131947-30-3Relevant academic research and scientific papers
Graphene oxide (GO)-catalyzed multi-component reactions: Green synthesis of library of pharmacophore 3-sulfenylimidazo[1,2-a]pyridines
Kundu, Samir,Basu, Basudeb
, p. 50178 - 50185 (2015)
The green carbocatalyst graphene oxide (GO) has been successfully utilized for selective and expedient synthesis of biologically important motifs imidazo[1,2-a]pyridines, and 3-sulfenylimidazo[1,2-a]pyridines via one-pot multi-component reactions (MCR). D
Ammonium Iodide Induced Nonradical Regioselective Sulfenylation of Flavones via a C-H Functionalization Process
Zhao, Wannian,Xie, Ping,Bian, Zhaogang,Zhou, Aihua,Ge, Haibo,Zhang, Min,Ding, Yingcai,Zheng, Lian
, p. 9167 - 9175 (2015)
A novel and highly regioselective ammonium iodide-induced nonradical sulfenylation method for the construction of a C-S bond was developed via C-H functionalization. With DMSO or R1SO2NHNH2 as a sulfenylating agent, MeS- and R1S-substituted flavone derivatives were obtained in good yields. This method enriches current C-S bond formation chemistry, making it a highly valuable and practical method in pharmaceutical industry.
Generation of thioethers via direct C-H functionalization with sodium benzenesulfinate as a sulfur source
Ding, Yingcai,Wu, Wei,Zhao, Wannian,Li, Yiwen,Xie, Ping,Huang, Youqin,Liu, Yu,Zhou, Aihua
, p. 1428 - 1431 (2016)
A novel ammonium iodide-induced sulfenylation method of flavones, indole and arylimidazo[1,2-a]pyridines using stable and odorless sodium benzenesulfinates as sulfur sources was developed, generating regioselective derivatives in good yields. This method has enriched current thioether-producing methods and provided a good example of using ammonium iodide as a reaction inducer instead of iodine to make thioethers under environmentally friendly and odorless conditions.
KOH-mediated intramolecular amidation and sulfenylation: A direct approach to access 3-(arylthio)imidazo[1,2-a]pyridin-2-ols
Pandey, Khima,Shinde, Vikki N.,Rangan, Krishnan,Kumar, Anil
, (2020)
A simple and facile method for the synthesis of 3-(arylthio)imidazo[1,2-a]pyridin-2-ols has been developed by a KOH-mediated reaction of 2-aminopyridinium bromides with aryl thiols. The method afforded a wide range of 3-(arylthio)imidazo[1,2-a]pyridin-2-ols in moderate to excellent (56–95%) yields with excellent functional group tolerance. Synthetic utility of the protocol was demonstrated by gram-scale reaction and preparation of 2-aryl-3-(p-tolylthio)imidazo[1,2-a]pyridines from 3-(p-tolylthio)imidazo[1,2-a]pyridin-2-ol.
Iodine-Mediated Sulfenylation of Imidazo[1,2- a ]pyridines with Ethyl Arylsulfinates
Sun, Jian,Mu, Yangxiu,Iqbal, Zafar,Hou, Jing,Yang, Minghua,Yang, Zhixiang,Tang, Dong
supporting information, p. 1014 - 1018 (2021/03/15)
A simple iodine-mediated approach is reported for the synthesis of sulfenylated imidazo[1,2- a ]pyridines through the reaction of imidazo[1,2- a ]pyridines with ethyl arylsulfinates under mild conditions. The reaction scope was investigated, and a plausible mechanism is proposed to elucidate the reaction process and activation mode. The results indicate that ethyl sulfinates are efficient sulfur sources for the construction of C-S bonds.
Multicomponent Synthesis of Imidazo[1,2- a]pyridines: Aerobic Oxidative Formation of C-N and C-S Bonds by Flavin-Iodine-Coupled Organocatalysis
Okai, Hayaki,Tanimoto, Kazumasa,Ohkado, Ryoma,Iida, Hiroki
supporting information, p. 8002 - 8006 (2020/11/02)
Herein, we report an aerobic oxidative C-N bond-forming process that enables the facile synthesis of imidazo[1,2-a]pyridines and takes advantage of a coupled organocatalytic system that uses flavin and iodine. Furthermore, the dual catalytic system can be applied to the one-pot, three-step synthesis of 3-thioimidazo[1,2-a]pyridines from aminopyridines, ketones, and thiols.
Electrochemically enabled synthesis of sulfide imidazopyridines: via a radical cyclization cascade
Lin, Hong-Min,Meng, Xiu-Jin,Mo, Zu-Yu,Pan, Ying-Ming,Tang, Hai-Tao,Wang, Lin-Wei,Zhong, Ping-Fu
supporting information, p. 6334 - 6339 (2020/11/09)
Owing to the inert nature of the pyridine ring and high activity of iminyl radicals, the reaction between pyridine and iminyl radicals remains a significant challenge. In this paper, we report the synthesis of sulfide imidazo[1,2-a]pyridines from vinyl azides, thiophenols, and pyridines via a radical [3 + 2] cycloaddition. Promoting inert pyridine and highly active iminyl radicals to participate in this intermolecular cycloaddition process is the striking feature of this protocol. The excellent antitumor activity of the prepared sulfide imidazopyridine scaffold demonstrated the synthetic utility of the developed synthetic protocol.
Unconventional Reactivity with DABCO-Bis(sulfur dioxide): C–H Bond Sulfenylation of Imidazopyridines
Le Bescont, Julie,Breton-Patient, Chloé,Piguel, Sandrine
, p. 2101 - 2109 (2020/04/07)
This work highlights the unexpected and unprecedented outcome of the reactivity with DABCO-bis(sulfur dioxide). The use of this reagent led to the exclusive introduction of a sulfur atom on the C-3 position of imidazopyridines instead of a sulfone group.
One-pot synthesis of imidazo[1,2-α]pyridine thioethers using imidazo[1,2-α]pyridines, arylsulfonyl chlorides and hydrazine
Wang, Jin,Zhu, Jie,Zhou, Aihua
, p. 256 - 262 (2020/01/02)
A one-pot reaction of making RS-substituted imidazo[1,2-α]pyridine derivatives by directly using aryl or alkylsulfonyl chloride and hydrazine was developed, selectively giving good yields of the expected products. Compared with previously reported methods
Iodine-Mediated Multicomponent Synthesis of 3-Sulfenylimidazo[1,2- a ]pyridines from 2-Aminopyridines, Ketones, and Sulfonyl Hydrazides
Hu, Sipei,Du, Shiying,Yao, Yunjie,Yang, Zuguang,Ren, Hongjun,Chen, Zhengkai
supporting information, p. 625 - 629 (2019/03/07)
A one-pot multicomponent reaction for the synthesis of 3-sulfenylimidazo[1,2- a ]pyridines from readily available 2-aminopyridines, ketones, and sulfonyl hydrazides, mediated by molecular iodine, has been developed. The transformations proceed smoothly wi
