NaH-Mediated One-Pot Cyclocondensation of 6-Nitroquinoline with Aromatic Hydrazones To Form [1.2.4]Triazino[6,5-<i>f</i>]quinolines and/or Pyrazolo[3,4-<i>f</i>]quinolines

Abstract

[reaction: see text] 6-Nitroquinoline undergoes direct cyclocondensation with aromatic hydrazones in the presence of sodium hydride in DMF at -10 degrees C, giving the corresponding 3-aryl-1(3)H-pyrazolo[3,4-f]quinolines and/or 3-aryl[1.2.4]triazino[6,5-f]quinolines in low to moderate yield. The mode of cyclocondensation is considerably dependent on the electronic nature of ring substituent of hydrazones, an electron-donating substituent favoring the formation of the latter heterocycles.