Synthesis of 3,4-Fused Pyrroles with Seven-Membered Carbocycles via Cascade C–C σ-Bond Cleavage/Intramolecular Cyclization Reactions

A novel tandem reaction involving amino-substituted ynones and cyclic carbonyls has been developed, efficiently synthesizing 3,4-fused pyrroles with seven-membered carbocycles by a one-pot method. This reaction proceeds through a cascade ring-expansion of cyclic carbonyls, followed by intramolecular cyclization reactions. This metal-free strategy enables the concurrent construction of the medium-sized ring and the pyrrole ring, exhibiting a high step economy.

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Publication Details

Journal
Organic Letters
Published
2025-05-23
DOI
https://doi.org/10.1021/acs.orglett.5c01607
Citations
1
Primary Topic
Advanced Synthetic Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.94

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article

Synthesis of 3,4-Fused Pyrroles with Seven-Membered Carbocycles via Cascade C–C σ-Bond Cleavage/Intramolecular Cyclization Reactions

Qiongwen Kang, Zongkang Wang, Peng He, Nana Fei et al.
1 citations
Organic Letters
Advanced Synthetic Organic Chemistry
0.94
article

Synthesis of 3,4-Fused Pyrroles with Seven-Membered Carbocycles via Cascade C–C σ-Bond Cleavage/Intramolecular Cyclization Reactions

Qiongwen Kang, Zongkang Wang, Peng He, Nana Fei, Yanjun Wang, Yanzhong Li, Lingkai Kong
article en
1 citations

Abstract

A novel tandem reaction involving amino-substituted ynones and cyclic carbonyls has been developed, efficiently synthesizing 3,4-fused pyrroles with seven-membered carbocycles by a one-pot method. This reaction proceeds through a cascade ring-expansion of cyclic carbonyls, followed by intramolecular cyclization reactions. This metal-free strategy enables the concurrent construction of the medium-sized ring and the pyrrole ring, exhibiting a high step economy.

Organic LettersVol. 27(22)
Linyi University (CN), East China Normal University (CN)
National Natural Science Foundation of China
Zero hunger
Openalex Percentile: Top 26%
Advanced Synthetic Organic Chemistry
0.94
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