Selective synthesis of N-substituted pyrrolo[1,2-a]pyrazin-1(2H)-one derivatives via alkyne cyclization

Date

2014-12-03

Author

Cetinkaya, Yasin
Balcı, Metin

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A novel and efficient synthesis of N-substituted pyrrolo-pyrazinone derivatives has been developed. A trichloroacetyl group connected to the pyrrole ring was converted into the desired carboxamide derivatives. Promoted by NaH, the pyrrole carboxamide derivatives underwent a tandem reaction with propargyl bromide to afford pyrrolo-pyrazinones with high efficiency under very mild conditions. The mechanism for the formation of the products is discussed and supported by DFT calculations. (C) 2014 Elsevier Ltd. All rights reserved

Subject Keywords

Pyrrole, Pyrazine, Pyrazinone, Pyrrolopyrazinone, Alkyne cyclization

URI

https://hdl.handle.net/11511/52338

Journal

TETRAHEDRON LETTERS

DOI

https://doi.org/10.1016/j.tetlet.2014.10.044

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

Y. Cetinkaya and M. Balcı, “Selective synthesis of N-substituted pyrrolo[1,2-a]pyrazin-1(2H)-one derivatives via alkyne cyclization,” TETRAHEDRON LETTERS, pp. 6698–6702, 2014, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/52338.