Efficient Synthesis of Functionalized 2,5-Dihydropyrrole Derivatives by Ph₃P-Promoted Condensation between Acetylene Esters and α-Arylamino Ketones

Mohammad Anary-Abbasinejad*, Ehsanorreza Poorhassan, Alireza Hassanabadi

*Department of Chemistry, Islamic Azad University, Yazd Branch, PO Box 89195-155, Yazd, Iran, Email: mohammadanaryyahoo.com

M. Anary-Abbasinejad, E. Poorhassan, A. Hassanabadi, Synlett, 2009, 1929-1932.

DOI: 10.1055/s-0029-1217516

Abstract

A reaction between dialkyl acetylenedicarboxylates and β-aminoketones promoted by triphenylphosphine allows an efficient one-pot synthesis of polysubstituted 2,5-dihydropyrrole derivatives. The prepared 2,5-dihydropyrroles can be easily oxidized to the corresponding pyrrole derivatives with chromium trioxide.

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A Novel Approach to the Synthesis of Highly Functionalized Pyrroles

M. Anary-Abbasinejad, K. Charkhati, H. Anaraki-Ardakani, Synlett, 2009, 1115-1117.

Key Words

2,5-dihydropyrroles, pyrroles, dialkyl acetylenedicarboxylates, β-aminoketones, triphenylphosphine, intramolecular Wittig reaction, chromium trioxide

ID: J60-Y2009-2060

Efficient Synthesis of Functionalized 2,5-Dihydropyrrole Derivatives by Ph3P-Promoted Condensation between Acetylene Esters and α-Arylamino Ketones

Mohammad Anary-Abbasinejad*, Ehsanorreza Poorhassan, Alireza Hassanabadi

Efficient Synthesis of Functionalized 2,5-Dihydropyrrole Derivatives by Ph₃P-Promoted Condensation between Acetylene Esters and α-Arylamino Ketones