Novel Synthesis of 3-Aryl-4-hydroxybenzofurans via Four-Component Reaction from Substituted Nitrostyrenes, Aromatic Aldehydes, Cyclohexan-1,3-diones, and Ammonium Acetate

作者：Li, Yan; Liu, Hui; Sun, Liang; Liu, Juanjuan; Xue, Zhiheng; Yao, Juan; Wang, Cunde^*

来源：Synlett, 2013, 24(14): 1851-1855.

DOI：10.1055/s-0033-1339332

• multicomponent reaction
• 4-hydroxybenzofuran
• substituted beta-nitrostyrene
• dehydroaromatization
• cyclohexane-1,3-dione

An one-pot-reaction methodology was developed to synthesize a variety of polysubstituted 3-aryl-2-arylmethylene amino-4-hydroxybenzofurans from substituted beta-nitrostyrenes, aromatic aldehydes, ammonium acetate, and cyclohexane-1,3-diones for the generation of a wide range of structurally interesting and pharmacologically significant compounds. The reaction pathway involves Michael addition of substituted nitrostyrenes and cyclohexane-1,3-diones, then nucleophilic addition of 2-(2-nitro-1-phenylethyl) cyclohexane-1,3-dione and Schiff base generated from aromatic aldehyde and ammonium acetate and intramolecular cyclization, followed by dehydroaromatization to afford the corresponding 3-aryl-2-arylmethyleneamino-4-hydroxybenzofurans.

• 出版日期2013-9
• 单位扬州大学