Sythesis of Dialkyl 2-(4-oxoquinazolin-3(4H)-yl) acrylates via two Component Reaction of 4-Hydroxyquinazoline with Dialkyl acetylene dicarboxylate in the Presence of Isoquinoline
4-Hydroxyquinazoline undergoes a smooth reaction with dialkyl acetylene dicarboxylates in the presence of isoquinoline and dichloromethane (CH2Cl2) as a solvent to produce the E/Z isomers of acrylate heterocyclic derivatives. The structures of (Z)- and (E)- isomers were deduced from infrared (IR), nuclear magnetic resonance (1H NMR, and 13C NMR) and mass spectroscopy. Proton magnetic resonance spectroscopy (H NMR) was employed to distinguish between (Z)- and (E)- configurations of the carbon-carbon double bonds is based on the chemical shift of the olefinic proton when the reaction was performed by 2-Hydroxypyridine, 2-Hydroxyquinoline and 4-Hydroxypyridine, the same E/Z of heterocyclic dialkyl acrylates were obtained. In this research, a simple and mild method to access acrylate heterocyclic derivatives via a multi-component reaction is described.
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