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Synthesis 2018; 50(18): 3708-3714
DOI: 10.1055/s-0037-1610123
paper
© Georg Thieme Verlag Stuttgart · New York

An Efficient and Ecofriendly Three-Component Reaction for the Rapid Synthesis of 2-Amino-4H-chromenes Catalyzed by a DABCO­-Based Ionic Liquid

Cheng-Bin Li
National Engineering Research Center of Pesticide (Tianjin), State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People’s Republic of China   eMail: xudazhen@nankai.edu.cn
,
Yu-Wei Li
National Engineering Research Center of Pesticide (Tianjin), State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People’s Republic of China   eMail: xudazhen@nankai.edu.cn
,
Da-Zhen Xu*
National Engineering Research Center of Pesticide (Tianjin), State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People’s Republic of China   eMail: xudazhen@nankai.edu.cn
› InstitutsangabenThis work was financially supported by the National Natural Science Foundation of China (NSFC) (No. 21302101), and National Training Programs of Innovation and Entrepreneurship for Undergraduates (Nos. 201710055080, 201710055085). We also thank the Nankai University State Key Laboratory of Elemento-Organic Chemistry for support.
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Publikationsverlauf

Received: 11. April 2018

Accepted after revision: 17. Mai 2018

Publikationsdatum:
02. Juli 2018 (online)

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Abstract

An efficient, economical, and green strategy for the construction of biologically relevant 2-amino-4H-chromene scaffolds via a tandem Knoevenagel–Pinner cyclization–Michael reaction has been successfully developed. In the presence of DABCO-based ionic liquids, two different 2-amino-4H-chromene derivatives, 2-amino-4-(indol-3-yl)-4H-chromenes and 2-amino-4-(pyrazol-4-yl)-4H-chromenes, were prepared in good to excellent yields (81–97%) within short reaction times under mild conditions. All the products are purified by simple crystallization. The catalyst could be recycled for at least five times.

Key words

2-amino-4H-chromene - green chemistry - ionic liquid - multicomponent reaction - salicylaldehyde

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610123.
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