79894-45-4Relevant academic research and scientific papers
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
