Selective one-pot synthesis of substituted pyrrole-3-phosphonates from α-cyanomethyl-β-ketoesters |
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Authors: | Ayhan S. Demir Servet Tural |
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Affiliation: | a Department of Chemistry, Middle East Technical University, 06531 Ankara, Turkey b Department of Chemistry, Dicle University, 21280 Diyarbakir, Turkey |
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Abstract: | A one-step synthesis of 5-alkoxypyrrole-3-phosphonates is presented starting from suitable α-cyanomethyl-β-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 α-cyanomethyl-β-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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Keywords: | Pyrroles Heteroannulation GABA analogs β-Ketophosphonates Pyrrolinones |
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