Abstract
A green and efficient method for the preparation of 5-aryl-4-hydroxy-2-methyl-1H-pyrrole-3carboxylic acid esters and 6-aryl-3-methylpyridazine-4-carboxylic acid esters via threecomponent reaction of arylglyoxal hydrates with β-dicarbonyl compounds in the presence of ammonium acetate and hydrazine hydrate using water as solvent under ultrasonic irradiation was reported. The reactions proceeded rapidly and afforded the corresponding pyrroles and pyridazines in good to high yields in very short reaction time.
Highlights
Condensation reactions of arylglyoxals, aromatic α-keto aldehydes, containing both aldehyde and ketone functional groups with different reactivity, play an important role in organic synthesis especially in synthesis of heterocyclic compounds[1]
Many methods have been developed for pyrrole synthesis[6], which include Knorr, Paal-Knorr, and Hantzsch syntheses and 1,3-dipolar cycloaddition reactions
Despite the large number of reports on the construction of pyrrole and pyridazine heterocycles are available in the literature, due to the importance of these heterocycles in medicinal and material chemistry, development of new routes, which lead to these heterocycles in higher yields, shorter reaction time or milder conditions could receive considerable attention in organic synthesis
Summary
Condensation reactions of arylglyoxals, aromatic α-keto aldehydes, containing both aldehyde and ketone functional groups with different reactivity, play an important role in organic synthesis especially in synthesis of heterocyclic compounds[1]. A large number of organic reactions[14] and synthesis of pyrroles and pyridazines[15] were reported under ultrasound (US) irradiation.
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