An Efficient Synthesis and Reactions of Novel Indolyl- pyridazinone Derivatives with Expected Biological Activity

摘要

Reaction of 4-anthracen-9-yl-4-oxo-but-2-enoic acid (>1) with indole gave the corresponding butanoic acid >2. Cyclocondensation of >2 with hydrazine hydrate, phenyl hydrazine, semicarbazide and thiosemicarbazide gave the pyridazinone derivatives >3a-d. Reaction of >3a with POCl3 for 30 min gave the chloropyridazine derivative >4a, which was used to prepare the corresponding carbohydrate hydrazone derivatives >5a-d. Reaction of chloropyridazine >4a with some aliphatic or aromatic amines and anthranilic acid gave >6a-f and >7, respectively. When the reaction of the pyridazinone derivative >3a with POCl3 was carried out for 3 hr an unexpected product 4b was obtained. The structure of >4b was confirmed by its reaction with hydrazine hydrate to give hydrazopyridazine derivative >9, which reacted in turn with acetyl acetone to afford >10. Reaction of >4b with methylamine gave >11, which reacted with methyl iodide to give the trimethylammonium iodide derivative >12. The pyridazinone >3a also reacted with benzene- or 4-toluenesulphonyl chloride to give >13a-b and with aliphatic or aromatic aldehydes to give >14a-g. All proposed structures were supported by IR, ¹H-NMR, ¹³C-NMR, and MS spectroscopic data. Some of the new products showed antibacterial activity.