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

被引：38
作者：
Cheng, Bin [1 ,2 ]
Li, Yuntong [2 ]
Zhang, Xinping [1 ,2 ]
Duan, Shengguo [4 ]
Li, Hui [1 ,2 ]
He, Yixuan [1 ,2 ]
Li, Yun [2 ]
Wang, Taimin [1 ]
Zhai, Hongbin [1 ,2 ,3 ]
机构：
[1] Shenzhen Polytech, Inst Marine Biomed, Hoffmann Inst Adv Mat, Shenzhen 518055, Peoples R China
[2] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[3] Peking Univ, State Key Lab Chem Oncogen, Shenzhen Engn Lab Nano Drug Slow Release, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China
[4] Zhejiang Sci Tech Univ, Dept Chem, Hangzhou 310018, Peoples R China
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 15期
关键词：
NITROGEN-BRIDGED HETEROCYCLES; LEINAMYCIN; SULFUR; THIOSULFONATES; CYTOTOXICITY; STREPTOMYCES; DERIVATIVES; PRECURSORS; CHEMISTRY; 1-OXIDES;
D O I：
10.1021/acs.orglett.0c01888
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：5817 / 5821
页数：5
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