Synthesis of Multifunctionalized Thiazolidine-4-thiones via [2+2+1] Annulation of Isothiocyanates and CF3-Imidoyl Sulfoxonium Ylides

被引：6

作者：

Ding, Yuhao ^{[1
]}

Guo, Hailin ^{[1
]}

Fan, Jingwen ^{[1
]}

Li, Zhiyong ^{[1
]}

Cheng, Guolin ^{[1
]}

机构：

[1] Huaqiao Univ, Coll Mat Sci & Engn, Xiamen Key Lab Optoelect Mat & Adv Mfg, Xiamen 361021, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2023年 / 365卷 / 24期

关键词：

Sulfoxonium ylide; Isothiocyanate; Annulation; Trifluoromethyl group; Thiazolidine-4-thiones; FLUORINE; ACTIVATION; AGENTS;

D O I：

10.1002/adsc.202300896

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

2-Iminothiazolidin-4-one, 5-ethylidenethiazolidin-4-one, and thiazolidine-4-thione are all medicinally relevant structures. In this work, a NaSO2CF3-promoted [2+2+1] cascade annulation reaction of CF3-imidoyl sulfoxonium ylides and isothiocyanates was reported to synthesize a variety of decorated thiazolidine-4-thiones in 35-91% yields with exclusive stereoselectivity. The gram-scale reaction and further chemoselective S-alkylations demonstrated the synthetic utilities of this transformation.

引用

页码：4672 / 4676

页数：5

共 50 条

[21] Rh(III)-Catalyzed C-H Cyclization of 2-Arylbenzimidazoles with CF3-Imidoyl Sulfoxonium Ylides and Further Sc(III)-Catalyzed Deaminative Hydroxylation
Liao, Juting
Zhai, Ruirui
Gao, Xiaoyang
Wu, Hongliang
Kong, Dulin
Wang, Shuojin
Chen, Xun
ADVANCED SYNTHESIS & CATALYSIS, 2024,
[22] Synthesis of indolines via palladium-catalyzed [4+1] annulation of (2-aminophenyl)methanols with sulfoxonium ylides
Hao, Erxiao
Kong, Xiaomei
Xu, Tongyu
Zeng, Fanlong
ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (31) : 6342 - 6351
[23] Construction of trifluoromethyl-substituted enaminones via rhodium (III)-catalyzed aldehydic C(sp2)-H bond activation of N-sulfonyl-2-aminobenzaldehydes with CF3-imidoyl sulfoxonium ylides
Duan, Yubo
Quan, Zhaolin
Chen, Zhengkai
TETRAHEDRON, 2025, 171
[24] Rhodium(iii)-catalyzed regioselective C2-alkenylation of indoles with CF3-imidoyl sulfoxonium ylides to give multi-functionalized enamines using a migratable directing group
Yang, Zuguang
Tang, Jianhua
Li, Chen
Chen, Zhengkai
Wu, Xiao-Feng
CHEMICAL COMMUNICATIONS, 2023, 59 (03) : 318 - 321
[25] Synthesis of 4-(Trifluoromethyl)-2,3-Dihydrothiazoles from α-Enolic Dithioesters and Imidoyl Sulfoxonium Ylides
Yang, Dezhi
Wang, Yan
Wang, Taimin
Dou, Qian
Zhou, Kang
Zhai, Hongbin
Cheng, Bin
ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (01) : 88 - 95
[26] Synthesis of Pyrazolo[1,2-a]cinnolines via Rhodium(III)-Catalyzed [4+2] Annulation Reactions of Pyrazolidinones with Sulfoxonium Ylides
Hu, Shulei
Han, Xu
Xie, Xiong
Fang, Feifei
Wang, Yong
Saidahmatov, Abdusaid
Liu, Hong
Wang, Jiang
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (13) : 3311 - 3317
[27] Synthesis of N-Aryl-4-trifluoromethylthiazol-2-amines via Insertion/Annulation of Trifluoromethylimidoyl Sulfoxonium Ylides with Sodium Thiocyanate
Ding, Yuhao
Liu, Yaopeng
Ge, Jin
Wu, Xi
Li, Zhenghao
Cheng, Guolin
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (17): : 12255 - 12262
[28] Formal intermolecular [4+1] cycloaddition reaction of in situ generated ortho-quinomethanes with CF3-Imidoyl sulfoxonium ylides and dual double bond isomerization cascade: Synthesis of trifluoromethyl-containing benzofuran derivatives
Wei, Youyan
Lin, Chao
Li, Bo
Zhang, Yixing
Xu, Shuzhou
TETRAHEDRON, 2025, 173
[29] Rh(III)-Catalyzed [4+2] Annulation of Indoles with Sulfoxonium Ylides for the Synthesis of Dihydropyrimidoindolone Derivatives
Shu, Sai
Huang, Zhibin
Chen, Yujie
Yang, Shan
Jiang, Yaqiqi
Zhang, Jingyu
Zhao, Yingsheng
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (08) : 3171 - 3179
[30] Rh(III)-Catalyzed Cascade Cyclization of 2-Aryl-3H-indoles and CF3-Imidoyl Sulfoxonium Ylides Toward Trifluoroacetimidoyl-Substituted 11H-Isoindolo[2,1-a]indoles
Yang, Zuguang
Li, Pinyi
Chen, Zhengkai
Wu, Xiao-Feng
ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (22) : 3855 - 3860

← 1 2 3 4 5 →