78584-83-5Relevant academic research and scientific papers
Studies on Aromatic Nitro Compounds. III. Reaction of 2-Nitronaphtalene and 6-Nitroquinoline with Malononitrile in the Presence of Amine
Ohshima, Toshihiko,Mizuoka, Masae,Tomioka, Yukihiko,Yamazaki, Motoyoshi
, p. 1328 - 1334 (2007/10/02)
The reactions of 2-nitronaphthalene (I) and 6-nitroquinoline (IV) with malononitrile in the presence of an amine were examined.I reacted with malononitrile and morpholine to form 4-(1-cyano-2-naphthylcarbamoyl)morpholine (IIIa) in 43percent yield.When piperidine or pyrrolidine was used in place of morpholine, I yielded the urea derivative (IIIb or IIIc) corresponding to IIIa.From the reaction of I with cyclohexylamine, the urea derivative (IIId) and 2-cyclohexyl-1-imino-3-oxo-1,2,3,4-tetrahydrobenzoquinazoline (VIIId) were obtained in yields of 25 and 24percent, respectively.On the other hand, the reaction of I with benzylamine gave only the quinzoline derivative (VIIIe) corresponding to VIIId.Similarly, IV reacted with malononitrile and an amine to give the corresponding urea and/or quinazoline derivatives (Va-d and/or Xd, e).The structures of III, V, VIII, and X were confirmed by comparison with authentic samples prepared by an alternative route.Keywords - 2-nitronaphthalene; 6-nitroquinoline; amines; malononitrile; urea derivatives; quinazoline derivatives; 2-ethoxycarbonylaminonaphthalene-1-carbonitrile; 6-ethoxycarbonylaminoquinoline-5-carbonitrile
STUDIES ON AROMATIC NITRO COMPOUNDS. II. REACTION OF 2-NITRONAPHTHALENE WITH MALONONITRILE IN THE PRESENCE OF BASES
Ohshima, Toshihiko,Tomioka, Yukihiko,Yamazaki, Motoyoshi
, p. 1292 - 1298 (2007/10/02)
Treatment of 2-nitronaphthalene with malononitrile and potassium hydroxide gave the potassium salt (II) of 1,1-dicyano-2-hydroxy-2-(1-cyano-2-naphthylamino)ethylene (II') in 78percent yield.II was hydrolyzed to 2-aminonaphthalene via 3-dicyanomethylene-3,4-dihydro-1H-naphthoxazin-1-one (III) when heated with 20percent hydrochloric acid.III reacted with amines to form benzoquinazolines (IVa-d).II was treated with hydrochloric acid in pyridine to yield the pyridinium salt (IIa) of II', and IIa was converted to II by treatment with potassium acetate.II was also synthesized from ethyl N-(1-cyano-2-naphthyl)carbamate, malononitrile and potassium amide.Keywords: 2-nitronaphthalene; malononitrile; 1,1-dicyano-2-hydroxy-2-(1-cyano-2-naphthylamino)ethylene; hydrolysis; potassium hydroxide; 2-substituted 1,3-dioxo-1,2,3,4-tetrahydrobenzoquinazolines; acylation; ethyl N-(1-cyano-2-naphthyl)-carbamate
