- Condensation-Driven Assembly of Boron-Containing Bis(Heteroaryl) Motifs Using a Linchpin Approach
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Herein, we describe the bromomethyl acyl boronate linchpin-an enabling reagent for the condensation-driven assembly of novel bis(heteroaryl) motifs. This building block is readily accessible from commercially available starting materials. A variety of 2-a
- Adachi, Shinya,Liew, Sean K.,Lee, C. Frank,Lough, Alan,He, Zhi,Denis, Jeffrey D. St.,Poda, Gennady,Yudin, Andrei K.
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- 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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supporting information
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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supporting information
(2021/08/13)
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- Solvent and catalyst-free synthesis of imidazo[1,2-a]pyridines by grindstone chemistry
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The present work describes the solvent and catalyst-free synthesis of imidazo[1,2-a]pyridines in excellent to nearly quantitative yields from 2-aminopyridines and a wide variety of ω-bromomethylketones using a grindstone procedure at 25°C to 30°C for 3 to
- Godugu, Kumar,Nallagondu, Chinna Gangi Reddy
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p. 250 - 259
(2020/10/23)
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- Metal-free, Tf2NH-catalyzed 1, 6-conjugate addition of imidazopyridine to para-quinone methides: Easy access to C3-functionalized triarylmethane imidazopyridine
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An inexpensive and commercially available Tf2NH-catalyzed 1,6-conjugate addition of imidazopyridine (IMPY) heterocycles to para-quinone methides (p-QMs) is reported. The present transformation provides a diverse class of C3-functionalized triarylmethanes heterocyclic derivatives of imidazopyridine. These metal-free transformations provided a very broad substrate scope of conjugate addition product with a high yield up to 97% within a short duration.
- Khonde, Nilesh S.,Said, Madhukar S.,Sabane, Jagjivan K.,Gajbhiye, Jayant M.,Kumar, Pradeep
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supporting information
(2021/10/30)
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- Micellar Catalysis: Visible-Light Mediated Imidazo[1,2-a]pyridine C—H Amination with N-Aminopyridinium Salt Accelerated by Surfactant in Water
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A light-promoted metal-free protocol for the amination of imidazo[1,2-a]pyridines with N-aminopyridinium salt by the assistance of surfactants in water was reported, charactering mild and environmentally benign conditions, as well as great functional grou
- Yang, Zhonglie,Cao, Kun,Peng, Xiaoyan,Lin, Li,Fan, Danchen,Li, Jun-Long,Wang, Jingxia,Zhang, Xiaobin,Jiang, Hezhong,Li, Jiahong
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supporting information
p. 3347 - 3352
(2021/10/20)
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- A simple and efficient route to 2-arylimidazo[1,2-a]pyridines and zolimidine using automated grindstone chemistry
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A green and efficient mechanochemical method for the synthesis of a series of 2-arylimidazo[1,2-a]pyridines was developed using an electrical grinder. I2 catalyzed mechanochemical grinding facilitates the cyclocondensation reaction between various aryl methyl ketones and 2-aminopyridines to afford 2-arylimidazo[1,2-a]pyridines in good yields at ambient temperature. The method was successfully used for the gram-scale synthesis of a marketed drug, zolimidine. The noticeable advantages of this environmentally sustainable protocol include mild conditions, simple instrumentation, inexpensive catalyst, atom economy, short reaction time etc.
- Das, Dharmendra,Bhutia, Zigmee T.,Panjikar, Padmini C.,Chatterjee, Amrita,Banerjee, Mainak
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supporting information
p. 4099 - 4107
(2020/09/09)
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- PhI(OAc)2-mediated oxidative C[sbnd]H sulfoximination of imidazopyridines under mild conditions
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A facile protocol for direct oxidative C[sbnd]N bond coupling of unactivated imidazo[1,2-a]pyridines with NH-sulfoximines was disclosed using sulfoximines as the nitrogen sources in the presence of (diacetoxy)iodobenzene (PhI(OAc)2). The reacti
- Luan, Nannan,Liu, Zhenwei,Han, Shuaijun,Shen, Linhua,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng
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supporting information
(2019/11/26)
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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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- Metal-Free Regioselective Alkylation of Imidazo[1,2- a ]pyridines with N -Hydroxyphthalimide Esters under Organic Photoredox Catalysis
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A visible-light-induced direct C-H alkylation of imidazo[1,2- a ]pyridines has been developed. It proceeds at room temperature by employing inexpensive Eosin Y as a photocatalyst and alkyl N -hydroxyphthalimide (NHP) esters as alkylation reagents. A varie
- Jin, Can,Sun, Bin,Xu, Min,Xu, Tengwei,Yang, Jin,Zhang, Liang,Zhu, Rui
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supporting information
p. 363 - 368
(2020/02/27)
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- SELECTIVE LIGANDS OF HUMAN CONSTITUTIVE ANDROSTANE RECEPTOR
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The present invention provides a structurally novel class of heterocyclic compounds of general formula I wherein L1 is heteroaryl and L2 is heteroaryl or aryl. The novel compounds are useful in a method of prevention or treatment of a condition which is m
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Page/Page column 17-18
(2020/11/12)
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- One-pot NBS-promoted synthesis of imidazoles and thiazoles from ethylarenes in water
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A facile and eco-friendly method has been developed for the synthesis of imidazoles and thiazoles from ethylarenes in water. The reaction proceeds via in situ formation of α-bromoketone using NBS as a bromine source as well as an oxidant, followed by trapping with suitable nucleophiles to provide the corresponding products in good yields under metal-free conditions.
- Chen, Liang,Zhu, Huajian,Wang, Jiang,Liu, Hong
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- Electrochemically initiated intermolecular C-N formation/cyclization of ketones with 2-aminopyridines: An efficient method for the synthesis of imidazo[1,2-: A] pyridines
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Electrochemical intermolecular C-N formation/cyclization of ketones with 2-aminopyridines using catalytic hydriodic acid as the redox mediator was developed, providing imidazo[1,2-a]pyridines under more environmentally benign conditions. The reaction proceeds in a simple undivided cell, using low toxic ethanol as the solvent, without external oxidants, and exhibits high atom economy. A variety of ketones including acetophenones, unsatruated and alkyl ketones are amenable to this reaction, affording the corresponding products in moderate to excellent yields. A three-component tandem reaction realizing C-N, C-S/C-Se bond formation can also be achieved under standard conditions.
- Feng, Mei-Lin,Li, Shu-Qi,He, Hui-Zi,Xi, Long-Yi,Chen, Shan-Yong,Yu, Xiao-Qi
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supporting information
p. 1619 - 1624
(2019/04/08)
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- Sodium Salts (NaI/NaBr/NaCl) for the Halogenation of Imidazo-Fused Heterocycles
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We report herein an effective method for the halogenation of imidazo-fused heterocycles using readily available sodium salts (NaCl/NaBr/NaI) as halogen source and K2S2O8 (or) oxone as promoter. A variety of C-3 halogenated imidazo[1,2-a]pyridines and benzo[d]imidazo[2,1-b]thiazoles were obtained in good to excellent yields. The present method of halogenation has been also extended to 2-aminopyridines, 2-aminopyrimidine, indole, and isoquinoline with moderate to excellent yields.
- Semwal, Rashmi,Ravi, Chitrakar,Kumar, Rahul,Meena, Ramavatar,Adimurthy, Subbarayappa
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p. 792 - 805
(2019/01/24)
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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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supporting information
p. 49 - 52
(2019/01/04)
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- Transition-Metal-Free Direct Trifluoromethylation and Perfluoroalkylation of Imidazopyridines under Mild Conditions
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The first transition-metal-free method for direct C?H trifluoromethylation of imidazo[1,2-a]pyridine derivatives with readily available Ruppert-Prakash reagent TMSCF3 under mild conditions was described. Moreover, this method could be applied to direct C?H perfluoroalkylation of imidazopyridines, affording a series of novel perfluoroalkylated products in moderate to good yields. Notable advantages of this protocol include easy operation, high-efficiency and wide substrate scope. (Figure presented.).
- Han, Shuaijun,Gao, Xianying,Wu, Qingsong,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng
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supporting information
p. 1559 - 1563
(2019/02/19)
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- Exogenous-oxidant-free electrochemical oxidative C-H phosphonylation with hydrogen evolution
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We herein report a versatile and environmentally friendly electrochemical oxidative C-H phosphonylation protocol. This protocol features a broad substrate scope; not only C(sp2)-H phosphonylation, but also C(sp3)-H phosphonylation is tolerated well under exogenous-oxidant-free and metal catalyst-free electrochemical oxidation conditions.
- Yuan, Yong,Qiao, Jin,Cao, Yangmin,Tang, Jingmei,Wang, Mengqin,Ke, Guojuan,Lu, Yichen,Liu, Xue,Lei, Aiwen
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supporting information
p. 4230 - 4233
(2019/04/30)
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- Formation of Methylene Linkage for N-Heterocycles: Sequential C-H and C-O Bond Functionalization of Methanol with Cosolvent Water
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An iron-catalyzed methylene forming strategy is disclosed through sequential C-H and C-O bond functionalization of methanol with cosolvent water. This protocol provides an easy and novel access to methylene-tethered imidazo[1,2-a]pyridine and 2-aminopyridine analogues in a sustainable manner and represents a complementary approach to traditional methylene forming strategies.
- Li, Na,Bai, Jinku,Zheng, Xiaolin,Rao, Honghua
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p. 6928 - 6939
(2019/06/14)
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- 2-PHENYL-3-(PIPERAZINOMETHYL)IMIDAZO[1,2-A]PYRIDINE DERIVATIVES AS BLOCKERS OF TASK-1 AND TASK-2 CHANNELS, FOR THE TREATMENT OF SLEEP-RELATED BREATHING DISORDERS
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The present application relates to novel 2-phenyl-3-(piperazinomethyl)imidazo[1,2-a]pyridine derivatives, to processes for their preparation, to their use alone or in combinations for the treatment and/or prevention of diseases, and to their use for prepa
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Paragraph 0352-0355
(2019/03/08)
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- SUBSTITUTED PERHYDROPYRROLO[3,4-C]PYRROLE DERIVATIVES AND THE USE OF SAME
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The present application relates to novel (2-phenylimidazo[1,2-a]pyridin-3-yl)methyl-substituted perhydropyrrolo[3,4-c]pyrrole derivatives, to methods for the preparation thereof, to the use thereof alone or in combinations for treatment and/or prevention
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Paragraph 0410-0413; 0414
(2019/01/09)
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- Synthesis and Optical Properties of Push–Push–Pull Chromophores Based on Imidazo[5,1,2-cd]indolizines and Naphtho[1′,2′:4,5]imidazo[1,2-a]pyridines
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Four series of new push–push–pull chromophores based on two types of heterocyclic cores, namely imidazo[5,1,2-cd]indolizines and naphtho[1′,2′:4,5]imidazo[1,2-a]pyridines, and two types of linear π spacers, namely diphenylacetylene and biphenyl, were prep
- Maitra, Ratnava,Chen, Jie-Hong,Hu, Ching-Han,Lee, Hon Man
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p. 5975 - 5985
(2017/11/14)
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- Easy and efficient selenocyanation of imidazoheterocycles using triselenodicyanide
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The regioselective selenocyanation of imidazoheterocycles using triselenodicyanide at room temperature is reported. The electrophilic aromatic substitution of a broad range of substrates is promoted by the triselenodicyanide obtained by oxidative coupling
- Redon, Sébastien,Obah Kosso, Anne Roly,Broggi, Julie,Vanelle, Patrice
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supporting information
p. 2771 - 2773
(2017/06/23)
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- Solvent- and catalyst-free synthesis of imidazo[1,2-a]pyridines under microwave irradiation
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A facile solvent- and catalyst-free method for the synthesis of a series of imidazo[1,2-a]pyridines in good to excellent yields by the condensation of 2-aminopyridines with α-bromoketones under microwave irradiation has been developed. The important featu
- Kong, Dulin,Wang, Xianghui,Shi, Zaifeng,Wu, Mingshu,Lin, Qiang,Wang, Xin
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p. 529 - 531
(2016/10/05)
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- KINASE INHIBITORS AND THEIR USE IN CANCER THERAPY
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The present invention relates to a 2,3-diphenyl-1,6-naphthyridine-5-one derivative according to general formula (I), and the use of the 2,3-diphenyl-1,6-naphthyridine-5-one derivative in the diagnosis or treatment of cancer.
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- Covalent-Allosteric Kinase Inhibitors
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Targeting and stabilizing distinct kinase conformations is an instrumental strategy for dissecting conformation-dependent signaling of protein kinases. Herein the structure-based design, synthesis, and evaluation of pleckstrin homology (PH) domain-depende
- Weisner, J?rn,Gontla, Rajesh,Van der westhuizen, Leandi,Oeck, Sebastian,Ketzer, Julia,Janning, Petra,Richters, Andr,Mühlenberg, Thomas,Fang, Zhizhou,Taher, Abu,Jendrossek, Verena,Pelly, Stephen C.,Bauer, Sebastian,Van otterlo, Willem A. L.,Rauh, Daniel
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p. 10313 - 10316
(2015/09/01)
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- Heterogeneously copper-catalyzed oxidative synthesis of imidazo[1,2-a]pyridines using 2-aminopyridines and ketones under ligand- and additive-free conditions
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An efficient and mild heterogeneously CuCl2/nano-TiO 2-catalyzed aerobic synthesis of imidazo[1,2-a]pyridines from 2-aminopyridines and ketones has been developed using air as the oxidant in the absence of any ligands and additives. This strategy was compatible with a large range of substrates, including unactivated aryl ketones and unsaturated ketones and went through the C-H bond functionalization mechanism instead of I --assisted Ortoleva-King reaction to provide the corresponding imidazo[1,2-a]pyridines in good yields with low catalyst loading (0.8 mol%). Moreover, the heterogeneous catalyst can be successfully employed in gram-scale synthesis and reused many times without the significant loss of catalytic activity.
- Meng, Xu,Wang, Yanmin,Yu, Chaoying,Zhao, Peiqing
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p. 27301 - 27307
(2014/07/21)
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- Iron(III)-catalyzed denitration reaction: One-pot three-component synthesis of imidazo[1,2-a]pyridine derivatives
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An iron(III)-catalyzed one-pot three-component cross-coupling nitration reaction of 2-aminopyridines, aldehydes and nitroalkanes, straightforwardly forms imidazo[1,2-a]pyridine derivatives and is described in this report. The system shows good functional-group tolerance and proceeds smoothly in moderate to good yields. An iron(III)-catalyzed one-pot three-component cross-coupling nitration reaction of 2-aminopyridines, aldehydes, and nitroalkane, leading to the straightforward formation of imidazo[1,2-a]pyridine derivatives has been reported. In this procedure, the starting materials are commercially available. The system shows good functional-group tolerance and proceeds smoothly in moderate to good yields. Copyright
- Yan, Hao,Wang, Yuling,Pan, Congming,Zhang, Hao,Yang, Sizhuo,Ren, Xiaoyu,Li, Jian,Huang, Guosheng
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p. 2754 - 2763
(2014/05/06)
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- Copper-catalyzed aerobic oxidative C-H functionalization of substituted pyridines: Synthesis of imidazopyridine derivatives
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A novel, efficient, and practical method for the synthesis of imidazopyridine derivatives has been developed through the copper-catalyzed aerobic oxidative C-H functionalization of substituted pyridines with N-(alkylidene)-4H-1,2,4-triazol-4-amines. The procedure occurs by cleavage of the N-N bond in the N-(alkylidene)-4H-1,2,4-triazol-4-amines and activation of an aryl C-H bond in the substituted pyridines. This is the first example of the preparation of imidazopyridine derivatives by using pyridines as the substrates by transition-metal-catalyzed C-H functionalization. This method should provide a novel and efficient strategy for the synthesis of other nitrogen heterocycles.
- Yu, Jipan,Jin, Yunhe,Zhang, Hao,Yang, Xiaobo,Fu, Hua
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supporting information
p. 16804 - 16808
(2014/01/06)
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- CuI-catalyzed aerobic oxidative α-aminaton cyclization of ketones to access aryl or alkenyl-substituted imidazoheterocycles
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CuI-catalyzed aerobic oxidative synthesis of imidazoheterocycles has been achieved. Four hydrogen atoms were removed in one step. This protocol was compatible with a broad range of functional groups, and it has been also successfully extended to unsaturated ketones, bringing about the formation of alkenyl-substituted imidazoheterocycles, which were difficult to prepare by previous means. Preliminary mechanistic studies indicated that this reaction was most likely to proceed through a catalytic Ortoleva-King reaction. By using this method, the marketed drug Zolimidine could be prepared with 90% yield on a gram scale from commercially available materials.
- Zhang, Yuhong,Zhang, Yuanfei,Chen, Zhengkai,Wu, Wenliang,Su, Weiping
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supporting information
p. 12494 - 12504
(2014/01/17)
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- Regioselective synthesis of 2- and 3-substituted imidazo[1,2-a]pyridines
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A range of 2- or 3-substituted imidazo[1,2-a]pyridines were prepared from 2-aminopyridine derivatives and gemdibromovinyl compounds by the tandem nucleophilic substitution (or nucleophilic addition)/cyclisation reaction.
- Liu, Guoping,Cong, Xuefeng,He, Jiaheng,Luo, Shunzhong,Wu, Di,Lan, Jingbo
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p. 687 - 690
(2013/02/23)
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- DIAGNOSTIC AND REMEDY FOR DISEASE CAUSED BY AMYLOID AGGREGATION AND/OR DEPOSITION
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To provide a diagnostic drug which binds specifically to an amyloid aggregate and/or an amyloid deposit, to thereby realize imaging and quantification of a disease caused by amyloid aggregation and/or deposition. The invention provides a compound represented by formula (1) : (wherein X1 represents an optionally substituted bicyclic heterocyclic group; X2 represents a hydrogen atom, a halogen atom, or a chelate-forming group; ring A represents a benzene ring or a pyridine ring; and ring B represents an optionally substituted 5-membered aromatic heterocyclic group which is bonded to the benzene ring or the pyridine ring via a carbon atom of ring B), a salt thereof, a solvate of any of these, or a transition metal coordination compound of any of these, and a diagnostic, preventive, or therapeutic drug containing the same.
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Page/Page column 42
(2008/12/07)
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- Bis-cationic heteroaromatics as macrofilaricides: Synthesis of Bis- amidine and bis-guanylhydrazone derivatives of substituted imidazol[1,2- a]pyridines
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A series of guanylhydrazone, amidine, and hydrazone derivatives of 2- phenylimidazo[1,2-a]-pyridine have been prepared and evaluated for macrofilarial activity against Acanthocheilonema viteae and Brugia pahangi in jirds. Compounds with 4',6-bis-substitut
- Sundberg, Richard J.,Biswas, Sujay,Murthi, Krishna Kumar,Rowe, Donna,McCall, John W.,Dzimianski, Michael T.
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p. 4317 - 4328
(2007/10/03)
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