Synthesis of 3′,4′‐Diaryl‐4′H‐spiro[indoline‐3,5′‐[1′,2′,4′]oxadiazol]‐2‐ones via DMAP‐catalyzed Domino Reactions and Their Antibacterial Activity |
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| Authors: | Guanghao Shi Xinwei He Yongjia Shang Liwei Xiang Cheng Yang Guang Han Bing Du |
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| Institution: | 1. Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule‐Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China;2. Institute of Biomedical Sciences, School of Life Sciences, East China Normal University, Shanghai 200241, China |
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| Abstract: | A convenient and metal‐free DMAP‐catalyzed domino reaction of isatins, arylamines and hydroximoyl chlorides has been developed to achieve 1,3‐dipolar cycloaddition of imines into aryl nitrile oxides at ambient temperature. In this one‐pot transformation, a 1,2,4‐oxadiazole skeleton was efficiently formed. This methodology needs no extra additives and features wide substrate scope, good functional group tolerance and mild reaction conditions. A plausible mechanism for this process was proposed. Moreover, the antibacterial activities of the products were evaluated towards Staphylococcus epidermidis, Staphylococcus aureus, Escherichia coli and Klebsiella pneumoniae using the Broth microdilution method. |
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| Keywords: | 4‐dimethylaminopyridine antimicrobial activity isatins domino reactions oxadiazoles |
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