Selective one-pot synthesis of substituted pyrrole-3-phosphonates from α-cyanomethyl-β-ketoesters-Science-Chemical Encyclopedia-lookchem

Selective one-pot synthesis of substituted pyrrole-3-phosphonates from α-cyanomethyl-β-ketoesters
Add time:08/18/2019 Source:sciencedirect.com

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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