QD77 : Synthesis of new derivatives triazolo and pyrrolo quinoxaline by Palladium catalyst
Thesis > Central Library of Shahrood University > Chemistry > MSc > 2011
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Abstarct: The Pyrrolo and triazoloquinoxalines are present in many pharmaceutical agents which exhibit a broad spectrum of biological activities such as antiviral, and anticancer properties.
In this work efficent synthesis of derivatives of 2-phenyl-N-arylmethylene-1-H- pyrrolo[2,3-b]quinoxaline-1-amine (90 a-k) and 1-aryl-4-(phenylethynyl) [1,2,4]triazolo[4,3-a]quinoxaline (91 a-f) through Pd/C catalyzed heteroannulation has been reported. When compounds 2,3-dichloroquinoxaline (39) hydrazine (87) and varius aromatic aldehydes (88) was treated with phenylacetylene in water in the presence of Pd/C, cuprous iodide and potassiumcarbonate at 70¼C, under argon atmosphere, new derivatives of 2-phenyl-N-arylmethylene-1-H- pyrrolo[2,3-b]quinoxaline-1-amine (90 a-k). were obtained in good to high yields and when compounds 2,3-dichloroquinoxaline (39), hydrazine (87), varius aromatic aldehydes (88) and bromine (43) was treated with phenylacetylene in water in the presence of Pd/C and potassiumcarbonate at 70¼C, under argon atmosphere, new derivatives of 1-aryl-4-(phenylethynyl) [1,2,4]triazolo[4,3-a]quinoxaline (91 a-f) were obtained in good to high yields.
The structure of products were stablished from spectroscopic data obtained. In conclusion, the described method for the synthesis of 2-phenyl-N-arylmethylene-1-H- pyrrolo[2,3-b]quinoxaline-1-amine (90 a-k) and 1-aryl-4-(phenylethynyl) [1,2,4]triazolo[4,3-a]quinoxaline (91 a-f) are easy and one-pot procedures which lead to high yields of product, and can be extended to the synthesis of other heterocyclic compounds.
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