Synthesis of N-benzylated indole-, indazole- and benzotriazole-4,7-diones |
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Authors: | Christelle Marminon |
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Institution: | Laboratoire de Chimie Organique, Université de Lyon, Lyon, F-69003, France; université Lyon 1, ISPB, EA 3741 ‘Ecosystèmes et Molécules Bioactives’, 8 avenue Rockefeller, Lyon Cedex 08, F-69373, France |
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Abstract: | The benzylation of 4,7-dimethoxy-1H-indole (5) followed by an oxidative demethylation led to 1-benzyl-1H-indole-4,7-dione (2) with a 73% overall yield. From the commercially available 7-nitro-1H-indazole (7), a three-step pathway was developed to access 1-benzyl-1H-indazole-4,7-dione (3). Two of these steps were investigated in order to improve the process. The direct synthesis of 1-benzyl-1H-benzotriazole-4,7-dione (4), through a 1,3-dipolar cycloaddition between benzyl azide and para-benzoquinone (13), was also studied. The simplicity of the methodologies described offers wide perspectives in obtaining 1-alkylated indole-, indazole- and benzotriazole-4,7-diones. |
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Keywords: | N-Benzylation Oxidative demethylation Catalytic hydrogenation 1 3-Dipolar cycloaddition |
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