Synthesis of new 1H-1,2,3-triazole-1,4-naphthoquinones

<em>In this work, were synthesized new 1H-1,2,3-triazole-1,4-naphthoquinones via 1,3-dipolar cycloaddition reaction using CuI/acetonitrile without addition of base or ligand. The compounds (3a-i) were obtained in moderate-to-good yields 45-92%. To prepare (3d), we obtain a mixture of (3d) and...

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Bibliographic Details
Main Authors: Wagner O. Valença, Celso A. Camara, Ronaldo N. de Oliveira
Format: Article
Language:English
Published: Universidade Federal de Mato Grosso do Sul 2012-06-01
Series:Orbital: The Electronic Journal of Chemistry
Subjects:
Online Access:http://orbital.ufms.br/index.php/Chemistry/article/view/352
Description
Summary:<em>In this work, were synthesized new 1H-1,2,3-triazole-1,4-naphthoquinones via 1,3-dipolar cycloaddition reaction using CuI/acetonitrile without addition of base or ligand. The compounds (3a-i) were obtained in moderate-to-good yields 45-92%. To prepare (3d), we obtain a mixture of (3d) and (4) in a ratio 3:1, that it was difficult to separate. The low yield for the compound (3f) can be also justified based in the formation of aminonaphthoquinone (4). The acetylation of (3h) and (3i) afforded the compounds (5) and (6) in 77% and 35% of yields, respectively. The low yield of (6) was due to formation of 35 % of the elimination product (7).</em>
ISSN:1984-6428