TY - JOUR A1 - Asahara, Haruyasu A1 - Hiraishi, Minami A1 - Nishiwaki, Nagatoshi T1 - One-pot and metal-free synthesis of 3-arylated-4-nitrophenols via polyfunctionalized cyclohexanones from β-nitrostyrenes JF - Beilstein Journal of Organic Chemistry PY - 2020/// VL - 16 SP - 1830 EP - 1836 SN - 1860-5397 DO - 10.3762/bjoc.16.150 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.16.150 KW - 3-arylated-4-nitrophenol KW - Danishefsky’s diene KW - Diels–Alder reaction KW - nitroalkene KW - polysubstituted cyclohexanone N2 - β-Nitrostyrenes underwent a 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, e.g., a thienyl group could be introduced into the nitrophenol framework. ER -