UNEXPECTED FORMATION OF BENZOFURAN DERIVATIVES IN THE C-AMIDOALKYLATION OF p-CRESOL WITH 4-CHLORO-N-(2,2-DICHLORO-2-PHENYLETHYLIDENE)BENZENESULFONAMIDE

作者：Serykh V Yu; Rozentsveig I B^*; Rozentsveig G N; Chernyshev K A

来源：Chemistry of Heterocyclic Compounds, 2012, 47(11): 1339-1344.

• benzofurans
• p-cresol
• imines
• sulfonamides
• C-amidoalkylation
• acid catalysis
• heterocyclization
• nucleophilic addition

The C-amidoalkylation of p-cresol with 4-chloro-N-(2,2-dichloro-2-phenylethylidene)benzenesulfonamide in the presence of H2SO4, oleum, or a mixture of H2SO4 and P4O10 was studied for the first time. It was shown that the reaction not only leads to the targeted 4-chloro-N-[2,2-dichloro-1-(2-hydroxy-5-methylphenyl)-2-phenylethyl]benzenesulfonamide but is also accompanied by unexpected formation of the heterocyclic derivatives 4-chloro-N-(5-methyl-2-phenyl-1-benzofuran-3-yl)benzenesulfonamide and 5-methyl-3-phenyl-2-benzofuran-2(3H)-one.

• 出版日期2012-2