School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, 221116, P. R. China.
School of Materials and Chemical Engineering, Xuzhou University of Technology, Xuzhou 221018, P. R. China.
Chem Commun (Camb). 2022 Mar 31;58(27):4376-4379. doi: 10.1039/d2cc00206j.
A novel metal-free nitrative bicyclization of 1,7-diynes with BuONO in the presence of HO is reported, producing three types of skeletally diverse tricyclic pyrroles, namely pyrrolo[3,4-]quinolines, chromeno[3,4-]pyrroles and benzo[]isoindoles, with moderate to good yields by simply tuning the linkers of the 1,7-diynes. This domino protocol demonstrates remarkable compatibility regarding 1,7-diynes with different linkers, such as nitrogen and oxygen atoms and a hydroxymethyl group, and BuONO plays dual roles as a nitro precursor as well as a nitrogen atom source.
报道了一种新型的无金属硝化物双环化反应，在 HO 的存在下，1,7-二炔与 BuONO 反应，生成了三种骨架不同的三环吡咯，即吡咯并[3,4-]喹啉、色烯并[3,4-]吡咯和苯并[]异吲哚，通过简单地调节 1,7-二炔的连接物，产率中等至良好。该串联反应对具有不同连接物的 1,7-二炔具有显著的兼容性，如氮和氧原子以及羟甲基，并且 BuONO 发挥了双重作用，既是硝基前体又是氮原子源。
