Microwave-assisted Piloty-Robinson synthesis of 3,4-disubstituted pyrroles

Benjamin C. Milgram, Katrine Eskildsen, Steven M. Richter, W. Robert Scheidt, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

67 Scopus citations

Abstract

(Chemical Equation Presented) The synthesis of N-acyl 3,4-disubstituted pyrroles can be accomplished directly from hydrazine and an aldehyde via a Piloty-Robinson pyrrole synthesis. The use of microwave radiation for the cyclization and pyrrole formation greatly reduces the time necessary for this process and facilitates moderate to good yields from hydrazine for the corresponding 3,4-disubstituted products (5-12). By simple hydrolysis, the free N-H pyrroles can be accessed after the Piloty-Robinson reaction and then used directly in the synthesis of octaethylporphyrin (H2OEP, 14) and octaethyltetraphenylporphyrin (H2OETPP, 15).

Original languageEnglish (US)
Pages (from-to)3941-3944
Number of pages4
JournalJournal of Organic Chemistry
Volume72
Issue number10
DOIs
StatePublished - May 11 2007

ASJC Scopus subject areas

  • Organic Chemistry

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