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Synthesis 2019; 51(07): 1669-1679
DOI: 10.1055/s-0037-1610676
DOI: 10.1055/s-0037-1610676
paper
Lewis Acid Catalyzed Regio- and Diastereoselective Synthesis of Spiroisoxazolines via One-Pot Sequential Knoevenagel Condensation/1,3-Dipolar Cycloaddition Reaction
We gratefully acknowledge the financial support from the Research Council of Shahid Beheshti University and the Iran National Science Foundation (INSF) (Project Number 96011205).Weitere Informationen
Publikationsverlauf
Received: 31. Oktober 2018
Accepted after revision: 08. November 2018
Publikationsdatum:
09. Januar 2019 (online)
Abstract
A ZnCl2-catalyzed regio- and diastereoselective one-pot sequential Knoevenagel condensation/1,3-dipolar cycloaddition reaction of CH acids (oxindole, 1,3-indandione, and 3H-pyrazol-3-one), aldehydes, and dibromoformaldoxime has been established. The method allows the synthesis of diversely functionalized spiroisoxazolines in good isolated yields under mild reaction conditions. Moreover, the preparation of spiroindene-isoxazole-1,3-diones containing benzoimidazole or benzothiazole moieties as new ligands for the metal-catalyzed coupling reactions and C–H activation is demonstrated.
Keywords
1,3-dipolar cycloaddition reaction - isoxazolines - nitrile oxides - spirooxindoles - spiroindandiones - coupling reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610676.
- Supporting Information
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