Synthesis of pyrrolo-pyrrolo-pyrazines via the Pd/C-catalyzed cyclization of N-propargyl pyrrolinyl-pyrrole derivatives

Date

2019-01-31

Author

Aslanoglu, Furgan
Basceken, Sinan
Balcı, Metin

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A novel and efficient synthesis of N-substituted dipyrrolo[1,2-a:2',1'-c]pyrazine derivatives has been developed. The synthetic strategy relies on the synthesis of 4',5'-dihydro-1H,3'H-2,2'-bipyrrole, followed by the reaction with propargyl bromide. Various substituents were introduced to the alkyne functionality using the Sonogashira coupling reaction. Aromatization of the dihydropyrrole ring followed by an intramolecular cyclization reaction between the alkyne functionality and the pyrrole nitrogen atom was catalyzed by Pd/C at high temperature to furnish the desired dipyrrolo-pyrazine skeleton.

Subject Keywords

Organic Chemistry, Biochemistry, Drug Discovery

URI

https://hdl.handle.net/11511/49322

Journal

TETRAHEDRON LETTERS

DOI

https://doi.org/10.1016/j.tetlet.2019.01.004

Collections

Graduate School of Natural and Applied Sciences, Article

Citation Formats

F. Aslanoglu, S. Basceken, and M. Balcı, “Synthesis of pyrrolo-pyrrolo-pyrazines via the Pd/C-catalyzed cyclization of N-propargyl pyrrolinyl-pyrrole derivatives,” TETRAHEDRON LETTERS, vol. 60, no. 5, pp. 449–451, 2019, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/49322.