,3-naphthalimide derivatives has been developed from readily available starting materials via an intramolecular didehydro-Diels-Alder reaction, which proceeded well under room temperature, exhibiting a wide substrate scope and good functional group tolerance. The practicability of this methodology has been verified by one-step synthesis of the environmentally sensitive fluorophore 6-DMN on a gram scale with a shorter time, fewer steps and less waste disposal, and without the utilization of toxic transition metals. The present experimental and computational studies support the crucial role of the propiolimide moiety in the transformation.
- Published
- 2021