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Synthesis of Pyrrolopyrazinones by Construction of the Pyrrole Ring onto an Intact Diketopiperazine. | LitMetric
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Synthesis of Pyrrolopyrazinones by Construction of the Pyrrole Ring onto an Intact Diketopiperazine.

Susanna K Maisto Angela P Leersnyder Gwyneth L Pudner Jonathan R Scheerer

J Org Chem

Department of Chemistry, The College of William & Mary, P.O. Box 8795, Williamsburg, Virginia 23187, United States.

Published: July 2020

This study reveals an alternative sequence for the synthesis of compounds that contain the pyrrolodiketopiperazine structural motif. Starting with a diketopiperazine precursor, a mild aldol condensation precedes pyrrole annulation and bicyclic ring fusion. The derived intermediate aldol condensation products, which bear either a protected carbonyl or a functionalized alkyne, can be cyclized to the pyrrolodiketopiperazine by protic or gold Lewis acid catalysis.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7464856PMC
http://dx.doi.org/10.1021/acs.joc.0c01263DOI Listing

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