Two Reaction Modes of Pyridinium 1,4-Zwitterionic Thiolates with Sulfenes: Synthesis of 3H-1,2-Dithiole 2,2-Dioxides, 1,9a-Dihydropyrido[2,1-c][1,4]thiazines, and Indolizines
Two Reaction Modes of Pyridinium 1,4-Zwitterionic Thiolates with Sulfenes: Synthesis of 3H-1,2-Dithiole 2,2-Dioxides, 1,9a-Dihydropyrido[2,1-c][1,4]thiazines, and Indolizines
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吡啶鎓 1,4-两性离子硫醇盐与亚砜的两种反应模式：合成 3H-1,2-二硫醇 2,2-二氧化物、1,9a-二氢吡啶并[2,1-c][1,4]噻嗪和吲嗪
DOI：
10.1021/acs.orglett.0c01888
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发表时间：
2020-08-07
期刊：
影响因子：
5.2
通讯作者：
Zhai，Hongbin
中科院分区：
文献类型：
--
作者：
Cheng，Bin;Li，Yuntong;Zhai，Hongbin
以DIPEA为碱，研究了1，4-两性硫醇吡啶盐与烷基磺酰氯原位生成的次磺酰基的两种反应模式。以烷基甲磺酰氯为原料，经[3 + 2]途径得到3 H-1，2-二硫杂环戊烯2，2-二氧化物，以苯基甲磺酰氯为原料，经[（5 + 2）-1]途径得到1，9 a-二氢吡啶并[2，1-c][1，4]噻嗪。此外，作为应用，中氮茚可以通过逐步{[（5 + 2）-1]-1}途径获得，其中1，9a-二氢吡啶并[2，1-c][1，4]噻嗪作为瞬时中间体。
Two reaction modes of pyridinium 1,4-zwitterionic thiolates with sulfenes generated in situ from alkanesulfonyl chlorides are described with DIPEA as the base. 3H-1,2-Dithiole 2,2-dioxides could be obtained via a formal [3 + 2] pathway from alkylmethanesulfonyl chlorides, while 1,9a-dihydropyrido[2,1-c][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-c][1,4]thiazines as the transient intermediates.