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Synthesis 2013; 45(15): 2193-2200
DOI: 10.1055/s-0033-1338487
paper
© Georg Thieme Verlag Stuttgart · New York

Convenient One-Pot Three-Component Synthesis of Trifluoromethylated Tetrahydrobenzo[g]chromene Derivatives

Yijun Duan
a   Department of Chemistry, School of Science, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China   Fax: +86(21)66134594   Email: lpsong@shu.edu.cn
,
Xu Wang
a   Department of Chemistry, School of Science, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China   Fax: +86(21)66134594   Email: lpsong@shu.edu.cn
,
Xiaoling Xu
a   Department of Chemistry, School of Science, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China   Fax: +86(21)66134594   Email: lpsong@shu.edu.cn
,
Zhangping Kang
a   Department of Chemistry, School of Science, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China   Fax: +86(21)66134594   Email: lpsong@shu.edu.cn
,
Min Zhang
a   Department of Chemistry, School of Science, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China   Fax: +86(21)66134594   Email: lpsong@shu.edu.cn
,
Liping Song*
a   Department of Chemistry, School of Science, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China   Fax: +86(21)66134594   Email: lpsong@shu.edu.cn
b   Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, P. R. of China
,
Hongmei Deng
c   Laboratory for Microstructures, Shanghai University, 354 Fenglin Lu, Shanghai 200032, Shanghai 200444, P. R. of China
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Publication History

Received: 13 March 2013

Accepted after revision: 08 May 2013

Publication Date:
13 June 2013 (online)

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Abstract

A series of ethyl 4-(het)aryl-5,10-dioxo-2-hydroxy-2-(trifluoromethyl)-3,4,5,10-tetrahydro-2H-benzo[g]chromene-3-carboxylates were efficiently synthesized from 2-hydroxynaphthoquinone, aromatic aldehydes, and ethyl 4,4,4-trifluoro-3-oxobutanoate by a one-pot multicomponent reaction catalyzed by the combination of ammonium acetate and acetic acid. The benzochromenes are presumably formed through an initial Knoevenagel condensation followed by a Michael addition and regioselective intramolecular annulation. The dehydration reaction of the hemiketal moiety to the corresponding dehydrated product was also studied.

Key words

multicomponent reactions - quinones - aldehydes - cyclizations - heterocycles - catalysis - fluorine - fused-ring systems

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