Work

Microwave-Assisted Piloty−Robinson Synthesis of 3,4-Disubstituted Pyrroles

Year: 2007

Type: article

Abstract: 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).

Source: The Journal of Organic Chemistry

DOI: 10.1021/jo070389+

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

Institutions: University of Notre Dame, Northwestern University

Language: English

Topic: Synthesis and Characterization of Pyrroles

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Amgen, National Institutes of Health, National Institute of General Medical Sciences, Division of Chemistry

Awards: G387268629, G4170873571