Synthesis of 6H-Dibenzo[b,d]pyran-6-one Derivatives via Coumarin-Fused Cyclohexa-1,3-diene Intermediates

Chao-Yue Chen; Yong-Sheng Zhao; Chang-Bing Xiang; Zhi-Zhen Huang

doi:10.1055/s-0031-1289810

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(15): 2385-2395
DOI: 10.1055/s-0031-1289810

paper

Synthesis of 6H-Dibenzo[b,d]pyran-6-one Derivatives via Coumarin-Fused Cyclohexa-1,3-diene Intermediates

Chao-Yue Chen

^aSchool of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. of China

,

Yong-Sheng Zhao

^aSchool of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. of China

,

Chang-Bing Xiang

^aSchool of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. of China

,

Zhi-Zhen Huang*

^aSchool of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. of China

^bDepartment of Chemistry, Zhejiang University, Hangzhou 310028, P. R. of China, Fax: +86(25)83686240 eMail: huangzz@nju.edu.cn

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Abstract

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Abstract

In the presence of trifluoroacetic acid and methanesulfonic acid (MSA), a series of monohydric and polyhydric phenols readily undergo a domino Pechmann–dehydration reaction with various 4-hydroxy-6-oxocyclohexane-1,3-dicarboxylates to give 7,8-dihydro-6H-dibenzo[b,d]pyran-6-ones. Subsequent dehydrogenation of the 7,8-dihydro-6H-dibenzo[b,d]pyran-6-ones was performed expediently with DBU/BrCCl₃ to give various 6H-dibenzo[b,d]pyran-6-one derivatives. This strategy has the advantages of inexpensive and easily available raw materials, metal-free procedure, mild reaction conditions, good compatibility with various functional groups, and satisfactory yields.

Key words

6H-dibenzo[b,d]pyran-6-one - 7,8-dihydro-6H-dibenzo[b,d]pyran-6-one - domino Pechmann–dehydration reaction - oxidative dehydrogenation - synthesis

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References

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