52280-74-7Relevant academic research and scientific papers
Synthesis of Methoxy-2-hydroxy-1,4-naphthoquinones and Reaction of One Isomer with Aldehydes under Basic Conditions
Ameer, Farouk,Giles, Robin G. F.,Green, Ivan R.,Pearce, Rene
, p. 1247 - 1258 (2007/10/03)
Two protocols for the synthesis of methoxy-2-hydroxy-1,4-naphthoquinones were investigated in order to evaluate their behavior towards aldehydes under amine-basic conditions. Both the nature of the quinone and aliphatic aldehyde contribute to the viability of this condensation as well as further transformations.
Regioselectivity in the Reactions of Methoxydehydrobenzenes with Furans. Part 2. 2-Methoxyfuran and Methoxydehydrobenzenes
Giles, Robin G. F.,Hughes, Andrew B.,Sargent, Melvyn V.
, p. 1581 - 1587 (2007/10/02)
Acid-induced ring opening of adducts of furan and methoxydehydrobenzenes gives the naphthalenols derived from the more stable carbocation.The cycloadditions of methoxydehydrobenzenes containing a 3-methoxy group and 2-methoxyfuran are highly regiospecific
Regiospecific Synthesis of Quinizarin and Naphthazarin Derivatives by Cycloaddition
Cameron, Donald W.,Feutrill, Geoffrey I.,McKay, Peter G.
, p. 2095 - 2109 (2007/10/02)
The diene (E)-1,1,4-trimethoxybuta-1,3-diene underwent regiospecific cycloaddition to derivatives of 2(3)-chloro-1,4-naphthoquinone.The resulting adducts were aromatized to give 1,4-dioxygenated anthraquinones.The latter were obtained as derivatives of quinizarin dimethyl ether or of quinizarin monomethyl ether depending on the conditions of aromatization.Cycloaddition of the diene to non-halogenated naphthoquinones proceeded similarly, orientation being controlled by substituents in the benzenoid ring.Analogous reaction of the diene with benzoquinones gave 5,8-dioxygenated naphthoquinones (naphthazarins), generally in limited yield.The procedure has been applied to synthesis of the mould metabolites helminthosporin and cynodontin
