Green Catalysis Center and College of Chemistry, Zhengzhou University, Zhengzhou 450001, China.
Org Lett. 2022 May 6;24(17):3286-3290. doi: 10.1021/acs.orglett.2c01183. Epub 2022 Apr 21.
A transition-metal-free C═C double bond cleavage reaction employing molecular iodine is described. In the presence of KCO as the base, I-mediated C═C bond cleavage followed by intramolecular annulation of -(2-vinylaryl)pyridin-2-amine substrates produces pyrido[2,1-]quinazolinones and related heterocyclic compounds. This reaction can be completed on a gram scale and has been successfully applied to the synthesis of compounds with important biological properties, including efflux pump inhibitory and antiallergic activities.
本文描述了一种无需过渡金属的 C═C 双键断裂反应，该反应采用了分子碘。在 KCO 作为碱的存在下，I 介导的 C═C 键断裂，随后 -(2-乙烯基芳基)吡啶-2-胺底物进行分子内环化，生成吡啶并[2,1-]喹唑啉酮和相关杂环化合物。该反应可以在克级规模下完成，并已成功应用于具有重要生物性质的化合物的合成，包括外排泵抑制剂和抗过敏活性。
