GLYCEROL CONDENSATION PRODUCTS OF AMINOANTHRAQUINONES

Glycerol condensation reaction of 2- and 1-aminoanthraquinones was reexamined. 2-Aminoanthraquinone gave phenaleno[3,2-f]quinolin-7-one (10,11-pyridinobenzanthrone), 9H- phenanthro[10,1-gh]quinolin-9-one (4,5-pyridinobenzanthrone) and phenaleno[2,3-g]quinolin-7-one (10,9-pyridinobenzanthrone) besides phenaleno[2,3-f]quinolin-13-one (9,8-pyridinobenzanthrone) hitherto reported. 1-Aminoanthraquinone gave phenaleno[3,2-h]quinolin-13-one (8,9-pyridinobenzanthrone) along with a small amount of phenaleno[2,3-h]quinolin-7-one (11,10-pyridinobenzanthrone), but not 13H-phenanthro[1,10-gh]quinolin-13-one (6,5-pyridinobenzanthrone) as hitherto reported. NMR spectra of these six compounds were assigned and they supported the assigned isomeric structures.

Keywords:

• Pyridinobenzanthrone
• phenalenoquinoline
• phenanthroquinoline
• glycerol condensation product of aminoanthraquinone
• NMR spectra of pyridinobenzanthrone

The authors thank very much our referees for their kind comments and keen suggestions about the reaction mechanism.