Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China.
Org Biomol Chem. 2022 Sep 28;20(37):7467-7471. doi: 10.1039/d2ob01391f.
Fused polycyclic pyrazoles are an important class of heterocyclic compounds; thus, the development of efficient methods for their preparation becomes highly urgent. Herein, we reported an efficient method for the synthesis of trifluoromethylated fused tricyclic pyrazoles intramolecular cyclization of cyclic ketone-derived amines. Mechanistic studies provide evidence for the generation of trifluoromethylated β-diazo ketones as intermediates diazotization with the use of -butyl nitrite. The synthetic utility of this method is highlighted by scale-up synthesis and the derivatization of the obtained fused tricyclic pyrazole products.
稠合多环吡唑是一类重要的杂环化合物；因此，开发其高效制备方法变得非常紧迫。在此，我们报道了一种通过环状酮衍生的胺的分子内环化反应来合成三氟甲基稠合三环吡唑的有效方法。机理研究为三氟甲基化β-重氮酮作为中间体的生成提供了证据，该中间体是通过使用正丁基亚硝酸酯进行重氮化反应得到的。该方法的合成实用性通过放大合成和获得的稠合三环吡唑产物的衍生化得到了突出体现。
