AcBr/DMSO Mediated Sulfenylation of Pyrrolo[2,1-a]isoquinolines

被引：8
作者：
Chen, Xiao-Hui [1 ]
Cui, Hai-Lei [1 ]
机构：
[1] Chongqing Univ Arts & Sci, Coll Chem & Environm Engn, Lab Asymmetr Synth, Chongqing 402160, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 11期
基金：
中国国家自然科学基金;
关键词：
METAL-FREE SYNTHESIS; DIMETHYL-SULFOXIDE; REGIOSELECTIVE SULFENYLATION; TUBULIN POLYMERIZATION; POTENT INHIBITORS; BOND FORMATION; C-S; BROMINATION; DMSO; ALKALOIDS;
D O I：
10.1021/acs.joc.3c00566
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We have developed a mild sulfenylation of pyrrolo-[2,1-a]-isoquinolines with acetyl bromide and dimethyl sulfoxide.A widerange of functionalized pyrrolo-[2,1-a]-isoquinolinescould be prepared efficiently through the formation of a C-Sbond with thiophenols (27 examples, 36-94% yields). The currentstrategy can also be utilized for functionalization of pyrrolo-[1,2-a]-quinolines and indole.
引用
收藏
页码：7347 / 7361
页数：15
相关论文
共 60 条
[1]   Metal-free synthesis of 3-methylthiofurans from homopropargylic alcohols and DMSO via a tandem sulfenylation/cyclization reaction in a one-pot manner [J].
An, Zhenyu ;
She, Yue ;
Yang, Xiaodong ;
Pang, Xiaobo ;
Yan, Rulong .
ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (12) :1746-1749
[2]   METABOLITIES OF THE MARINE PROSOBRANCH MOLLUSK LAMELLARIA SP [J].
ANDERSEN, RJ ;
FAULKNER, DJ ;
HE, CH ;
VANDUYNE, GD ;
CLARDY, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (19) :5492-5495
[3]   Halogen and Chalcogen Cation Pools Stabilized by DMSO. Versatile Reagents for Alkene Difunctionalization [J].
Ashikari, Yosuke ;
Shimizu, Akihiro ;
Nokami, Toshiki ;
Yoshida, Jun-ichi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (43) :16070-16073
[4]   Microwave-Assisted Ullmann C-S Bond Formation: Synthesis of the P38α MAPK Clinical Candidate VX-745 [J].
Bagley, Mark C. ;
Davis, Terence ;
Dix, Matthew C. ;
Fusillo, Vincenzo ;
Pigeaux, Morgane ;
Rokicki, Michal J. ;
Kipling, David .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (21) :8336-8342
[5]   Anticancer Properties of Lamellarins [J].
Bailly, Christian .
MARINE DRUGS, 2015, 13 (03) :1105-1123
[6]  
Banwell MG, 2020, TARG HETEROCYCL SYST, V24, P208, DOI 10.17374/targets.2021.24.208
[7]   Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions [J].
Beletskaya, Irina P. ;
Ananikov, Valentine P. .
CHEMICAL REVIEWS, 2011, 111 (03) :1596-1636
[8]   Iron-Catalyzed Synthesis of Pyrrolo[2,1-a]isoquinolines via 1,3-Dipolar Cycloaddition/Elimination/Aromatization Cascade and Modifications [J].
Chen, Xiao-Hui ;
Pan, Yu-Yi ;
Wang, Wei-Xun ;
Cui, Hai-Lei .
SYNLETT, 2022, 33 (16) :1645-1654
[9]   Cu(II)-Mediated Methylthiolation of Aryl C-H Bonds with DMSO [J].
Chu, Lingling ;
Yue, Xuyi ;
Qing, Feng-Ling .
ORGANIC LETTERS, 2010, 12 (07) :1644-1647
[10]  
Cui H.-L., 2022, TARGETS HETEROCYCLIC, V26, P222
123456