Modular Synthesis of 3,4‐Disubstituted Pyrroles Through Three‐Component Van Leusen Reaction of Propargylamines with Tosylmethyl Isocyanide and Water

A novel three‐component van Leusen strategy has been developed for the efficient and straightforward synthesis of valuable 3,4‐disubstituted pyrroles from easily available propargylamines, tosylmethyl isocyanide, and water. This transformation advances through the formation of a pyrrole framework via [3 + 2] cycloaddition with tosylmethyl isocyanide and a sequential nucleophilic substitution, ring‐opening, and deprotonation/protonation cascade process. This reaction provides a convenient modular access to pyrrole derivatives with aryl and benzoyl groups through the formation of three new bonds and one heterocycle from readily available acyclic precursors in a single step.

Authors

Institutions

Publication Details

Journal
European Journal of Organic Chemistry
Published
2025-10-08
DOI
https://doi.org/10.1002/ejoc.202500855
Primary Topic
Synthesis and Characterization of Pyrroles
Type
article
Field-Weighted Citation Impact
0.00
Controls
|||
ALL TIME
JAN
FEB
MAR
APR
MAY
JUN
JUL
AUG
SEP
OCT
article

Modular Synthesis of 3,4‐Disubstituted Pyrroles Through Three‐Component Van Leusen Reaction of Propargylamines with Tosylmethyl Isocyanide and Water

Binbin Fei, Qiang Tang, Xinwei He, Yongjia Shang et al.
European Journal of Organic Chemistry
Synthesis and Characterization of Pyrroles
article

Modular Synthesis of 3,4‐Disubstituted Pyrroles Through Three‐Component Van Leusen Reaction of Propargylamines with Tosylmethyl Isocyanide and Water

Binbin Fei, Qiang Tang, Xinwei He, Yongjia Shang, Yanan Liu, Yangzilin Kong, Na Gu
article en

Abstract

A novel three‐component van Leusen strategy has been developed for the efficient and straightforward synthesis of valuable 3,4‐disubstituted pyrroles from easily available propargylamines, tosylmethyl isocyanide, and water. This transformation advances through the formation of a pyrrole framework via [3 + 2] cycloaddition with tosylmethyl isocyanide and a sequential nucleophilic substitution, ring‐opening, and deprotonation/protonation cascade process. This reaction provides a convenient modular access to pyrrole derivatives with aryl and benzoyl groups through the formation of three new bonds and one heterocycle from readily available acyclic precursors in a single step.

European Journal of Organic ChemistryVol. 28(45)
Wannan Medical College (CN), First Affiliated Hospital of Wannan Medical College (CN), Anhui Normal University (CN)
Openalex Percentile: Top 78%
Synthesis and Characterization of Pyrroles
AI Navigator

Ask Laika to Summarize, Analyze, and Connect papers live on the map.

Summarize Papers & Methodologies

Extract key findings, datasets, and comparative methods across publications.

Benchmark Rankings & Visual Analytics

Rank top research institutions, authors, funders, topics, and journals by Field-Weighted Citation Impact (FWCI) and paper volume with instant charts.

Connect Distant Disciplines

Bridge topological clusters on the map to find hidden collaborative intersections.