Copper-Catalyzed Cascade Cyclization of 2-Nitrochalcones with NH-Heterocycles

We developed a method for allowing cascade cyclization of 2-nitrochalcones with pyrazoles, imidazole, and indazole in the presence of CuI catalyst, DBU base, and THF solvent. The conditions were tolerant of an array of useful functionalities including ester, nitro, cyano, halogen groups. A mechanistic consideration was also provided, as H<sub>2</sub>O<sub>2</sub> was presumably a byproduct. Our method appears to be a rare example to directly prepare C3-heterocyclic unprotected indoles.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-11-19
DOI
https://doi.org/10.1021/acs.joc.4c01960
Citations
5
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
1.25

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article

Copper-Catalyzed Cascade Cyclization of 2-Nitrochalcones with NH-Heterocycles

Tung Thanh Nguyen, Thang M. Ly, Tan N. Huynh, Nam Phan et al.
5 citations
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
1.25
article

Copper-Catalyzed Cascade Cyclization of 2-Nitrochalcones with NH-Heterocycles

Tung Thanh Nguyen, Thang M. Ly, Tan N. Huynh, Nam Phan, Phuong Dinh
article en
5 citations

Abstract

We developed a method for allowing cascade cyclization of 2-nitrochalcones with pyrazoles, imidazole, and indazole in the presence of CuI catalyst, DBU base, and THF solvent. The conditions were tolerant of an array of useful functionalities including ester, nitro, cyano, halogen groups. A mechanistic consideration was also provided, as H<sub>2</sub>O<sub>2</sub> was presumably a byproduct. Our method appears to be a rare example to directly prepare C3-heterocyclic unprotected indoles.

The Journal of Organic ChemistryVol. 89(23)
Vietnam National University Ho Chi Minh City (VN), Ho Chi Minh City University of Technology (VN)
University of Science Ho Chi Minh City
Clean water and sanitation
Openalex Percentile: Top 22%
Catalytic C–H Functionalization Methods
1.25
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Copper-Catalyzed Cascade Cyclization of 2-Nitrochalcones with NH-Heterocycles — Tung Thanh Nguyen, Thang M. Ly, et al. · The Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS