A novel and efficient method to prepare 2-aryltetrahydrofuran-2-ylphosphonic acids

• Vsevolod V. Komissarov,
• Anatoly M. Kritzyn and
• Jouko J. Vepsäläinen

Beilstein J. Org. Chem. 2010, 6, No. 63, doi:10.3762/bjoc.6.63

• 10.3762/bjoc.6.63 Abstract A novel one-pot method was developed for the synthesis of the title compounds starting from 4-chloro-1-aryl-1-butanones 1, phosphorus trichloride and acetic acid. The end products 2 were obtained in 20–94% yield. The cyclization step under acidic conditions probably occurs as a

• result of anchimeric assistance of the phosphonic acid group. Keywords: 4-chloro-1-aryl-1-butanones; cyclization; furan; heterocycle; phosphonic acids; Introduction Our laboratory has conducted systematic evaluation of polymethylene derivatives of nucleic bases with various terminal functional groups

• phosphorylase and thymidine phosphorylase, enzymes which have been targeted in a number of serious diseases [5][6][7]. Recently, we prepared nucleic base derivatives with a terminal Ph-CO-group by alkylation methods starting from 4-chloro-1-aryl-1-butanones 1 [8]. According to the studies of Conant et al. [9