Satyam Killari, Harish Battu, Nanubolu Jagadeesh Babu, Suresh Surisetti
Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500 007, India.
Laboratory of X-Ray Crystallography, Department of Analytical Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500 007, India.
Chem Commun (Camb). 2020 Mar 3;56(18):2803-2806. doi: 10.1039/d0cc00321b.
Herein we describe an NHC-catalyzed umpolung of β-carboline-based cyclic imines for their conversion to the corresponding N-substituted cyclic amides. The key to the success of this transformation appears to be that NHC upon reaction with the imine concomitantly goes through the generation of an aza-Breslow intermediate and aza-Michael addition followed by oxidation with molecular oxygen to deliver the N-substituted amide products. The developed method has enabled the synthesis of various biologically relevant β-carboline-1-one derivatives in good yields.
在此，我们描述了一种N-杂环卡宾催化的基于β-咔啉的环状亚胺的极性翻转，用于将其转化为相应的N-取代环状酰胺。这种转化成功的关键似乎是N-杂环卡宾与亚胺反应时，会同时生成氮杂-Breslow中间体并进行氮杂-Michael加成，随后用分子氧氧化以得到N-取代酰胺产物。所开发的方法能够以良好的产率合成各种具有生物学相关性的β-咔啉-1-酮衍生物。
