Selective one-pot synthesis of substituted pyrrole-3-phosphonates from alpha-cyanomethyl-beta-ketoesters

Date

2007-05-07

Author

Demir, Ayhan Sıtkı
Tural, Servet

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A one-step synthesis of 5-alkoxypyrrole-3-phosphonates is presented starting from suitable alpha-cyanomethyl-beta-ketophosphonates. The key step in the synthesis involves a one-pot addition and heteroannulation sequence. The zinc perchlorate-catalyzed addition of alcohols to the nitrile carbon of alpha-cyanomethyl- beta-ketophosphonates followed by annulation furnished 5-alkoxypyrrole-3-phosphonates. The addition-annulation process is carried out in the presence of water and 4,5-dihydro-5-oxo-1H-pyrrole-3-phosphonates (pyrrolinones) are obtained in good yields.

Subject Keywords

Organic Chemistry, Biochemistry, Drug Discovery

URI

https://hdl.handle.net/11511/56468

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/j.tet.2007.02.097

Collections

Department of Chemistry, Article

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Citation Formats

A. S. Demir and S. Tural, “Selective one-pot synthesis of substituted pyrrole-3-phosphonates from alpha-cyanomethyl-beta-ketoesters,” TETRAHEDRON, pp. 4156–4161, 2007, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56468.