Application of N-isocyaniminotriphenyl phosphorane for preparation of heterocyclic acrylate as a key constituent of many industrial and pharmaceutical compounds

Subject Areas : Polymer

Milad Bazaz Rastkar ¹ , Bita Mohtat ² , Gholam Bagheri Marandi ³ , Hoorieh Djahaniani ⁴

1 - Department of Chemistry, Karaj Branch, Islamic Azad University, Karaj, Iran
2 - Department of Chemistry, Karaj Branch, Islamic Azad University, Karaj, Iran
3 - Department of Chemistry, Karaj Branch, Islamic Azad University, Karaj, Iran
4 - Department of Chemistry, East Tehran Branch, Islamic Azad University, Tehran, Iran

Received: 2022-12-06 Accepted : 2022-12-06 Published : 2023-01-01

Keywords:

Abstract :

2-Hydroxy pyridine undergoes a smooth reaction with electron-deficient acetylenic esters in thepresence of N-isocyaniminotriphenyl phosphorane under reflux conditions to produce theheterocyclic acrylate compounds in high yields. The acrylate structures with E/Z isomers wereobtained when the reaction was performed with 4-Hydroxy pyridine and 4-Hydroxy quinazoline,the acrylate structures with E/Z isomers were obtained. All compounds have many applications inmedicinal and industrial chemistry—configuration of E/Z isomers distinguished with nuclearmagnetic resonance technique and chemical shift of olefinic proton. The method offers a simple andefficient route for preparing acrylate heterocyclic compared to the other methodologies. Thestructures of the products were deduced and supported by 1HNMR and IR spectroscopy.

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