Institute of Marine Biomedicine, Shenzhen Polytechnic, Shenzhen 518055, China.
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.
J Org Chem. 2020 May 15;85(10):6794-6802. doi: 10.1021/acs.joc.0c00374. Epub 2020 May 7.
Pyridinium 1,4-zwitterionic thiolates, as a novel kind of sulfur-containing synthon, have been applied to the synthesis of 12a-benzo[]pyrido[1,2-][1,4]thiazepines and benzo[]thiophenes. Benzopyridothiazepines were produced through a 1,5-dipolar cycloaddition reaction from pyridinium 1,4-zwitterionic thiolates with arynes, whereas benzothiophenes as side products were generated via a [3 + 2] cascade cyclization reaction. The [5 + 2] reaction mode of pyridinium 1,4-zwitterionic thiolates is disclosed for the first time.
吡啶鎓 1,4-内盐硫醇盐作为一种新型含硫砌块，已被应用于 12a-苯并[]吡啶[1,2-][1,4]噻嗪和苯并[]噻吩的合成。苯并吡啶噻嗪是通过吡啶鎓 1,4-内盐硫醇盐与芳炔的 1,5-偶极环加成反应生成的，而苯并噻吩则是通过[3+2]级联环化反应生成的副产物。吡啶鎓 1,4-内盐硫醇盐的[5+2]反应模式为首次报道。
