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.
Sn-PILC: A novel efficient and recyclable catalyst for one-pot three component Povarov’s inverse-electron-demand hetero Diels-Alder reaction for a facile synthesis of tetrahydropyranoquinoline derivatives under neat conditions.