Nashrieh Shimi va Mohandesi Shimi Iran

Nashrieh Shimi va Mohandesi Shimi Iran

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

Document Type : Research Article

Authors
Milad Bazaz Rastkar
Bita Mohtat
Chemistry Department, Karaj Branch, Islamic Azad University, Karaj, I.R. IRAN
Abstract
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.
Keywords
4-Hydroxyquinazoline؛ 2-Hydroxypyridine؛ 2-Hydroxyquinoline
4-Hydroxyquinazoline isoquinoline؛ Dialkyl acetylene dicarboxylates؛ Acrylate heterocyclic derivatives؛ Multicomponent reaction
Subjects
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