138779-63-2Relevant academic research and scientific papers
Studies on the oxidative cyclization of 3-hydroxyalkyl-1,2,4- trialkoxynaphthalenes and synthetic application for the biologically active natural compound rhinacanthone
Ogata, Tokutaro,Doe, Misae,Matsubara, Aya,Torii, Eri,Nishiura, Chiaki,Nishiuchi, Arisa,Kobayashi, Yusuke,Kimachi, Tetsutaro
, p. 502 - 509 (2014)
The oxidative intramolecular cyclization of 3-hydroxyalkyl-1,2,4- trimethoxynaphthalenes was investigated. A series of 1,2-naphthoquinone fused cyclic ethers were synthesized directly from 3-hydroxyalkyl-1,2,4- trimethoxynaphthalenes by exposure to diammonium cerium (IV) nitrate. To understand the reaction mechanism, the intramolecular cyclization of 3-hydroxyalkyl-naphthoquinones that were formed as reaction intermediates was also examined. The results suggested that the reaction proceeds by a stepwise oxidation-cyclization mechanism. Using this methodology, five-step synthesis of rhinacanthone was achieved with high yield.
