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NaH-mediated one-pot cyclocondensation of 6-nitroquinoline with aromatic hydrazones to form
1Department of Chemistry, School of Science, Kwansei Gakuin University, Nishinomiya, Japan.
Organic Letters
|May 18, 2000
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.