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Original Articles

GLYCEROL CONDENSATION PRODUCTS OF AMINOANTHRAQUINONES

, , , , , & show all
Pages 121-144 | Received 12 Aug 2005, Accepted 16 Jan 2006, Published online: 16 Aug 2006
 

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.

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

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