QD70 : Synthesis of substituted pyrrolo[2,3-b] quinoxalines in peresence of Pd catalyst
Thesis > Central Library of Shahrood University > Chemistry > MSc > 2010
Authors:
Samaneh baratnia [Author], Ali Keivanloo[Supervisor], Seyyed Ali naghi Taheri[Advisor]
Abstarct: The quinoxaline nucleus which is present in many pharmaceutical agents exhibite a broad spectrum of biological activities such as antiviral, antiglucoma, and anti-cancer. In this work an efficent synthesis of [2,3-b] pyrroloquinoxalines through palladium¬–¬catalyzed heteroannulation is reported. The reaction of 2,3-dichloroquinoxaline (85) with varius primary alkylamines in refluxing acetonitrile give rise to 2-alkylamino-3-chloroquinoxalines (82 a-g ) in high yields. When compounds (82 a-g) were treated with terminal alkynes in morpholine in the presence of bis(triphenylphosphine)palladium¬chloride and cuprous iodide at 70 ºC, new drivatives of 1-alkyl-2-phenyl(buthyl)-1H-pyrrolo[2,3-b]quinoxalines (84 a-h) were obtained in good to high yields. In this reaction which was carried out under an argon atmosphere, morpholine acted as both solvent and baxse. In the proposed mechanism for this reaction, the Pd(0) is formed in situ from added catalyst. The structure of the products were stablished from spectroscopic data. In conclusion, the described method for the synthesis of N-substituted pyrroloquinoxalines is an easy and one-pot procedure which affords the products with good to high yields, and can be extended to the synthesis of other heterocyclic compounds.
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