Key Laboratory for Large-Format Battery Materials and System Ministry of Education, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan, 430074, P. R. China.
Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, 832004, P. R. China.
ChemSusChem. 2022 Oct 21;15(20):e202201301. doi: 10.1002/cssc.202201301. Epub 2022 Sep 13.
A highly efficient and elegant diversity-oriented reaction paradigm employing atropaldehyde acetals as new dual C2/C3 synthons was developed under metal-free conditions using glycine esters as the counterpart reagents, which allowed rapid synthesis of two important nitrogen-containing heterocycles, pyrrolo[1,2-a]quinolines and 3,5-diarylpyridines. The divergent products are subtly controlled by the manipulation of the substitutional groups of glycine esters. When a N-arylglycine ester was used, pyrrolo[1,2-a]quinolines can be formed through cascade oxidative C-C cleavage/multiple cyclization. Instead, N-benzylglycine ester as the counter-reagent led to the synthesis of 3,5-diarylpyridines via two key C-N cleavages. Mild conditions, broad substrate scope, scalability and environmentally acceptable organic solvents rendered this method practical and attractive.
发展了一种高效、优雅的多样性导向反应模式，在无金属条件下，采用芳基乙醛缩醛作为新型双 C2/C3 合成子，甘氨酸酯作为对应试剂，快速合成了两个重要的含氮杂环，吡咯并[1,2-a]喹啉和 3,5-二芳基吡啶。通过对甘氨酸酯取代基的操作，可以微妙地控制不同的产物。当使用 N-芳基甘氨酸酯时，可以通过级联氧化 C-C 断裂/多次环化形成吡咯并[1,2-a]喹啉。相反，使用 N-苄基甘氨酸酯作为反试剂，则通过两个关键的 C-N 断裂导致 3,5-二芳基吡啶的合成。温和的条件、广泛的底物范围、可扩展性和环境可接受的有机溶剂使该方法具有实用性和吸引力。
