63374-34-5Relevant articles and documents
Free-radical cyclization approach to polyheterocycles containing pyrrole and pyridine rings
Khlebnikov, Alexander F.,Mosiagin, Ivan P.,Novikov, Mikhail S.,Spiridonova, Darya V.,Tomashenko, Olesya A.,Tunik, Sergey P.
supporting information, p. 1490 - 1498 (2021/07/02)
A wide range of derivatives with new pyrido[2,1-a]pyrrolo[3,4-c]isoquinoline skeleton was synthesized by free-radical intramolecular cyclization of o-bromophenyl-substituted pyrrolylpyridinium salts using the (TMS)3SiH/AIBN system. The cyclizat
Diversified Transformations of Tetrahydroindolizines to Construct Chiral 3-Arylindolizines and Dicarbofunctionalized 1,5-Diketones
Feng, Xiaoming,He, Qianwen,Liu, Xiaohua,Pan, Chenjing,Su, Zhishan,Wu, Zhikun,Zhang, Dong,Zhou, Yuqiao
supporting information, p. 15975 - 15985 (2020/10/18)
Enantioselective diverse synthesis of a small-molecule collection with structural and functional similarities or differences in an efficient manner is an appealing but formidable challenge. Asymmetric preparation and branching transformations of tetrahydroindolizines in succession present a useful approach to the construction of N-heterocycle-containing scaffolds with functional group, and stereochemical diversity. Herein, we report a breakthrough toward this end via an initial diastereo- A nd enantioselective [3 + 2] cycloaddition between pyridinium ylides and enones, following diversified sequential transformations. Chiral N,N′-dioxide-earth metal complexes enable the generation of optically active tetrahydroindolizines in situ, across the strong background reaction for racemate-formation. In connection with deliberate sequential transformations, involving convenient rearomatic oxidation, and light-active aza-Norrish II rearrangement, the tetrahydroindolizine intermediates were converted into the final library including 3-arylindolizine derivatives and dicarbofunctionalized 1,5-dicarbonyl compounds. More importantly, the stereochemistry of four-stereogenic centered tetrahydroindolizine intermediates could be efficiently transferred into axial chirality in 3-arylindolizines and vicinal pyridyl and aryl substituted 1,5-diketones. In addition, densely functionalized cyclopropanes and bridged cyclic compounds were also discovered depending on the nature of the pyridinium ylides. Mechanism studies were involved to explain the stereochemistry during the reaction processes.
Transition-Metal-Free Synthesis of Indolizines from Electron-Deficient Alkenes via One-Pot Reaction Using TEMPO as an Oxidant
Shi, Fei,Zhang, Yu,Lu, Zhaole,Zhu, Xiaolei,Kan, Weiqiu,Wang, Xiang,Hu, Huayou
, p. 413 - 420 (2016/01/28)
A one-pot method for the synthesis of multisubstituted indolizines from α-halo carbonyl compounds, pyridines, and electron-deficient alkenes is reported. The oxidative dehydrogenation reaction takes place under transition-metal-free conditions using TEMPO as an oxidant. This protocol uses ready available starting materials in a convenient procedure under mild reaction conditions.