Synthesis of indolizines from pyridinium 1,4-zwitterionic thiolates and α-functionalized bromoalkanes <i>via</i> a stepwise [(5+1)−1] pathway
Bin Cheng, Xinping Zhang, Yuntong Li, Hui Li, Yixuan He, Yun Li, Taimin Wang, Hongbin Zhai
Abstract
The synthesis of pyridothiazines was achieved using pyridinium 1,4-zwitterionic thiolates and α-functionalized bromoalkanes via a formal [5+1] pathway. Further studies demonstrated that the synthesis of indolizines could be accomplished via a stepwise [(5+1)-1] pathway with unstable pyridothiazines as the transient intermediates from the same starting materials. The net transformation involves a sequence of annulation, oxidation and ring-contraction/desulfuration.
Topics & Concepts
PyridiniumChemistryIndolizineMedicinal chemistryCombinatorial chemistrySynthesis and Reactivity of HeterocyclesCyclopropane Reaction MechanismsSynthesis and Characterization of Pyrroles