A Convenient and Efficient Synthesis of Coumarin-Containing Phthalides and Derivatives

Shao-Chun Shen; Xing-Wen Sun; Guoqiang Lin

doi:10.1055/s-0032-1316871

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(9): 1181-1190
DOI: 10.1055/s-0032-1316871

paper

A Convenient and Efficient Synthesis of Coumarin-Containing Phthalides and Derivatives

Shao-Chun Shen

^aDepartment of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, P. R. of China Fax: +86(21)65642406 eMail: sunxingwen@fudan.edu.cn

,

Xing-Wen Sun*

^aDepartment of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, P. R. of China Fax: +86(21)65642406 eMail: sunxingwen@fudan.edu.cn

,

Guoqiang Lin*

^aDepartment of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, P. R. of China Fax: +86(21)65642406 eMail: sunxingwen@fudan.edu.cn

^bKey Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China eMail: lingq@mail.sioc.ac.cn

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Abstract

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Abstract

A highly efficient and convenient procedure to access a series of coumarin-containing phthalides and derivatives is developed. The novel bis-heterocyclic products are obtained via reactions between 4-hydroxycoumarins (or 4-hydroxy-2-quinolones) with different 2-formylbenzoic acids in water as an environmentally friendly solvent. 4-Aryl substituted derivatives of 3-(4-hydroxy)coumarinylphthalide are obtained in excellent yields by initial conversion into the corresponding triflate and subsequent palladium-catalyzed Suzuki–Miyaura coupling with arylboronic acids.

Key words

coumarins - phthalides - bis-heterocyclic - water - Suzuki–Miyaura coupling

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