Umstead Weston J, Mukhina Olga A, Kutateladze Andrei G
Department of Chemistry and Biochemistry, University of Denver, Denver, 80208, USA.
European J Org Chem. 2015 Apr 1;2015(10):2205-2213. doi: 10.1002/ejoc.201403620.
Intramolecular cycloadditions of photogenerated azaxylylenes provide access to unprecedented polyheterocyclic scaffolds, suitable for subsequent postphotochemical modifications to further grow molecular complexity. Here we explore approaches to rapid "assembly" of novel photoprecursors with nitrogen/oxygen-rich tethers capable of producing potential pharmacophores and also compatible with subsequent 1,3-dipolar cycloadditions to furnish pentacyclic heterocycles with new structural cores, minimal number of rotatable bonds, and a high content of sp hybridized carbons. The modular "assembly" of the photoprecursors and potential variety of postphotochemical modifications of primary photoproducts provide framework for combinatorial implementation of this synthetic strategy.
光生氮杂亚苯的分子内环加成反应可用于构建前所未有的多杂环骨架，这些骨架适用于后续的光化学后修饰，以进一步增加分子复杂性。在此，我们探索了快速“组装”新型光前驱体的方法，这些前驱体带有富含氮/氧的连接基，能够产生潜在的药效基团，并且还与后续的1,3-偶极环加成反应兼容，以提供具有新结构核心、最少可旋转键数量和高sp杂化碳含量的五环杂环。光前驱体的模块化“组装”以及初级光产物潜在的多种光化学后修饰为这种合成策略的组合实施提供了框架。
