Studies on Aromatic Nitro Compounds. IV. Reactions of 2-Nitronaphthalenes with Active Methylene Compounds in the Presence of Bases

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The reactions of 2-nitronaphthalenes with active methylene compounds in the presence of a base were investigated. 2-Nitronaphthalene (I) reacted with ethyl cyanoacetate in the presence of potassium hydroxide to produce ethyl N-(1-cyano-2-naphthyl) oxamate (IIa) in 64% yield. Similarly, the reactions of I with methyl cyanoacetate, p-nitrophenyl-acetonitrile, ω-cyanoacetophenone, α-cyanoacetamide and 1-cyanoacetylpyrrolidine in the presence of a base gave the 2-aminonaphthalene-1-carbonitriles (IIb-f) as major products corresponding to IIa. On the other hand, the reaction of 2, 3-dinitronaphthalene (VII) with ethyl cyanoacetate in the presence of potassium hydroxide gave ethyl 2-cyano-2-(3-nitro-1-naphthyl)-acetate (VIIIa). In the reaction of 2-nitronaphthalene-1-carbonitrile (IX) with ethyl cyanoacetate, ethyl 2-cyano-2-(1-cyano-2-naphthyl) acetate (Xa) was obtained.