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STUDIES ON AROMATIC NITRO COMPOUNDS. I. REACTION OF 6-NITROQUINOLINE WITH ACTIVE METHYLENE COMPOUNDS IN THE PRESENCE OF BASES
Tomioka, Yukihiko,Mochiike, Akihumi,Himeno, Junko,Yamazaki, Motoyoshi
, p. 1286 - 1291 (2007/10/02)
The reactions of 6-nitroquinoline (I) with some cyanomethylene compounds in the 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) i 56 and 6.3percent 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 (66.5percent).Similarly, the reactions of I with methyl cyanoacetate, p-nitrophenylacetonitrile, ω-cyanoacetophenone and 1-cyanoetylpyrrolidine 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.Keywords: 6-nitroquinoline; base; cyanomethylene compounds; 6-acylaminoquinoline-5-carbonitriles; hydrolysis; 6-aminoquinoline-5-carbonitrile; acid chlorides
