Preparation of 5-Cyano-4,6-dimethyl-2H-pyran-2-one and 3-Cyano-5-methoxy-4-methyl-5H-furan-2-one via a One-Pot,Domino-Knoevenagel Process |
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Authors: | Prativa B S Dawadi Johan Lugtenburg |
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Institution: | 1. Leiden Institute of Chemistry, Leiden University , Leiden, The Netherlands p.dawadi@chem.leidenuniv.nl;3. Leiden Institute of Chemistry, Leiden University , Leiden, The Netherlands |
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Abstract: | 5-Cyano-4,6-dimethyl-2H-pyran-2-one (1) has been prepared via a simple one-pot domino-Knoevenagel reaction starting from ethyl acetoacetate (2) and cyanoacetone (3). Similarly, a new racemic 3-cyano-5-methoxy-4-methyl-5H-furan-2-one (7) has been prepared from 1,1-dimethoxyacetone (6) and cyanoacetic acid (4). The new alkylidene derivatives (Z/E)-ethyl-4-cyano-3-methylbut-3-enoate (5), (Z/E)-ethyl 5-amino-4-cyano-3-methyl-5-oxopent-3-enoate (9), and (2,2-dimethoxy-1-methylethylidene)malononitrile (11) have been prepared via the Knoevenagel reactions. The easy access to these new compounds in good yields shows that ammonium acetate/acetic acid–catalyzed Knoevenagel reactions and domino-Knoevenagel reactions have a broad scope of application. |
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Keywords: | (2 2-Dimethoxy-1-methylethylidene)malononitrile (Z/E)-ethyl 5-amino-4-cyano-3-methyl-5-oxopent-3-enoate (Z/E)-ethyl 4-cyano-3-methylbut-3-enoate NMR spectroscopy |
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