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Issue 9, 2021
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Ring-contraction of hantzsch esters and their derivatives to pyrroles via electrochemical extrusion of ethyl acetate out of aromatic rings

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Abstract

Electrochemical ring-contraction of HEs and theirs pyridine derivatives is developed to obtain polysubstituted pyrroles. This process provides an orthogonal utilization of Hantzsch esters for the well-documented application as side chain or hydrogen donors. The formal transformation shows an extrusion of ethyl acetate out of the pyridine ring in a single step. In addition to the novel transformation, we also discovered the Lewis acid's intermolecular control of regioselectivity during an intramolecular electrochemical process. The reaction provides a number of polysubstituted pyrroles that have never been accessed, including pharmaceutical intermediates and photoswitches. An unusual 4-electron continuous reduction drives the unprecedented anionic dearomatization/ring-contraction/rearomatization pathway.

Graphical abstract: Ring-contraction of hantzsch esters and their derivatives to pyrroles via electrochemical extrusion of ethyl acetate out of aromatic rings

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Supplementary files

Article information


Submitted
07 Feb 2021
Accepted
08 Apr 2021
First published
08 Apr 2021

Green Chem., 2021,23, 3468-3473
Article type
Paper

Ring-contraction of hantzsch esters and their derivatives to pyrroles via electrochemical extrusion of ethyl acetate out of aromatic rings

X. Liu, C. Liu and X. Cheng, Green Chem., 2021, 23, 3468
DOI: 10.1039/D1GC00487E

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