QD56 : Synthesis of new derivatives of pyrrolo[2,3-b]quinoxaline-2- carbaldehydes by Pd-Cu catalyst
Thesis > Central Library of Shahrood University > Chemistry > MSc > 2009
Authors:
Amin Rahimi [Author], Ali Keivanloo[Supervisor], Mohammad Bakherad[Supervisor]
Abstarct: The quinoxaline nucleus is present in many pharmaceutical agents exhibiting a broad spectrum of biological activities such as antiviral, antiglucoma, and anticancer activities. In this work efficent synthesis of pyrroloquinoxalines through palladium – catalyzed heteroannulation is reported. The reaction of 2,3-dichloroquinoxaline (15) with varius primarty alkylamines in refluxing acetonitril affordes 2-alkylamino-3-chloroquinoxalines (109 a-f ) in high yield. When compounds (109 a-f) was treated with 3-bromo-1-propyne and morpholine in the presence of bis(triphenylphosphine)palladium chloride and cuprous iodide at 70 ºC, new drivatives of 1-alkyl-1H-pyrrolo[2,3-b]quinoxaline-2-carbaldehydes (110 a-f) were obtained in good to high yields. The reaction was carried out in morpholine as solvent, and baxse under an argon atmosphere. In the proposed mechanism for this reaction, the Pd(0) is formed in situ from the added catalyst. The structure of products were stablished by spectroscopic data. In conclusion the described method for the synthesis of N-substituted pyrroloquinoxaline-2-carbaldehydes is an easy and one-pote procedure with good to high yields which can be extended to the synthesis of other heterocyclic compounds.
Keywords:
#- Link
Keeping place: Central Library of Shahrood University
Visitor: