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Synthesis of N‐Substituted Pyrrole‐2,5‐Dicarboxylic Acids from d‐Galactaric Acid

Authors: Jan‐Simon Jeshua Friedrichs; Kai Stirnweiß; Corinna Urmann; Volker Sieber;

Synthesis of N‐Substituted Pyrrole‐2,5‐Dicarboxylic Acids from d‐Galactaric Acid

Abstract

Pyrrole‐2,5‐dicarboxylic acid (PDCA) and its N‐substituted derivatives are interesting building blocks for macromolecular applications. However, only a few published procedures describe the synthesis of PDCA derivatives. These procedures often suffer from low yields, the formation of unwanted side products, harsh reaction conditions, the use of toxic and expensive reagents, or the unavailability of certain derivatives. Here, a facile and scalable six‐step synthetic route is described, starting from biobased d‐galactaric acid, for the production of N‐alkylated and N‐arylated PDCAs, achieving total yields of up to 45%. In addition, the E‐factor of the presented synthesis route is decreased by a factor of 14 compared to already established methods.

Keywords

2100 Energy, 1500 Chemical Engineering, 2500 Materials Science, Elimination, Methanol, Dbu, Pyrrole, Waste, 2304 Environmental Chemistry, Oxidation, Reagent, Challenges, Mucic Acid, Peptides, Research Article

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    popularity
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    Top 10%
    influence
    This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
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    impulse
    This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
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selected citations
These citations are derived from selected sources.
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
2
Top 10%
Average
Average
Green
hybrid