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Paper | Regular issue | Vol 55, No. 2, 2001, pp.265-277
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9079
Regioselective Friedel-Crafts Acylation with Unsymmetrically Substituted Furan-dicarboxylic Acid Anhydride and Furan Acid Chloride: Syntheses of 4-Substituted 3-Arylcarbonyl-2-phenylfuran and 3-Substituted 4-Arylcarbonyl-2-phenylfuran

Shrong-Shi Lin, Xiao-Ping Nie, Jun-Hua Yu, and Xiu-Lin Ye*

*Department of Chemistry, Peking University, Beijing 100871, China

Abstract

Friedel-Crafts acylation of aromatic compounds with 2-phenylfuran-3,4-dicarboxylic acid anhydride (4) and 3-methoxycarbonyl-2-phenylfuran-4-carboxylic acid chloride (6) was studied. The reaction with 4, unsymmetrically substituted cyclic anhydrides, afforded 2-phenyl-3-arylcarbonylfuran-4-carboxylic acids (7) in moderate to good yields. Possible mechanism for such regioselective ring opening was also proposed. No interchanged isomeric product was noted for acylation of aromatic compounds with ester acid chloride (6). The synthesis of the precursor of 6, 3-methoxycarbonyl-2-phenylfuran-4-carboxylic acid (5), was achieved by regioselective hydrolysis from dimethyl 2-phenylfuran-3,4-dicarboxylate (2).