Studies on aromatic nitro compounds. I. Reaction of 6-nitroquinoline with active methylene compounds in the presence of bases.

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The reactions of 6-nitroquinoline (I) with some cyanomethylene compounds in the presence of a base were investigated. I reacted with ethyl cyanoacetate in the presence of potassium cyanide to produce 6-ethoxalylaminoquinoline-5-carbonitrile (IIa) and diethyl 2-cyano-3-(5-cyano-6-quinolylamino) fumarate (IIIa) in 56 and 6.3% yields, respectively. When potassium tert-butoxide or potassium hydroxide was used as a base, IIa was obtained as a sole product. Potassium hydroxide was the most effective in the formation of IIa (66.5%). Similarly, the reactions of I with methyl cyanoacetate, p-nitrophenylacetonitrile, ω-cyanoacetophenone and 1-cyanoacetylpyrrolidine in the presence of potassium hydroxide gave the 6-aminoquinoline-5-carbonitrile derivatives (IIb, IIc, IId and IIf) corresponding to IIa. In the reaction of I with α-cyanoacetamide, α-cyano-β-carbamoyl-β-(5-cyano-6-quinolylamino) acrylamide (IIIe) and 3-cyano-4-(5-cyano-6-quinolylamino)-1H-pyrrole-2, 5-dione (VI) were obtained as minor products together with IIe.

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