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.
Authors
- Adam Cieśliński (ORCID: https://orcid.org/0000-0003-4551-6492)
- Łukasz Albrecht (ORCID: https://orcid.org/0000-0002-4669-7670)
- Anna Skrzyńska (ORCID: https://orcid.org/0000-0002-2965-4097)
- Lesław Sieroń (ORCID: https://orcid.org/0000-0002-7797-0262)
- Artur Przydacz (ORCID: https://orcid.org/0000-0002-3479-8781)
Institutions
- Lodz University of Technology (PL)
- Institute of Organic Chemistry (PL)
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
Funders
- Narodowe Centrum Nauki