Studies on Aromatic Nitro Compounds. III. Reaction of 2-Nitronaphthalene and 6-Nitroquinoline with Malononitrile in the Presence of Amine

Abstract

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 43% 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-tetrahydrobenzo [f] quinazoline (VIIId) were obtained in yields of 25 and 24%, respectively. On the other hand, the reaction of I with benzylamine gave only the quinazoline 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.