Tandem SN2 Nucleophilic Substitution/Phospho-Dieckmann Reaction: One-Step Synthesis of 2-Phosphonyl-3-hydroxybenzo[b]thiophenes

A novel and efficient tandem S(N)2 nucleophilic substitution/Dieckmann condensation reaction of a-iodomethyl phosphine oxide with methyl thiosalicylate derivatives has been developed by using NaOH as a base, which enables the expeditious synthesis of 2-phosphonyl-3-hydroxybenzo[b]thiophene derivatives in moderate to high yields under simple conditions. This research provides not only a convenient method for the functionalization of benzo[b]thiophenes at the 2-position and 3-position but also new organophosphorus molecules. Furthermore, several new phosphonyl-substituted benzo[b]thiophenes were obtained from the resultant 2-phosphonyl-3-hydroxybenzo[b]thiophenes.

Automated summary

A novel and efficient reaction method using NaOH as a base has been developed for the tandem S(N)2 nucleophilic substitution/Dieckmann condensation reaction of a-iodomethyl phosphine oxide with methyl thiosalicylate derivatives. This method enables the rapid synthesis of 2-phosphonyl-3-hydroxybenzo[b]thiophene derivatives under simple conditions. Furthermore, several new phosphonyl-substituted benzo[b]thiophenes were obtained from the resultant 2-phosphonyl-3-hydroxybenzo[b]thiophenes.