Cascade Cloke–Wilson Rearrangement of Enyne-Amides and 2-Bromomalonates to Construct 2,3-Furan-Fused Dihydropyrroles

Reported herein is a cascade Cloke-Wilson rearrangement of enyne amides with bromomalonates, enabling the efficient construction of 2,3-furan-fused dihydropyrrole derivatives in good yields. Moreover, this strategy can be extended to other azadiene derivatives, providing access to tetra-substituted dihydropyrroles in moderate to excellent yields (40-88%). The use of inexpensive and readily available starting materials, broad substrate scope, mild reaction conditions, and the versatile synthetic utility of the resulting dihydropyrroles render this protocol an attractive and practical synthetic methodology.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-05-21
DOI
https://doi.org/10.1021/acs.joc.6c00111
Primary Topic
Catalytic Alkyne Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Cascade Cloke–Wilson Rearrangement of Enyne-Amides and 2-Bromomalonates to Construct 2,3-Furan-Fused Dihydropyrroles

T T Wang, Mengwei You, Yongli Li, Zeyu Hu et al.
The Journal of Organic Chemistry
Catalytic Alkyne Reactions
article

Cascade Cloke–Wilson Rearrangement of Enyne-Amides and 2-Bromomalonates to Construct 2,3-Furan-Fused Dihydropyrroles

T T Wang, Mengwei You, Yongli Li, Zeyu Hu, Hui Mao, Fanbo Lei, Jia-Hong Wu, Liejin Zhou
article en

Abstract

Reported herein is a cascade Cloke-Wilson rearrangement of enyne amides with bromomalonates, enabling the efficient construction of 2,3-furan-fused dihydropyrrole derivatives in good yields. Moreover, this strategy can be extended to other azadiene derivatives, providing access to tetra-substituted dihydropyrroles in moderate to excellent yields (40-88%). The use of inexpensive and readily available starting materials, broad substrate scope, mild reaction conditions, and the versatile synthetic utility of the resulting dihydropyrroles render this protocol an attractive and practical synthetic methodology.

The Journal of Organic Chemistry
Sichuan University (CN), Ministry of Education (PT), Green Chemistry (PL), Jinhua University of Vocational Technology (CN), Pharmaceutical Biotechnology (Czechia) (CZ)
National Natural Science Foundation of China
Openalex Percentile: Top 10%
Catalytic Alkyne Reactions
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