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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
