Green synthetic approaches to furoylnaphthohydroquinone and juglone

• BENITES JULIO ^[1] ; CORTES MICHAEL ^[1] ; MIRANDA LUIS ^[1] ; ESTELA CYNTHIA ^[1] ; RIOS DAVID ^[1] ; ARENAS JORGE ^[1] ; VALDERRAMA JAIME A. ^[1]
  1. [1] Universidad Arturo Prat

     Universidad Arturo Prat

     Iquique, Chile

     
• Localización: Journal of the Chilean Chemical Society (Boletín de la Sociedad Chilena de Química), ISSN-e 0717-6309, ISSN 0366-1644, Vol. 59, Nº. 2, 2014, págs. 2455-2457
• Idioma: inglés
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• Resumen

  • The synthesis of two valuable precursors of biological active compounds named 2-(furan-2-yl)-1,4-dihydroxynapthohydroquinone 2 and 5-hydroxy-1,4-naphthoquinone (4, juglone) via solar photo-induced reactions from 1,4-naphthoquinone 1 and 1,5-dihydroxynaphthalene 3 in green solvent media is reported. When t-butyl alcohol and the binary t-ButOH/DMK and ternary i-PrOAc/DMK/MEK solvent mixtures were used, acylhydroquinone 2 was isolated in yields of 80, 83 and 77%, respectively. The sensitized photooxygenation of 3 "on water" and in water containing sodium dodecyl sulfate produce juglone 4 in 81 and 39% yields respectively.