期刊
TETRAHEDRON
卷 63, 期 3, 页码 735-739出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2006.10.086
关键词
N-benzylation; oxidative demethylation; catalytic hydrogenation; 1,3-dipolar cycloaddition
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. (c) 2006 Elsevier Ltd. All rights reserved.
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