Abstract
An unexpected product, 1-[(2-oxonaphthalen-1(2H)-ylidene)methyl]urea 4 of the condensation reaction of 2-hydroxy-1-naphthaldehyde with or without ethyl benzoylacetate and urea under hydrochloric acid-catalyzed and solvent-free conditions is reported.
Highlights
Dihydropyrimidinones (DHPMs) have attracted considerable interest due to the promising biological and pharmacological properties as calcium channel blockers, antihypertensive agents, and anticancer drugs associated with this heterocyclic scaffold.[1,2]
The synthesis of such a heterocyclic nucleus is of considerable importance, and quite a number of synthetic modifications based on the Biginelli three-component condensation reaction of aldehyde, β-ketoester, and urea have been developed.[3]
In continuation of our green chemistry programme towards the synthesis of DHPM heterocyclic compounds, we found an unexpected product, namely 1-[(2-oxonaphthalen-1(2H)-ylidene)methyl]urea 4 of the Biginelli reaction of 2-hydroxy-1-naphthaldehyde with ethyl benzoylacetate and urea under hydrochloric acid-catalyzed and solvent-free conditions (Scheme 1)
Summary
Dihydropyrimidinones (DHPMs) have attracted considerable interest due to the promising biological and pharmacological properties as calcium channel blockers, antihypertensive agents, and anticancer drugs associated with this heterocyclic scaffold.[1,2] the synthesis of such a heterocyclic nucleus is of considerable importance, and quite a number of synthetic modifications based on the Biginelli three-component condensation reaction of aldehyde, β-ketoester, and urea have been developed.[3]. In continuation of our green chemistry programme towards the synthesis of DHPM heterocyclic compounds, we found an unexpected product, namely 1-[(2-oxonaphthalen-1(2H)-ylidene)methyl]urea 4 of the Biginelli reaction of 2-hydroxy-1-naphthaldehyde with ethyl benzoylacetate and urea under hydrochloric acid-catalyzed and solvent-free conditions (Scheme 1).
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