Bulletin of the Chemical Society of Japan p. 851 - 856 (1991)
Update date:2022-08-12
Topics:
Tsunoda, Katsunori
Yamane, Mitsuyoshi
Nishino, Hiroshi
Kurosawa, Kazu
The reaction of methoxynaphthalenes with malonamide in the presence of manganese(III) acetate gives 2-acetoxy-2-(1-naphthyl)propanediamides and 2-hydroxy-2-(1-naphthyl)propanediamides.It was found that the propanediamidation reaction did occur when naphthalenes have electron-donating substituents, such as a methoxyl group.The reactions of methoxynaphthalenes with ethyl 3-oxobutanoate, 2-cyanoacetamide, and malononitrile in the presence of manganese(III) acetate also yielded the corresponding substituted naphthalenes, ethyl 2-(acetoxymethyl)naphtho<2,1-b>furan-1-carboxylates, and/or a 4-methylene-1(4H)-naphthalenone.The reaction mechanisms are discussed.
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