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Synthesis 2013; 45(15): 2193-2200
DOI: 10.1055/s-0033-1338487
DOI: 10.1055/s-0033-1338487
paper
Convenient One-Pot Three-Component Synthesis of Trifluoromethylated Tetrahydrobenzo[g]chromene Derivatives
Further Information
Publication History
Received: 13 March 2013
Accepted after revision: 08 May 2013
Publication Date:
13 June 2013 (online)
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 systemsSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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