- Iodine-Mediated Sulfenylation of Imidazo[1,2- a ]pyridines with Ethyl Arylsulfinates
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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.
- Sun, Jian,Mu, Yangxiu,Iqbal, Zafar,Hou, Jing,Yang, Minghua,Yang, Zhixiang,Tang, Dong
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p. 1014 - 1018
(2021/03/15)
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- Design, synthesis and anticancer activity of sulfenylated imidazo-fused heterocycles
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We report herein, the design, synthesis and study of anticancer properties of sulfenylated 2-phenylimidazo[1,2-a]pyridines and their analogues. A set of twenty sulfenylated imidazo[1, 2-a]pyridine derivatives were synthesized. Whereby elusive amendments to the imidazo[1,2-a]pyridine motif confer dramatic changes in functional affinity of a novel action to modulate anticancer activity in seven different human cancer cell lines i.e.: MDA MB 231 (breast), HepG2 (liver), Hela (cervical), A549 (lung), U87MG (glioblastoma), SKMEL-28 (skin melanoma) and DU-145 (prostate) by employing MTT assay. Among the series, compounds 4e (naphthalene), 4f (styrene) and 4h (thiomethyl) showed potent activity towards human liver cancer cells HepG2. Cell cycle analysis results revealed that these compounds arrested the cell cycle at G2/M phase and induced apoptosis in human liver cancer cells HepG2. It was further confirmed by Hoechst staining, Measurement of mitochondrial membrane potential (ΔΨm) and Annexin V-FITC assay.
- Chitrakar, Ravi,Rawat, Deepa,Sistla, Ramakrishna,Subbarayappa, Adimurthy,Vadithe, Lakshma Nayak
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- Unconventional Reactivity with DABCO-Bis(sulfur dioxide): C–H Bond Sulfenylation of Imidazopyridines
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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.
- Le Bescont, Julie,Breton-Patient, Chloé,Piguel, Sandrine
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p. 2101 - 2109
(2020/04/07)
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- One-pot synthesis of imidazo[1,2-α]pyridine thioethers using imidazo[1,2-α]pyridines, arylsulfonyl chlorides and hydrazine
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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
- Wang, Jin,Zhu, Jie,Zhou, Aihua
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p. 256 - 262
(2020/01/02)
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- S-Aryl Arenesulfonothioate and Copper Acetate Mediated Arylthiolation of 2-Arylpyridines and Heteroarenes
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Copper acetate mediated regioselective ortho-arylthiolation of 2-arylpyridines has been accomplished for the first time using S-aryl arenesulfonothioate as the arylthiolating agent. The reaction shows good functional group tolerance and gives thioarylated products in 67-89% yields. This reagent is a good alternative to unpleasant smelling arylthiols. Experimental evidence suggests an unprecedented insertion of an arylthio unit from both parts of the reagent (SPh and p-TolSO2) in the presence of copper acetate. Indoles and imidazopyridines also undergo facile reaction at the C-3 position and furnish thioarylated derivatives in good yields.
- Sharma, Poonam,Jain, Nidhi
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p. 13045 - 13052
(2019/10/11)
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- Iodine-Mediated Multicomponent Synthesis of 3-Sulfenylimidazo[1,2- a ]pyridines from 2-Aminopyridines, Ketones, and Sulfonyl Hydrazides
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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
- Hu, Sipei,Du, Shiying,Yao, Yunjie,Yang, Zuguang,Ren, Hongjun,Chen, Zhengkai
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supporting information
p. 625 - 629
(2019/03/07)
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- Method for synthesizing 3-bit sulfenyl substituted imidazo [1, 2-a] pyridine compound by molecular iodine promotion one-pot method
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The invention discloses a method for synthesizing a 3-bit sulfenyl substituted imidazo [1, 2-a] pyridine compound by a molecular iodine promotion one-pot method. The method comprises the following steps that molecular iodine, triphenylphosphine, 2-aminopy
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Paragraph 0042; 0043; 0044; 0045; 0049; 0050; 0070; 0071
(2019/02/04)
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- Electrochemical Oxidative C—H Sulfenylation of Imidazopyridines with Hydrogen Evolution
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Selective oxidative C—H sulfenylation of imidazopyridine heterocycles is achieved using an undivided electrolytic cell. The reaction avoids the use of stoichiometric amount of external chemical oxidant and produces hydrogen gas as the only byproduct. Both
- Yuan, Yong,Cao, Yangmin,Qiao, Jin,Lin, Yueping,Jiang, Xiaomei,Weng, Yaqing,Tang, Shan,Lei, Aiwen
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- Metal-free direct regioselective thiolation of imidazoheterocycles in water at room temperature
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A metal-free direct thiolation of imidazoheterocycles with various thiophenol in water at room temperature has been developed. In addition, the chemistry provides several advantages including mild condition, high yields, good functional group tolerance, g
- Kong, Dulin,Wang, Qinghe,Huang, Tiao,Liang, Min,Lin, Qiang,Wu, Mingshu
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supporting information
p. 1457 - 1463
(2019/02/06)
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- Cobalt-Catalyzed Aerobic Cross-Dehydrogenative Coupling of C-H and Thiols in Water for C-S Formation
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Organosulfides have great significance and value in synthetic and biological chemistry. To establish a versatile and green methodology for C-S bond generation, we successfully developed a new aerobic cross-dehydrogenative coupling of C-H and S-H to synthe
- Huang, Xin,Chen, Yongqi,Zhen, Shan,Song, Lijuan,Gao, Mingqi,Zhang, Panke,Li, Heng,Yuan, Bingxin,Yang, Guanyu
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p. 7331 - 7340
(2018/07/29)
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- Copper-catalyzed three-component reaction of imidazo[1,2-a]pyridine with elemental sulfur and arylboronic acid to produce sulfenylimidazo[1,2-a]pyridines
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In this work, an efficient copper-catalyzed three-component reaction for the synthesis of sulfenylimidazo[1,2-a]pyridines using elemental sulfur as the sulfenylating agents has been developed. The reaction could proceed smoothly with a high degree of functional group tolerance and provide the desired products in moderate to good yield.
- Xiao, Genhua,Min, Hao,Zheng, Zhilei,Deng, Guobo,Liang, Yun
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supporting information
p. 1363 - 1366
(2018/01/08)
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- Iodine-Mediated Difunctionalization of Imidazopyridines with Sodium Sulfinates: Synthesis of Sulfones and Sulfides
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Novel iodine-induced sulfonylation and sulfenylation of imidazopyridines have been described using sodium sulfinates as the sulfur source. This strategy enables highly selective difunctionalization of imidazo[1,2-a]pyridine to access sulfones and sulfides in good yields. A wide range of substrates and functional groups were well-tolerated under optimized conditions. Moreover, control experiments have been conducted, indicating a radical pathway involved in the reaction mechanisms.
- Guo, Yu-Jing,Lu, Shuai,Tian, Lu-Lu,Huang, En-Ling,Hao, Xin-Qi,Zhu, Xinju,Shao, Tian,Song, Mao-Ping
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p. 338 - 349
(2018/02/19)
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- Visible-light-induced regioselective sulfenylation of imidazopyridines with thiols under transition metal-free conditions
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A metal-free visible-light-promoted regioselective C-3 sulfenylation of imidazo[1,2-a]pyridines and indoles using thiols has been developed via C(sp2)-H functionalization. This method provides direct access to a wide range of structurally diver
- Rahaman, Rajjakfur,Das, Shivasish,Barman, Pranjit
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supporting information
p. 141 - 147
(2018/01/12)
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- Tandem Flavin-Iodine-Catalyzed Aerobic Oxidative Sulfenylation of Imidazo[1,2- a]Pyridines with Thiols
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A green, aerobic sulfenylation of imidazo[1,2-a]pyridines was performed using thiols, a flavin-and-iodine dual catalytic system, and environmentally benign molecular oxygen as the only sacrificial reagent. The dual metal-free catalysts smoothly promote a unique stepwise tandem process, beginning with the aerobic oxidation of a thiol to afford a disulfide that is utilized in the oxidative sulfenylation of the imidazo[1,2-a]pyridine. This process has afforded diverse 3-sulfenylimidazo[1,2-a]pyridines of biological interest and is environmentally friendly, as benign H2O is the only byproduct.
- Iida, Hiroki,Demizu, Ryuta,Ohkado, Ryoma
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p. 12291 - 12296
(2018/09/27)
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- NH4I-catalyzed chalcogen(S/Se)-functionalization of 5-membered N-heteroaryls under metal-free conditions
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Herein, we described the NH4I-catalyzed C–H bond chalcogenation of N-heteroaryls in the presence of a minimum amount of DMSO/H2O/acetic acid as additives (2.5/2.5/1 M equiv., respectively), under metal-free conditions. Under optimized conditions, a wide variety of sulfenyl/selenyl imidazo[1,2-α]pyridines were prepared in very good yields. Moreover, the present approach was also highly efficient for the chalcogenation of different 5-membered N-heteroaryls, e.g., indole, imidazothiazole, indazole and imidazopyrimidine derivatives.
- Bettanin, Luana,Saba, Sumbal,Doerner, Carlos V.,Franco, Marcelo S.,Godoi, Marcelo,Rafique, Jamal,Braga, Antonio L.
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p. 3971 - 3980
(2018/06/12)
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- Visible light-induced C-H sulfenylation using sulfinic acids
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The visible light and Eosin B-catalyzed direct sulfenylation of sp2 C-H bonds with sulfinic acids through a photoredox process has been demonstrated at room temperature under transition metal-free conditions for the first time. Diverse heteroaryl sulfides were obtained in moderate to good yields. This is the first example of the sulfenylation of sp2 C-H bonds using arylsulfinic acids as odorless sulfur reagents under visible light-induced conditions. More interestingly, the reductive products could be obtained under visible light-induced oxidative conditions. This protocol demonstrates a new model for C-S bond formation, which serves as a novel approach toward the synthesis of heteroaryl sulfides.
- Sun, Pengfei,Yang, Daoshan,Wei, Wei,Jiang, Min,Wang, Zuli,Zhang, Liyan,Zhang, Hui,Zhang, Zhenzhen,Wang, Yu,Wang, Hua
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supporting information
p. 4785 - 4791
(2017/10/19)
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- C3 Sulfenylation of N-Heteroarenes in Water under Catalyst-Free Conditions
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A method for the catalyst-free C–H sulfenylation of imidazo[1,2-a]pyridines by using sulfonothioates as an odorless thioarylated reagent in aqueous medium was developed. This protocol was used for a variety of substituted imidazo[1,2-a]pyridines with broad functional-group tolerance and was extended to the sulfenylation of indoles and imidazothiazoles. The sulfonothioates were activated exclusively in aqueous medium rather than in an organic solvent, and the feasibility of the process for scale-up studies was demonstrated.
- Ravi, Chitrakar,Joshi, Abhisek,Adimurthy, Subbarayappa
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supporting information
p. 3646 - 3651
(2017/07/22)
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- One-Pot Three-Component Synthesis of Alkylthio-/Arylthio- Substituted Imidazo[1,2-a]pyridine Derivatives via C(sp2)–H Functionalization
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Sulfenylation is an important transformation to generate C?S bonds in organic synthesis. Here, two three-component synthetic protocols have been developed by using imidazo[1,2-a]pyridine, inorganic, odorless S8 and alcohols or arylboronic acids
- Zhu, Wenhui,Ding, Yingcai,Bian, Zhaogang,Xie, Ping,Xu, Baojun,Tang, Qiujie,Wu, Wei,Zhou, Aihua
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p. 2215 - 2221
(2017/07/07)
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- Dual role of p-tosylchloride: Copper-catalyzed sulfenylation and metal free methylthiolation of imidazo[1,2-a]pyridines
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Copper-catalyzed regioselective C-3 sulfenylation of imidazo[1,2-a]pyridines using p-tosylchloride as a benign source of sulfenylating agents has been developed. On the other hand, p-tosylchloride mediated thiomethylation of imidazo[1,2-a]pyridines with dimethylsulfoxide as a source of thiomethylation under metal-free conditions was also described.
- Ravi, Chitrakar,Chandra Mohan, Darapaneni,Adimurthy, Subbarayappa
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p. 2282 - 2290
(2016/03/01)
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- Generation of thioethers via direct C-H functionalization with sodium benzenesulfinate as a sulfur source
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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.
- Ding, Yingcai,Wu, Wei,Zhao, Wannian,Li, Yiwen,Xie, Ping,Huang, Youqin,Liu, Yu,Zhou, Aihua
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supporting information
p. 1428 - 1431
(2016/02/03)
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- Graphene oxide (GO)-catalyzed multi-component reactions: Green synthesis of library of pharmacophore 3-sulfenylimidazo[1,2-a]pyridines
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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
- Kundu, Samir,Basu, Basudeb
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p. 50178 - 50185
(2015/06/25)
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- Iodine-triphenylphosphine mediated sulfenylation of imidazoheterocycles with sodium sulfinates
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An efficient approach to sulfenyl imidazoheterocycles has been developed via iodine-triphenylphosphine mediated direct sulfenylation of imidazoheterocycles with sodium sulfinates. The reactions proceed smoothly under transition-metal-free conditions with a broad range of substrate scope, giving the desired products in moderate to excellent yields. This journal is
- Huang, Xuhu,Wang, Shucheng,Li, Bowen,Wang, Xin,Ge, Zemei,Li, Runtao
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p. 22654 - 22657
(2015/03/14)
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- N-chlorosuccinimide-promoted regioselective sulfenylation of imidazoheterocycles at room temperature
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Regioselective sulfenylation of imidazoheterocycles with thiophenols at room temperature is reported. Sulfenylation is promoted by N-chlorosuccinimide under metal-free conditions with a broad range of substrate scopes.
- Ravi, Chitrakar,Chandra Mohan, Darapaneni,Adimurthy, Subbarayappa
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supporting information
p. 2978 - 2981
(2014/06/23)
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- Cs2CO3 promoted direct C-H bond sulfenylation of imidazo[1,2-a]pyridines and related heteroarenes in ionic liquid
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An efficient and novel method was developed for the synthesis of 3-sulfenyl imidazo[1,2-a]pyridines in good to excellent yields via a Cs2CO 3 promoted direct sulfenylation of imidazo[1,2-a]pyridines. The reaction proceeds smoothly with a wide range of structurally diverse heteroarenes and disulfides. This protocol is environmentally friendly because it is free of transition-metal catalysts and utilizes aryl-substituted imidazolium-based ionic liquid rather than volatile organic solvents.
- Gao, Zhaochang,Zhu, Xun,Zhang, Ronghua
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p. 19891 - 19895
(2014/05/20)
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- Aerobic multicomponent tandem synthesis of 3-sulfenylimidazo[1,2-a] pyridines from ketones, 2-aminopyridines, and disulfides
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An aerobic CeCl3·7H2O/NaI-catalyzed C-H functionalization reaction was developed for the synthesis of 3-sulfenylimidazo[1,2-a]pyridines from easily available ketones, 2-aminopyridines, and disulfides without DMSO or peroxide as an ox
- Ge, Wenlei,Zhu, Xun,Wei, Yunyang
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supporting information
p. 6015 - 6020
(2013/09/24)
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- An efficient and clean CuI-catalyzed chalcogenylation of aromatic azaheterocycles with dichalcogenides
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A highly efficient and environmentally friendly method for catalytic chalcogenylation of imidazopyridines, imidazopyrimidines, indoles, and pyrrolo[2,3-b]pyridines with dichalcogenides has been developed by using CuI as catalyst under air. The reactions proceed smoothly to give the desired products in moderate to excellent yields, without the presence of other additive.
- Li, Zhen,Hong, Jianquan,Zhou, Xigeng
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supporting information; experimental part
p. 3690 - 3697
(2011/06/17)
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