Tropone Hydrazides in [10+2]‐Hetero‐Higher‐Order Cycloaddition for the Synthesis of Tetrahydropyridazine Derivatives

Abstract [10+2]‐Hetero‐higher‐order cycloaddition between tropone hydrazides (acting as 10π‐components) and 3‐alkylidene oxindoles (acting as 2π‐components) has been established. Under Brønsted base catalysis the reaction proceeded in a fully peri‐ and diastereoselective manner with the stereochemical outcome governed mainly by electronic interactions. Following such a strategy, a series of structurally diverse tetrahydropyridazines were prepared in 30–70% yields. Furthermore, the potential of the obtained cycloadducts has been confirmed in selected chemoselective transformations.

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Publication Details

Journal
Advanced Synthesis & Catalysis
Published
2024-10-08
DOI
https://doi.org/10.1002/adsc.202401033
Citations
2
Primary Topic
Oxidative Organic Chemistry Reactions
Type
article
Field-Weighted Citation Impact
0.50

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article

Tropone Hydrazides in [10+2]‐Hetero‐Higher‐Order Cycloaddition for the Synthesis of Tetrahydropyridazine Derivatives

Adam Cieśliński, Łukasz Albrecht, Anna Skrzyńska, Lesław Sieroń et al.
2 citations
Advanced Synthesis & Catalysis
Oxidative Organic Chemistry Reactions
0.50
article

Tropone Hydrazides in [10+2]‐Hetero‐Higher‐Order Cycloaddition for the Synthesis of Tetrahydropyridazine Derivatives

Adam Cieśliński, Łukasz Albrecht, Anna Skrzyńska, Lesław Sieroń, Artur Przydacz
article en
2 citations

Abstract

Abstract [10+2]‐Hetero‐higher‐order cycloaddition between tropone hydrazides (acting as 10π‐components) and 3‐alkylidene oxindoles (acting as 2π‐components) has been established. Under Brønsted base catalysis the reaction proceeded in a fully peri‐ and diastereoselective manner with the stereochemical outcome governed mainly by electronic interactions. Following such a strategy, a series of structurally diverse tetrahydropyridazines were prepared in 30–70% yields. Furthermore, the potential of the obtained cycloadducts has been confirmed in selected chemoselective transformations.

Advanced Synthesis & CatalysisVol. 367(3)
Lodz University of Technology (PL), Institute of Organic Chemistry (PL)
Narodowe Centrum Nauki
Clean water and sanitation
Openalex Percentile: Top 39%
Oxidative Organic Chemistry Reactions
0.50
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