Synthesis 2019; 51(07): 1669-1679
DOI: 10.1055/s-0037-1610676
paper
© Georg Thieme Verlag Stuttgart · New York

Lewis Acid Catalyzed Regio- and Diastereoselective Synthesis of Spiroisoxazolines via One-Pot Sequential Knoevenagel Condensation/1,3-Dipolar Cycloaddition Reaction

Hossein Yazdani
,
Ayoob Bazgir*
Department of Chemistry, Shahid Beheshti University G.C., Tehran 1983963113, Iran   Email: a_bazgir@sbu.ac.ir
› Author Affiliations
We gratefully acknowledge the financial support from the Research Council of Shahid Beheshti University and the Iran National Science Foundation (INSF) (Project Number 96011205).
Further Information

Publication History

Received: 31 October 2018

Accepted after revision: 08 November 2018

Publication Date:
09 January 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.

Supporting Information

 
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