Liu Shiqi, Zhang Kun, Meng Yutong, Xu Jiaxi, Chen Ning
Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, P. R. China.
Org Biomol Chem. 2023 Aug 30;21(34):6892-6897. doi: 10.1039/d3ob01147j.
Tetrahydroisoquinoline and its fused polyheterocycles are prevalent structural motifs found in numerous natural products. In this study, we report a highly efficient and convergent synthetic approach for the construction of tetrahydroisoquinoline-fused polyheterocycles through a three-component formal [2 + 2 + 2] annulation process by combining 3,4-dihydroisoquinolines, CO, and benzynes. Notably, electron-rich 3,4-dihydroisoquinolines and electron-deficient benzynes exhibit greater reactivity in this annulation. Moreover, this method benefits from the convergent synthesis and the utilization of carbon dioxide, providing a valuable strategy for the facile synthesis of tetrahydroisoquinoline-fused polyheterocycles, with potential applications in the discovery and development of novel organic molecules.
四氢异喹啉及其稠合多杂环是众多天然产物中普遍存在的结构基序。在本研究中，我们报道了一种高效且收敛的合成方法，通过将3,4 - 二氢异喹啉、CO和苯炔进行三组分形式的[2 + 2 + 2]环化反应来构建四氢异喹啉稠合多杂环。值得注意的是，富电子的3,4 - 二氢异喹啉和缺电子的苯炔在该环化反应中表现出更高的反应活性。此外，该方法受益于收敛合成以及二氧化碳的利用，为四氢异喹啉稠合多杂环的简便合成提供了一种有价值的策略，在新型有机分子的发现和开发中具有潜在应用。
