Institute of Marine Biomedicine/Hoffmann Institute of Advanced Materials, Shenzhen Polytechnic, Shenzhen 518055, China.
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.
Org Lett. 2020 Aug 7;22(15):5817-5821. doi: 10.1021/acs.orglett.0c01888. Epub 2020 Jul 10.
Two reaction modes of pyridinium 1,4-zwitterionic thiolates with sulfenes generated in situ from alkanesulfonyl chlorides are described with DIPEA as the base. 3-1,2-Dithiole 2,2-dioxides could be obtained via a formal [3 + 2] pathway from alkylmethanesulfonyl chlorides, while 1,9a-dihydropyrido[2,1-][1,4]thiazines were obtained via a stepwise [(5 + 2) - 1] pathway from phenylmethanesulfonyl chlorides. Moreover, as an application, indolizines could be accessed via a stepwise {[(5 + 2) - 1] - 1} pathway, with 1,9a-dihydropyrido[2,1-][1,4]thiazines as the transient intermediates.
两种吡啶 1,4-双 zwitterionic 硫醇盐与烷基亚磺酰氯原位生成的亚磺烯的反应模式被描述，其中 DIPEA 作为碱。3-1,2-二硫杂环戊烷 2,2-二氧化物可以通过烷基亚磺酰氯的正式 [3 + 2] 途径获得，而 1,9a-二氢吡啶并[2,1-][1,4]噻嗪则可以通过苯基亚磺酰氯的分步 [(5 + 2) - 1] 途径获得。此外，作为一种应用，吲唑可以通过分步 {[(5 + 2) - 1] - 1} 途径获得，其中 1,9a-二氢吡啶并[2,1-][1,4]噻嗪作为瞬态中间体。
