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

Demir, Ayhan Sıtkı
Tural, Servet
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.


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A novel synthesis of 1,2,4-oxadiazoles and isoxazoles is described by utilizing the reactions between amidoximes and alpha,beta-alkynic aldehydes and/or ketones. Conjugate addition products, obtained from amidoximes and alpha,beta-alkynic aldehydes and/or ketones, afford 1,2,4-oxadiazoles and isoxazoles when treated with bases and acids, respectively. 1,2,4-Oxadiazoles can also be synthesized directly from amidoximes and alpha,beta-alkynic aldehydes in a one-pot manner under basic conditions. The reactions ...
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: