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Dieckmann缩合
JOURNAL OF ORGANIC CHEMISTRY · 2023 · IF 3.6

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

Yuan Li,Jiamei Shen,Yawei Shen,Yanfeng Li,Kai Luo,Lei Wu

A novel and efficient tandem SN2 nucleophilic substitution/Dieckmann condensation reaction of α-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.

CAS / MDL: 1310-73-2
研究领域: 有机化学 · 药物化学
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