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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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