β-Nitrostyrenes underwent the Diels-Alder reaction with Danishefsky’s diene to afford cyclohexenes together with the corresponding hydrolyzed products, 3-arylated 5-methoxy-4-nitrocyclohexanones. When the reaction was conducted in the presence of water, the cyclohexenes were efficiently hydrolyzed into cyclohexanones. Subsequent aromatization by heating the cyclohexanone with a catalytic amount of iodine in dimethyl sulfoxide gave 3-arylated 4-nitrophenols. The reaction of nitrostyrenes with Danishefsky’s diene could be conducted in one-pot to directly afford the corresponding nitrophenols. Moreover, a heteroaryl group such as a thienyl group could be introduced into the nitrophenol framework.
Keywords: Diels-Alder reaction; Danishefsky’s diene; Nitroalkene; 3-Arylated 4-nitrophenol; Polysubstituted cyclohexanone
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Asahara, H.; Hiraishi, M.; Nishiwaki, N. Beilstein Arch. 2020, 202063. doi:10.3762/bxiv.2020.63.v1
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