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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 19
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Original Articles

Synthesis of Substituted Tetrahydrochromenes by the Reactions of α,β-Unsaturated Cyanoesters with Dimedone/1,3-Cyclohexanedione

, , , , &
Pages 2822-2827 | Received 06 Apr 2010, Published online: 29 Jun 2011
 

Abstract

Ethyl esters of 2-cyano-3-arylacrylic acid 1ad (a = 4-CH3-C6H4-, b = 4-N(CH3)2-C6H4-, c = 2-CH3O-C6H4-, d = 2-Cl-C6H4-) reacted with 5,5-dimethyl-1,3-cyclohexanedione (2p, Y=CH3), and 1eg (e = 4-CH3-C6H4-, f = 2-CH3O-C6H4-, g = 2-Cl-C6H4-) reacted with 1,3-cyclohexanedione (2q, Y=H) in the presence of alcoholic sodium ethoxide to give the corresponding ethyl esters of 2-amino-7,7-dimethyl-5-oxo-4-aryl-5,6,7,8-tetrahydro-4H-chromene-3-carboxylic acid 4ad and 2-amino-5-oxo-4-aryl-5,6,7,8-tetrahydro-4H-chromene-3-carboxylic acid 4eg. The structures of the compounds 4ag were confirmed by their ultraviolet, infrared, 1H NMR, 13C NMR, and mass spectral data and elemental analyses.

ACKNOWLEDGMENT

We are pleased to acknowledge Teruo Shinmyozu, Institute for Materials Chemistry and Engineering, Kyushu University, Japan, for the mass spectrum, NMR, and elemental analyses.

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