Streamlined One‐Pot Synthesis of Fused Pyrroles: A Three‐Component Approach

New modified pyrrole derivatives, namely tetrahydroindol-4-ones and pyrrolo[2,3-d]pyrimidines, functionalized at position 3, were synthesized through a one-pot multicomponent condensation. Stabilized dimedone enaminones derived from α-amino acids and their esters (or 6-amino-1,3-dimethyluracil), arylglyoxals, and methylene-active compounds (malononitrile, Meldrum's acid) were selected as key reagents for the reaction. Functionalization of 3-cyanoacetamides within the 4,5,6,7-tetrahydroindol-4-one framework was performed, involving transformations of the cyanoamide fragment, carbonyl group, and acetate residue at position 1 of the bicyclic system. The reactions proceeded under mild conditions, without the use of hazardous organic solvents or catalysts. Multicomponent condensation approach is particularly attractive for such syntheses, as it offers high atom economy, operational efficiency, and enables the rapid construction of structurally diverse and complex molecules in a single synthetic operation, thereby affording good yields with straightforward purification.

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Publication Details

Journal
ChemistryOpen
Published
2026-03-26
DOI
https://doi.org/10.1002/open.70181
Primary Topic
Synthesis and Characterization of Pyrroles
Type
article
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article

Streamlined One‐Pot Synthesis of Fused Pyrroles: A Three‐Component Approach

Nadiia N. Kolos, Henning J. Jessen, Oleksandr S. Kharchenko, Kateryna I. Marchenko et al.
ChemistryOpen
Synthesis and Characterization of Pyrroles
article

Streamlined One‐Pot Synthesis of Fused Pyrroles: A Three‐Component Approach

Nadiia N. Kolos, Henning J. Jessen, Oleksandr S. Kharchenko, Kateryna I. Marchenko, Roman M. Gutzul, Vladislava I. Grinko
article en

Abstract

New modified pyrrole derivatives, namely tetrahydroindol-4-ones and pyrrolo[2,3-d]pyrimidines, functionalized at position 3, were synthesized through a one-pot multicomponent condensation. Stabilized dimedone enaminones derived from α-amino acids and their esters (or 6-amino-1,3-dimethyluracil), arylglyoxals, and methylene-active compounds (malononitrile, Meldrum's acid) were selected as key reagents for the reaction. Functionalization of 3-cyanoacetamides within the 4,5,6,7-tetrahydroindol-4-one framework was performed, involving transformations of the cyanoamide fragment, carbonyl group, and acetate residue at position 1 of the bicyclic system. The reactions proceeded under mild conditions, without the use of hazardous organic solvents or catalysts. Multicomponent condensation approach is particularly attractive for such syntheses, as it offers high atom economy, operational efficiency, and enables the rapid construction of structurally diverse and complex molecules in a single synthetic operation, thereby affording good yields with straightforward purification.

ChemistryOpenVol. 15(4)
University of Freiburg (DE), University of Education Freiburg (DE), Enamine (Ukraine) (UA), V. N. Karazin Kharkiv National University (UA)
Industry, innovation and infrastructure
Openalex Percentile: Top 7%
Synthesis and Characterization of Pyrroles
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