Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on Aromatic Nitro Compounds. II. Reaction of 2-Nitronaphthalene with Malononitrile in the Presence of Bases
TOSHIHIKO OHSHIMAYUKIHIKO TOMIOKAMOTOYOSHI YAMAZAKI
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1981 Volume 29 Issue 5 Pages 1292-1298

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Abstract
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 78% yield. II was hydrolyzed to 2-aminonaphthalene via 3-dicyanomethylene-3, 4-dihydro-1H-naphth [2, 1-d] [1, 3] oxazin-1-one (III) when heated with 20% hydrochloric acid. III reacted with amines to form benzo [f] quinazolines (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.
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© The Pharmaceutical Society of Japan
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