Oxidation with DMF/HIO4: A Convenient Preparation of Juglone |
| |
| Authors: | Antonio V Pinto Vitor F Ferreira Maria Do Carmo F R Pinto |
| |
| Institution: | 1. Núcleo de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro , Centro de Janeiro, Centro de Ciěncias da Saúde, Bloco H, 21941, Rio de Janeiro, RJ, Brazil;2. Núcleo de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro , Centro de Janeiro, Centro de Ciěncias da Saúde, Bloco H, 21941, Rio de Janeiro, RJ, Brazil;3. Instituto Nacional de Tecnologia-MIC , R. J., Brazil |
| |
| Abstract: | As part of an ongoing program directed toward the preparation of antraciclinones1 and aryl substituted lapachones2, which are important anticancer and antibiotic3 agents, we became interested in a efficient synthesis of substituted 1,4-naphthoquinones, such as juglone (3). This compound has received some attention due its activity as an allelophatic compound4. An extensive analysis of the literature procedures indicated that several methods are available starting from 1,5-dihydroxynaphthalene (1). All the procedures explored the oxidation of carbon four of the naphthyl ring by several known reagents, such as, chromium trioxide-piridine5, thallium trinitrate5, chromic acid6, peracetic acid7, dichromate8, iron (III) chloride9 and mercuric oxide10. None of the several known methods for the preparation of (3) proceeded in satisfactory yield (except for the thallium trinitrate method which gave 642 yield) and most of them gave a mixture of 1,2 and 1,4-naphthoquinone. |
| |
| Keywords: | |
|
|
