Work

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

Year: 2020

Type: article

Abstract: 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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.0c01263

Authors: Susanna K. Maisto, Angela P. Leersnyder, Gwyneth L. Pudner, Jonathan R. Scheerer

Institution: William & Mary

Language: English

Topic: Synthesis and Characterization of Pyrroles

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: College of William and Mary, National Institute of General Medical Sciences

Award: New methods to prepare 1,4-oxazin-2-ones and applications in the construction of polysubstituted pyridines