- Oxidative C-H/C-H Annulation of Imidazopyridines and Indazoles through Rhodium-Catalyzed Vinylene Transfer
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Transition-metal-catalyzed C-H activation followed by oxidative annulation with alkynes has been an efficient synthetic tool for the assembly of various polyaromatic scaffolds. Despite the substantial progress in this field, it is still a significant chal
- Ghosh, Koushik,Nishii, Yuji,Miura, Masahiro
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- Structural Determinants for the Mode of Action of Imidazopyridine DS2 at δ-Containing γ-Aminobutyric Acid Type A Receptors
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Despite the therapeutic relevance of δ-containing γ-aminobutyric acid type A receptors (GABAARs) and the need for δ-selective compounds, the structural determinants for the mode and molecular site of action of δ-selective positive allosteric modulator imi
- Rostrup, Frederik,Falk-Petersen, Christina B.,Harpsoe, Kasper,Buchleithner, Stine,Conforti, Irene,Jung, Sascha,Gloriam, David E.,Schirmeister, Tanja,Wellendorph, Petrine,Frolund, Bente
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p. 4730 - 4743
(2021/05/06)
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- Metal-free oxidative decarbonylative halogenation of fused imidazoles
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An efficient strategy has been developed for the deformylative halogenation of carbaldehyde imidazo-fused heterocycles in the presence of TBHP controlled by temperature. A convenient and sequential functionalization (C8 to C3) portrays the synthetic utility of the current method.N-Heterocycle benzamide products were also observedviathe ring opening of imidazopyridines through the cleavage of C-C bond at high temperatures. Features of this method include temperature-controlled excellent regioselectivity, mild conditions and functional group tolerance.
- Kumar, Gulshan,Shankar, Ravi,Singh, Davinder,Tali, Javeed Ahmad
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p. 20551 - 20555
(2021/11/23)
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- Metal-free regioselective bromination of imidazo-heteroarenes: The dual role of an organic bromide salt in electrocatalysis
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This paper represents an electrochemical transformation by demonstrating the dual role of an organic bromide salt, i.e., tetra-n-butylammonium bromide (TBAB), as a brominating agent and as an electrolyte for the regioselective bromination of several imida
- Raha Roy, Sudipta,Roy, Vishal Jyoti,Sen, Partha Pratim
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supporting information
p. 5687 - 5695
(2021/08/16)
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- Preparation method of C-3 haloimidazolium [1,2-a] pyridine derivative
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The present invention discloses a method for preparing a C-3 haloimidazolium [1,2-a] pyridine derivative, belonging to the field of organic synthesis. The method took imidazolium [1,2-a] pyridine as the starting material, halide cuprous as the halogen sou
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Paragraph 0024-0025
(2022/01/08)
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- Difluorinative-hydroxylation and C-3 functionalization (halogenation/SCN/NO) of imidazopyridine using Selectfluor as fluorine source or oxidant respectively
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An efficient route for the difluorinative-hydroxylation through dearomative difunctionalization of imidazopyridine using Selectfluor as fluorine source has been developed in an aqueous medium. The reaction proceeds through ionic followed by radical pathwa
- Balasubramanian, Sridhar,Kalari, Saradhi,Rode, Haridas B.
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supporting information
(2021/04/15)
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- Ultrasound-Promoted and Base-Mediated Regioselective Bromination of Imidazo[1,2- a ]pyridines with Pyridinium Tribromide
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By using pyridinium tribromide as the bromo source, an efficient- and practical protocol for the synthesis of C3-brominated imidazo-[1,2- a ]pyridines through ultrasound-promoted and Na 2CO 3-mediated regioselective bromination of im
- Jiang, Hongmei,Guo, Dingyi,Zhang, Yixin,Shen, Qin-Peng,Tang, Shiyun,You, Junheng,Huo, Yi,Wang, Huixian,Gui, Qing-Wen
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p. 2713 - 2720
(2020/09/15)
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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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p. 4099 - 4107
(2020/09/09)
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- Electrochemical oxidative iodination of imidazo[1,2-a]pyridines using NaI as iodine source
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An electrochemical oxidative iodination of imidazo[1,2-a]pyridines is achieved in this study. This reaction utilizes NaI as an iodine source and a supporting electrolyte under metal-free and exogenous chemical oxidant-free reaction conditions. The present
- Park, Jin Wha,Kim, Yong Hwan,Kim, Dae Young
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supporting information
p. 710 - 718
(2020/01/31)
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- C3-site halogenation method of 2-phenylimidazo [1, 2-alpha] pyridine compound
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The invention belongs to the technical field of organic synthesis, and specifically relates to a C3 site halogenation method of a 2-phenylimidazo [1, 2-alpha] pyridine compound, and the method comprises the following steps: in an air environment, by using
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Paragraph 0024-0028
(2020/04/22)
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- Visible light-mediated photocatalytic bromination of 2-arylimidazo[1,2-a]pyridines using CBr4 as bromine source
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The photocatalytic bromination of 2-arylimidazo[1,2-a]pyridines is described in this paper. This reaction uses the readily accessible and shelf-stable CBr4 as a bromine source. This photocatalytic system is shown to serve as a convenient and pr
- Lee, Ju Hui,Jung, Hye Im,Kim, Dae Young
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supporting information
p. 197 - 206
(2019/12/03)
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- Trihaloisocyanuric acids in ethanol: an eco-friendly system for the regioselective halogenation of imidazo-heteroarenes
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Herein, we describe an efficient, rapid and benign protocol for the direct C(sp2)-H bond halogenation (Cl, Br, I) of 2-arylimidazo[1,2-a]pyridines using trihaloisocyanuric acids in ethanol. Furthermore, this sustainable protocol was successfull
- Neto, José S. S.,Balaguez, Renata A.,Franco, Marcelo S.,de Sá Machado, Victor C.,Saba, Sumbal,Rafique, Jamal,Galetto, Fábio Z.,Braga, Antonio L.
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supporting information
p. 3410 - 3415
(2020/07/30)
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- Hypervalent Iodine Mediated Efficient Solvent-Free Regioselective Halogenation and Thiocyanation of Fused N -Heterocycles
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A facile, rapid, metal-free regioselective halogenation and thiocyanation of imidazo[1,2- a ]pyridine/pyrimidine heterocycles has been achieved under solvent-free reaction conditions. Halogenations and thiocyanation of the heterocycles could be accomplish
- Alla, Manjula,Indukuri, Divakar Reddy,Potuganti, Gal Reddy
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supporting information
p. 1573 - 1579
(2019/08/07)
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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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- BENZO-IMIDAZOINDOLIZINE DERIVATIVE, ORGANIC ELECTROLUMINESCENCE ELEMENT MATERIAL USING THE SAME, AND ORGANIC ELECTROLUMINESCENCE ELEMENT AND ELECTRONIC DEVICE USING THE SAME
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The present invention relates to benzo-imidazoindolizine derivatives, organic electroluminescence devices comprising said derivative, and the use of said derivative in organic electroluminescence devices.
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- Chemodivergent synthesis of: N -(pyridin-2-yl)amides and 3-bromoimidazo[1,2- a] pyridines from α-bromoketones and 2-aminopyridines
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N-(Pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines were synthesized respectively from α-bromoketones and 2-aminopyridine under different reaction conditions. N-(Pyridin-2-yl)amides were formed in toluene via C-C bond cleavage promoted by I2/s
- Liu, Yanpeng,Lu, Lixue,Zhou, Haipin,Xu, Feijie,Ma, Cong,Huang, Zhangjian,Xu, Jinyi,Xu, Shengtao
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p. 34671 - 34676
(2019/11/13)
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- Synergy of Anodic Oxidation and Cathodic Reduction Leads to Electrochemical C—H Halogenation
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We herein uncovered an electrochemical C—H halogenation protocol that synergistically combines anodic oxidation and cathodic reduction for C—X bond formation. The reaction was demonstrated under exogenous-oxidant-free conditions. Moreover, this is the first example of activating CBr4, CHBr3, and CCl3Br under electrochemical conditions.
- Zhou, Zhilin,Yuan, Yong,Cao, Yangmin,Qiao, Jin,Yao, Anjin,Zhao, Jing,Zuo, Wanqing,Chen, Wenjie,Lei, Aiwen
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supporting information
p. 611 - 615
(2019/05/10)
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- K2S2O8-Mediated halogenation of 2-arylimidazo[1,2-a]pyridines using sodium halides as the halogen sources
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A convenient halogenation of 2-arylimidazo[1,2-a]pyridines using sodium chloride/bromide/iodide as the halogen sources in the presence of K2S2O8 as an easy-to-handle oxidizing agent was developed. The present work offers a
- Katrun, Praewpan,Kuhakarn, Chutima
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supporting information
p. 989 - 993
(2019/03/11)
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- Transition-metal-free regioselective C-H halogenation of imidazo[1,2-: A] pyridines: Sodium chlorite/bromite as the halogen source
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A facile transition-metal-free regioselective halogenation of imidazo[1,2-a]pyridines using sodium chlorite/bromite as the halogen source is presented. The reaction has provided an efficient method for the formation of C-Cl or C-Br bonds to synthesize 3-c
- Li, Junxuan,Tang, Jiayi,Wu, Yuanheng,He, Qiuxing,Yu, Yue
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p. 5058 - 5062
(2018/04/27)
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- Regiocontrolled functionalization of 2,3-dihalogenoimidazo[1,2-a]pyridines by Suzuki-Miyaura and Sonogashira cross-coupling reactions
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An efficient method for regiocontrolled functionalization of 2,3-dihalogenoimidazo[1,2-a]pyridine was developed. This sequence allowed the selective introduction of aryl, heteroaryl, alkyl and alkynyl substituents at both 2- and 3-positions, by using Suzu
- Delaye,Pénichon,Allouchi,Enguehard-Gueiffier,Gueiffier
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p. 4199 - 4203
(2017/07/10)
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- Copper-Mediated Aerobic Oxidative Synthesis of 3-Bromo-imidazo[1,2-a]pyridines with Pyridines and Enamides
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A conversion of pyridines and enamides for the synthesis of 3-bromo-imidazo[1,2-a]pyridines was developed by copper-mediated aerobic oxidative coupling in a one-pot manner. This procedure tolerates various functional groups and affords a series of 3-bromo
- Zhou, Xiaoqiang,Yan, Hao,Ma, Chaowei,He, Yongqin,Li, Yamin,Cao, Jinhui,Yan, Rulong,Huang, Guosheng
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- An efficient access to 2,3-diarylimidazo[1,2-a]pyridines via imidazo[1,2-a]pyridin-2-yl triflate through a Suzuki cross-coupling reaction-direct arylation sequence
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An efficient method to prepare 2,3-diarylimidazo[1,2-a]pyridines is described. The procedure involves a Suzuki cross-coupling reaction followed by a direct arylation at position 3. Imidazo[1,2-a]pyridin-2-yl triflate was identified as a suitable coupling partner, permitting access to a variety of highly functionalized 2,3-diarylimidazo[1,2-a]pyridines.
- Marhadour, Sophie,Bazin, Marc-Antoine,Marchand, Pascal
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p. 297 - 300
(2012/01/31)
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- Influence of the 2-aryl group on the ipso electrophilic substitution process of 2-arylimidazo[1,2-a]pyridines
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A systematic study of electrophilic substitution reactions of 3-nitroso-2-arylimidazo[1,2-a]pyridine confirmed that the nitroso group may be ipso-substituted by bromine (NBS in DMF) and that bromine in turn may be substituted by the nitroso group. Electro
- Salgado-Zamora, Hector,Velazquez, Manuel,Mejia, Daniel,Campos-Aldrete,Jimenez, Rogelio,Cervantes, Humberto
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- REACTION OF DIHALOCARBENES WITH 2-(BENZYLIDENEAMINO)PYRIDINES. CYCLIZATION OF 2-(BENZYLIDENEAMINO)PYRIDINIUM DIHALOMETHYLIDS TO GIVE 2-ARYL-3-HALOIMIDAZOPYRIDINES
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Pyridinium dichloromethylids, formed in the reaction of dichlorocarbene with 2-(benzylideneamino)pyridines, undergo intramolecular 1,5-cyclization to give 2-aryl-8-chloroimidazopyridines, which undergo partial conversion to 2-aryl-3-chloro-4H-pyrid
- Khlebnikov, A. F.,Kostik, E. I.,Kostikov, R. R.
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p. 636 - 642
(2007/10/02)
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