New approaches to polysubstituted pyrroles and pyrrolinones from alpha-cyanomethyl-beta-ketoesters

Date

2007-01-08

Author

Demir, Ayhan Sıtkı
Emrullahoglu, Mustafa
Ardahan, Gulben

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In this present paper, we report the efficient, regioselective one-pot synthesis of 5-alkoxy and 5-alkylsulfanylpyrrole-3-carboxylates in high yields via the zinc perchlorate-catalyzed addition of alcohols and thiols to the nitrile carbon of alpha-cyanornethyl-beta-ketoesters followed by annulation. The addition-annulation process is undertaken in aqueous solution to give 4,5-dihydro-5-oxo-1H-pyrrole-beta-carboxylates (pyrrolinones) in good yields. These 4,5-dihydro-5-oxo-1H-pyrrole-3-carboxylates are also obtained by the hydrolysis of 5-alkoxypyrrole-3-carboxylates.

Subject Keywords

Organic Chemistry, Biochemistry, Drug Discovery

URI

https://hdl.handle.net/11511/57821

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/j.tet.2006.10.054

Collections

Department of Chemistry, Article

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Citation Formats

A. S. Demir, M. Emrullahoglu, and G. Ardahan, “New approaches to polysubstituted pyrroles and pyrrolinones from alpha-cyanomethyl-beta-ketoesters,” TETRAHEDRON, pp. 461–468, 2007, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57821.