Synthesis 2012; 44(15): 2385-2395
DOI: 10.1055/s-0031-1289810
paper
© Georg Thieme Verlag Stuttgart · New York

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

Chao-Yue Chen
a   School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. of China
,
Yong-Sheng Zhao
a   School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. of China
,
Chang-Bing Xiang
a   School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. of China
,
Zhi-Zhen Huang*
a   School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. of China
b   Department of Chemistry, Zhejiang University, Hangzhou 310028, P. R. of China, Fax: +86(25)83686240   Email: huangzz@nju.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 10 April 2012

Accepted after revision: 14 May 2012

Publication Date:
04 July 2012 (online)


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.

Supporting Information

 
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