- A multi pathway coupled domino strategy: I2/ TBHP-promoted synthesis of imidazopyridines and thiazoles via sp3, sp2 and sp C-H functionalization
-
I2/TBHP-promoted, one-pot, multi pathway synthesis of imidazopyridines and thiazoles has been achieved through readily available ethylarenes, ethylenearenes and ethynearenes. I2/TBHP as an initiator and oxidant is used to realize the C-H functionalization of this domino reaction. Simple and available starting materials, wide range of functional group tolerance, high potential for drug activity of the products and application in production are the advantageous features of this method.
- Feng, Lei,Li, Shichen,Ma, Chen,Wang, Xinfeng,Wang, Yishou,Yao, Yiming
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p. 5919 - 5927
(2022/03/31)
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- Oxidation Potential-Guided Electrochemical Radical-Radical Cross-Coupling Approaches to 3-Sulfonylated Imidazopyridines and Indolizines
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Oxidation potential-guided electrochemical radical-radical cross-coupling reactions between N-heteroarenes and sodium sulfinates have been established. Thus, simple cyclic voltammetry measurement of substrates predicts the likelihood of successful radical-radical coupling reactions, allowing the simple and direct synthetic access to 3-sulfonylated imidazopyridines and indolizines. The developed electrochemical radical-radical cross-coupling reactions to sulfonylated N-heteroarenes boast the green synthetic nature of the reactions that are oxidant- and metal-free.
- Kim, Wansoo,Kim, Hun Young,Oh, Kyungsoo
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p. 15973 - 15991
(2021/07/26)
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- Iodine-Mediated Sulfenylation of Imidazo[1,2- a ]pyridines with Ethyl Arylsulfinates
-
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)
-
- Design, synthesis and anticancer activity of sulfenylated imidazo-fused heterocycles
-
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)
-
- Solvent and catalyst-free synthesis of imidazo[1,2-a]pyridines by grindstone chemistry
-
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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- Micellar Catalysis: Visible-Light Mediated Imidazo[1,2-a]pyridine C—H Amination with N-Aminopyridinium Salt Accelerated by Surfactant in Water
-
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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- Synthetic method of imidazopyridine compounds
-
The invention provides a novel method for synthesizing imidazopyridine compounds. According to the invention, aminopyridine compounds and sulfur ylide are used as original reaction substrates, iron phthalocyanine (FeIIPc) is used as a catalyst, and a series of the imidazopyridine compounds are obtained under the condition that the advantages of mildness, greenness, high efficiency, wide substrateuniversality and the like are achieved.
- -
-
Paragraph 0054-0067
(2021/03/24)
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- A simple and efficient route to 2-arylimidazo[1,2-a]pyridines and zolimidine using automated grindstone chemistry
-
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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- Microwave-assisted synthesis and luminescent activity of imidazo[1,2-a]pyridine derivatives
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In this work, a series of phenacyl bromide derivatives was synthesized and employed as key intermediate for the synthesis of substituted imidazo[1,2-a]pyridines. First, phenacyl bromide molecules were obtained from the bromination reaction of acetophenones assisted by microwave irradiation, obtaining the products 4a-v in a 15 minutes reaction with yields in the range of 50% to 99%. Subsequently, the conjugation of these molecules with 2-aminopyridine conduced to the production of imidazo[1,2-a]pyridine derivatives (7a-v) in a 60-second reaction with yields of 24% to 99%. Improved yields were determined with respect to those obtained with more tedious methodologies like thermally and mechanically assisted routes. Intense luminescence emissions in the purple and blue regions of the electromagnetic spectra were observed under UV excitation according to the nature of the substituents. This environmentally friendly methodology is expected to constitute an important class of organic compounds for the development of biomarkers, photochemical sensors, and medicinal applications.
- Rodríguez, Juan C.,Maldonado, Rony A.,Ramírez-García, Gonzalo,Díaz Cervantes, Erik,de la Cruz, Fabiola N.
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supporting information
p. 2279 - 2287
(2020/03/16)
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- PhI(OAc)2-mediated oxidative C[sbnd]H sulfoximination of imidazopyridines under mild conditions
-
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
-
supporting information
(2019/11/26)
-
- Design, one-pot green synthesis and antimicrobial evaluation of novel imidazopyridine bearing pyran bis-heterocycles
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Herein, we report design, one pot synthesis and antibacterial evaluation of novel imidazopyridine bearing pyran bis-heterocycles. The compounds were synthesized in an aqueous solution of gluconic acid under both conventional heating and ultrasound irradiation. The target compounds were obtained in good to moderate yields with yield of 65–88% in 20–60 min under ultrasonic irradiation. The compounds were characterized by spectroscopic methods IR, 1H NMR, 13C NMR, MS and HRMS. X-ray single crystal structure of 7i was also determined. The compounds were evaluated for antibacterial activity by measuring zone of inhibition using disk diffusion method that revealed that some compounds were inhibiting the growth of Gram +ve and Gram -ve bacteria. Result of minimum inhibitory concentration (MIC) showed that 7a, 7h & 7k from a series 7a-7k inhibited the growth of S. aureus. The minimum bactericidal concentration (MBC) value was determined for 7a, 7h & 7k. MBC/MIC ratio of the derivatives 7a, 7k & 7h suggest former two derivatives act as bactericidal agent & later act as bacteriostatic agents against Gram +ve bacteria. Haemolysis results showed that compounds are non-cytotoxic to erythrocytes.
- Thakur, Ashima,Pereira, Gavin,Patel, Chetananda,Chauhan, Vinita,Dhaked, Ram Kumar,Sharma, Abha
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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
-
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
-
supporting information
p. 363 - 368
(2020/02/27)
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- CuCl2-catalyzed N[sbnd]O bond cleavage of oxime esters: Approach to imidazoheterocycles and furo[3,2-c]chromenyl fused imidazoles
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An articulate approach to a diverse set of imidazoheterocycles in good to high yields via a copper-catalyzed aza-annulation of several oxime esters with a group of 2-amino-azaarenes was developed. The above cyclization reaction probably proceeds via a single electron transfer process which embodies a new technique for creating two new C[sbnd]N bonds for imidazole ring synthesis. Gratifyingly, the implementation of this chemistry could be further stretched to the synthesis of a novel class of fused imidazoles bearing a furo[3,2-c]chromene moiety via a sequential C[sbnd]N bond formation, followed by C(sp2)-H functionalization/5-endo-dig-oxacyclization (C[sbnd]C and C[sbnd]O bonds) of in situ produced fused imidazoles with cyclic enynones in the presence of copper(II) as a π-electrophilic Lewis acid catalyst.
- Gudimella, Santosh K.,Kaur, Amanpreet,Kumar, Ram,Samanta, Sampak
-
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- Imidazopyridine compound, pharmaceutical composition containing the same, and preparation method and application thereof (by machine translation)
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Specifically discloses a pharmaceutical composition containing the compound and a pharmaceutically acceptable salt or a pharmaceutically acceptable solvate [1,2 - a] of the compound, and the preparation method, comprises the following steps of inhibiting, protein selectivity, drug effect strong STAT3 patent medicine, safety and the like, and the like . is particularly suitable for preventing and, or treating tumor growth and metastasis as well as pharmaceutical composition and pharmaceutical acceptable salt or pharmaceutically acceptable salt or pharmaceutically acceptable solvate of the compound in preparing STAT3 high-expression cell abnormal proliferation, form change and exercise function hyperthyroidism, and other related diseases / and are disclosed in the present invention. (by machine translation)
- -
-
Paragraph 0062-0066; 0255-0259
(2020/05/01)
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- Novel one step synthesis of imidazo[1,2-a]pyridines and Zolimidine via iron/iodine-catalyzed Ortoleva-King type protocol
-
Imidazo[1,2-a]pyridines form versatile scaffolds in pharmaceutical industry arising from their diverse biological activities. The synthesis of these molecules thus has been of great interest and resulted in the development of a large number of new methodologies. Herein we describe the first iron-catalyzed Ortoleva-King type protocol towards the synthesis of these fused heterocyclic compounds. This methodology employs cheap and easily available FeCl3·6H2O and molecular iodine as the catalytic system. The procedure has been well explored by extending the substrate scope with a variety of aromatic ketones and 2-aminopyridines to furnish different imidazo[1,2-a]pyridine derivatives in moderate to good yields. A successful application of this protocol was also demonstrated by achieving direct one step synthesis of the gastro protective drug, Zolimidine.
- Ujwaldev, Sankuviruthiyil Mohanan,Rohit,Harry, Nissy Ann,Anilkumar, Gopinathan
-
-
- Electrochemical oxidative selenylation of imidazo[1,2–a]pyridines with diselenides
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Electrochemical oxidative selenylation of imidazo[1,2–a]pyridines has been developed. The reaction proceeds in an undivided electrochemical cell equipped with glassy carbon electrodes employing LiClO4 as a supporting electrolyte. This approach
- Kim, Yeon Joo,Kim, Dae Young
-
supporting information
p. 739 - 742
(2019/02/09)
-
- Ultrasound-assisted synthesis of imidazo[1,2-a]pyridines an d sequential one-pot preparation of 3-selanyl-imidazo[1,2-a]pyridine derivatives
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A simple and rapid method to synthesize imidazo[1,2-a]pyridines starting from 2-aminopyridine and 2-bromoacetophenone derivatives under ultrasonic irradiation was developed. This protocol tolerates a wide range of 2-bromoacetophenone derivatives to produce a variety of imidazo[1,2-a]pyridines in good to excellent yields. Additionally, the one-pot preparation of 3-(organylselanyl)imidazo[1,2-a]pyridines via a sequential method is presented. In this case, different diorganyl diselenides were used as starting materials to afford the corresponding coupling products in excellent yields and short reaction times under sonication. The reactions were conducted in PEG-400, a cheap and nontoxic solvent, compatible with the ultrasound conditions in an environmentally benign process.
- Vieira, Beatriz M.,Padilha, Nathalia,Nascimento, Nelson M.,Perin, Gelson,Alves, Diego,Schumacher, Ricardo F.,Lenard?o, Eder J.
-
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- Rhodium(II)-Catalyzed Regioselective C3-Alkylation of 2-Arylimidazo[1,2-a]pyridines with Aryl Diazoesters
-
A regioselective C3-alkylation based on the reaction of 2-arylimidazo[1,2-a]pyridines with a wide range of aryl α-diazoesters in the presence of a Rh(II) catalyst in dichloroethane at room temperature was developed. This method could be applied in the synthesis of benzoimidazoquinolizinone and cycloheptaimidazopyridinone, which are novel heterocyclic scaffolds. (Figure presented.).
- Kim, Hyunseok,Byeon, Minhyeon,Jeong, Eunchong,Baek, Yonghyeon,Jeong, Seung Jin,Um, Kyusik,Han, Sang Hoon,Han, Gi Uk,Ko, Gi Hoon,Maeng, Chanyoung,Son, Jeong-Yu,Kim, Dongwook,Kim, Sung Hong,Lee, Kooyeon,Lee, Phil Ho
-
supporting information
p. 2094 - 2106
(2019/03/21)
-
- Electrochemical Oxidative C—H Sulfenylation of Imidazopyridines with Hydrogen Evolution
-
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
-
supporting information
p. 49 - 52
(2019/01/04)
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- Use of imidazo[1,2-a]pyridine as a carbonyl surrogate in a mannich-like, catalyst free, one-pot reaction
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Derivatization of imidazo[1,2-a]pyridine scaffolds have gained considerable attention due to the biological significance of therapeutics based on the imidazopyridine core. By utilizing a catalyst-free, “Mannich type” reaction, we developed a simple and efficient protocol to aminomethylate the C-3 position of imidazo[1,2-a]pyridine through a multicomponent, de-carboxylation reaction involving imidazo[1,2-a]pyridine, a secondary amine, and glyoxylic acid. The developed protocol re-quires mild reaction conditions and furnishes diverse imid-azo[1,2-a]pyridine analogues from commercially available starting materials. Additionally, the current protocol improves prior methods, which were limited by the amine substrate scope. Taken together, this current methodology permits rapid diversification of imidazo[1,2-a]pyridines to enhance combinatorial efficiency in the drug discovery processes.
- Naresh, Gunaganti,Lakkaniga, Naga Rajiv,Kharbanda, Anupreet,Yan, Wei,Frett, Brendan,Li, Hong-Yu
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p. 770 - 777
(2019/01/14)
-
- Transition-Metal-Free Direct Trifluoromethylation and Perfluoroalkylation of Imidazopyridines under Mild Conditions
-
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
-
supporting information
p. 1559 - 1563
(2019/02/19)
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- Electrochemical oxidative C-H/N-H cross-coupling for C-N bond formation with hydrogen evolution
-
Under metal catalyst-free and exogenous-oxidant-free conditions, a series of C-3 aminated imidazo[1,2-a]pyridines were synthesized by electrochemical intermolecular oxidative C-H/N-H cross-coupling. Furthermore, by using a catalytic amount of ferrocene as
- Yu, Yi,Yuan, Yong,Liu, Huilin,He, Min,Yang, Mingzhu,Liu, Pan,Yu, Banying,Dong, Xuanchi,Lei, Aiwen
-
supporting information
p. 1809 - 1812
(2019/02/12)
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- Exogenous-oxidant-free electrochemical oxidative C-H phosphonylation with hydrogen evolution
-
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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- Metal-Free Site-Specific Hydroxyalkylation of Imidazo[1,2- A[pyridines with Alcohols through Radical Reaction
-
An effective approach to realize the direct hydroxyalkylation of imidazo[1,2-a]pyridines with alcohols promoted by di-tert-butyl peroxide was described without any metal catalyst. It is the first time that the dehydrogenative C(sp3)-C(sp2) coupling of imidazo[1,2-a]pyridines with alcohols occurred regioselectively at the C-5 position of imidazo[1,2-a]pyridines. Multisubstituted imidazopyridine derivatives were smoothly synthesized in moderate to good yields. Through a series of control experiments, a free-radical pathway was proposed to explain the experiment.
- Jin, Shengzhou,Xie, Bo,Lin, Sen,Min, Cong,Deng, Ruihong,Yan, Zhaohua
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supporting information
(2019/05/07)
-
- Metal-Free Site-Specific Hydroxyalkylation of Imidazo[1,2- a]pyridines with Alcohols through Radical Reaction
-
An effective approach to realize the direct hydroxyalkylation of imidazo[1,2-a]pyridines with alcohols promoted by di-tert-butyl peroxide was described without any metal catalyst. It is the first time that the dehydrogenative C(sp3)-C(sp2) coupling of imidazo[1,2-a]pyridines with alcohols occurred regioselectively at the C-5 position of imidazo[1,2-a]pyridines. Multisubstituted imidazopyridine derivatives were smoothly synthesized in moderate to good yields. Through a series of control experiments, a free-radical pathway was proposed to explain the experiment.
- Jin, Shengzhou,Xie, Bo,Lin, Sen,Min, Cong,Deng, Ruihong,Yan, Zhaohua
-
supporting information
p. 3436 - 3440
(2019/05/10)
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- Rapid Construction of Fused Heteropolycyclic Aromatics via Palladium-Catalyzed Domino Arylations of Imidazopyridine Derivatives
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By using diaryliodonium salts, a novel approach of a palladium-catalyzed cascade of diarylation/intramolecular dehydrogenative coupling reaction has been developed in the synthesis of phenanthro-imidazopyridine fused heteropolycycles. The method can toler
- Xue, Chenwei,Han, Jianwei,Zhao, Min,Wang, Limin
-
supporting information
p. 4402 - 4406
(2019/05/08)
-
- Iodide-Catalyzed Phosphorothiolation of Heteroarenes Using P(O)H Compounds and Elemental Sulfur
-
Organothiophosphates have found widespread application as biologically active compounds and synthetic intermediates in medicinal chemistry. The first transition-metal-free one-pot direct synthesis of heterocyclic phosphorothioates involving indole or imidazo[1,2-a]pyridine derivatives, elemental sulfur, and P(O)H compounds is presented. The use of NaI or KI as a catalyst, tert-butyl hydroperoxide as an oxidant, various indole and imidazo[1,2-a]pyridine derivatives are tolerant in this transformation, affording the corresponding products in good to excellent yields. Moreover, this method can be easily adapted to large-scale preparation. O,O-Diethyl S-(1-phenyl-1H-indol-3-yl) phosphorothioate presents potent anti-inflammatory activity in lipopolysaccharide (LPS)-stimulated RAW264.7 cells in a dose-dependent manner. (Figure presented.).
- Shi, Shanshan,Chen, Jun,Zhuo, Shaohua,Wu, Zi'ang,Fang, Meijuan,Tang, Guo,Zhao, Yufen
-
supporting information
p. 3210 - 3216
(2019/05/16)
-
- Formation of Methylene Linkage for N-Heterocycles: Sequential C-H and C-O Bond Functionalization of Methanol with Cosolvent Water
-
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
-
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
- -
-
Paragraph 0352-0355
(2019/03/08)
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- One-pot NBS-promoted synthesis of imidazoles and thiazoles from ethylarenes in water
-
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
-
-
- Iodine mediated oxidative cross coupling of 2-aminopyridine and aromatic terminal alkyne: A practical route to imidazo[1,2-: A] pyridine derivatives
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A novel, transition-metal free route leading to imidazo[1,2-a]pyridine derivatives via iodine mediated oxidative coupling between 2-aminopyridine and aromatic terminal alkyne has been demonstrated. This newly developed method discloses an operationally simple way for the construction of imidazoheterocycles. Commercially available antiulcer drug zolimidine may readily be synthesized employing this method.
- Samanta, Surya Kanta,Bera, Mrinal K.
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p. 6441 - 6449
(2019/07/10)
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- Green procedure for highly efficient, rapid synthesis of imidazo[1,2-a]pyridine and its late stage functionalization
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We unfold a rapid synthetic protocol for the preparation of imidazo[1,2-a]pyridine in cyclohexane. This methodology includes several advantages like shorter reaction time, catalyst free, broader substrate scope, and good yields of the desired products. La
- Ghosh, Prasanjit,Ganguly, Bhaskar,Kar, Barnali,Dwivedi, Seema,Das, Sajal
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p. 1076 - 1084
(2018/04/02)
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- Method for synthesizing novel imidazole pyranone compounds containing chalcogens
-
The invention discloses a method for synthesizing novel imidazole pyranone compounds containing chalcogens. The method comprises the steps as follows: firstly, 4-hydroxycoumarin compounds and triflicanhydride react, and 4-triflate-based coumarins are gene
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-
Paragraph 0045; 0047
(2018/04/02)
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- Synthetic method of novel 3-(benzothiazolyl)imidazo[1,2-a]pyridine bis-heterocycle compound
-
The invention relates to the field of pharmaceutical chemistry, in particular to a synthetic method of a novel 3-(benzothiazolyl)imidazo[1,2-a]pyridine bis-heterocycle compound, as well as applicationin inhibiting the proliferation of cancer cells. The sy
- -
-
Paragraph 0025
(2018/11/03)
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- Efficient Access to Imidazo[1,2- a] pyridines/pyrazines/pyrimidines via Catalyst-Free Annulation Reaction under Microwave Irradiation in Green Solvent
-
An expeditious catalyst-free heteroannulation reaction for imidazo[1,2-a]pyridines/pyrimidines/pyrazines was developed in green solvent under microwave irradiation. Using H2O-IPA as the reaction medium, various substituted 2-aminopyridines/pyra
- Rao, R. Nishanth,Mm, Balamurali,Maiti, Barnali,Thakuria, Ranjit,Chanda, Kaushik
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supporting information
p. 164 - 171
(2018/03/21)
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- Natural products as sources of new fungicides (V): Design and synthesis of acetophenone derivatives against phytopathogenic fungi in vitro and in vivo
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A series of acetophenone derivatives (10a–10i, 11, 12a–12g, 13a–13g, 14a–14d and 15a–15l) were designed, synthesized and evaluated for antifungal activities in vitro and in vivo. The antifungal activities of 53 compounds were tested against several plant pathogens, and their structure–activity relationship was summarized. Compounds 10a–10f displayed better antifungal effects than two reference fungicides. Interestingly, the most potent compound 10d exhibited antifungal properties against Cytospora sp., Botrytis cinerea, Magnaporthe grisea, with IC50 values of 6.0–22.6 μg/mL, especially Cytospora sp. (IC50 = 6.0 μg/mL). In the in vivo antifungal assays, 10d displayed the significant protective efficacy of 55.3% to Botrytis cinerea and 73.1% to Cytospora sp. The findings indicated that 10d may act as a potential pesticide lead compound that merits further investigation.
- Dan, Wen-Jia,Tuong, Thi-Mai-Luong,Wang, Da-Cheng,Li, Ding,Zhang, An-Ling,Gao, Jin-Ming
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supporting information
p. 2861 - 2864
(2018/07/25)
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- Catalyst free, C-3 functionalization of imidazo[1,2-a]pyridines to rapidly access new chemical space for drug discovery efforts
-
Multicomponent reactions (MCRs) are robust tools for the rapid synthesis of complex, small molecule libraries for use in drug discovery and development. By utilizing MCR chemistry, we developed a protocol to functionalize the C-3 position of imidazo[1,2-a
- Gunaganti, Naresh,Kharbanda, Anupreet,Lakkaniga, Naga Rajiv,Zhang, Lingtian,Cooper, Rose,Li, Hong-yu,Frett, Brendan
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supporting information
p. 12954 - 12957
(2018/11/23)
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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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- Method for synthesizing 2-arylimidazo[1, 2-a]pyridine compounds from ethylbenzene compounds
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The invention discloses a method for synthesizing 2-arylimidazo[1, 2-a]pyridine compounds from ethylbenzene compounds and belongs to the field of 2-arylimidazo[1, 2-a]pyridine derivative synthesis. The method comprises that an ethylbenzene compound, a phase transfer catalyst, N-bromosuccinimide NBS and AIBN are added into water, the solution undergoes a reaction at 60 DEG C, an inorganic base andan alpha-aminopyridine compound are added into the reaction product, and the mixture undergoes a reaction at 80 DEG C to produce the 2-arylimidazo[1, 2-a]pyridine compound. The method creatively utilizes the ethylbenzene compound to synthesize the 2-arylimidazo[1, 2-a]pyridine compound. Compared with the 2-bromoacetophenone commonly used as a 2-arylimidazo[1, 2-a]pyridine compound synthesis raw material in the industry, the ethylbenzene compound is cheaper and more easily available.
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Paragraph 0060; 0061; 0062; 0063
(2018/11/27)
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- Method for synthesizing 2-arylimidazo[1, 2-a]pyridine compound
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The invention discloses a method for synthesizing a 2-arylimidazo[1, 2-a]pyridine compound and belongs to the technical field of organic synthesis. The method comprises that an ethylbenzene compound,dibromohydantoin DBH and t-butyl hydroperoxide TBHP are added into water and undergo a reaction at 60 DEG C, an inorganic base and an alpha-aminopyridine compound are added into the reaction product and the mixture undergoes a reaction at 80 DEG C to produce a desired product 2-arylimidazo[1, 2-a]pyridine compound. The 2-arylimidazo[1, 2-a]pyridine compound is synthesized from the ethylbenzene compound which is cheaper and more readily available than the 2-arylimidazo[1, 2-a]pyridine compounds such as 2-bromoacetophenone commonly used in the industry.
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Paragraph 0058; 0059; 0060; 0061
(2018/11/27)
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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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- Iron-Catalyzed Dehydrogenative sp3-sp2 Coupling via Direct Oxidative C-H Activation of Acetonitrile
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An iron-catalyzed dehydrogenative sp3-sp2 coupling of acetonitrile and 2-arylimidazo[1,2-a]pyridine has been realized, which can serve as a novel approach toward heteroarylacetonitriles. The merit of this strategy is illustrated by the breadth of functional groups tolerated in the transformation and the fast access to pharmaceuticals (such as zolpidem) directly from the heteroarylacetonitriles.
- Su, Huimin,Wang, Luyao,Rao, Honghua,Xu, Hao
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supporting information
p. 2226 - 2229
(2017/05/12)
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- NBS mediated protocol for the synthesis of N-bridged fused heterocycles in water
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A facile and environmental friendly protocol for the synthesis of N-bridged fused bicyclic compounds such as imidazo[1,2-a]pyridines, imidazo[1,2-a]pyrimidines, and imidazo[2,1-b]thiazole, from commercially available starting materials has been developed.
- Bhagat, Saket B.,Telvekar, Vikas N.
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supporting information
p. 3662 - 3666
(2017/08/23)
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- Rapid and efficient one-pot microwave-assisted synthesis of 2-phenylimidazo[1,2-a]pyridines and 2-phenylimidazo[1,2-a]quinoline in water–PEG-400
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An effective, expeditious, environmentally benign one-pot synthesis of 2-phenylimidazo[1,2-a]pyridines and 2-phenylimidazo[1,2-a]quinoline from easily available starting materials as aromatic carbonyl compound, 2-amino pyridine, succinamide, and in situ g
- Jadhav, Santosh A.,Shioorkar, Mahesh G.,Chavan, Omprakash S.,Sarkate, Aniket P.,Shinde, Devanand B.
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p. 285 - 290
(2017/02/10)
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- Syntheses of biodynamic heterocycles: baker’s yeast-assisted cyclocondensations of organic nucleophiles and phenacyl chlorides
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Substituted phenacyl chlorides (1a–f) were cyclocondensed with nucleophiles thiourea (2a) and thiobenzamide (2b) in presence of baker’s yeast (Saccharomyces cerevisiae) as whole-cell enzyme source in acetonitrile at room temperature to obtain 4-(4-substituted phenyl)thiazol-2-amines (3a–f) and 4-(substituted phenyl)-2-phenylthiazoles (4a–f), respectively. Moreover, substituted phenacyl chlorides also reacted with nucleophiles 2-amino-1,3,4-thiadiazole (2c), o-phenylenediamine (2d), 1-amino-2-mercapto-5-phenyl triazole (2e), and pyridin-2-amine (2f) at room temperature in presence of baker’s yeast to give fused heterocycles 6-(4-substituted phenyl)-2-phenylimidazo[2,1-b][1,3,4]thiadiazoles (5a–f), 2-(4-substituted phenyl)quinoxalines (6a–f), 6-(4-substituted phenyl)-3-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines (7a–f), and 2-(4-substituted phenyl)H-imidazo[1,2-a]pyridines (8a–f), respectively. The experimental conditions for these cyclocondensations were optimized to obtain the biodynamic heterocycles in high yield. The unique features of this work are use of baker’s yeast as a cheap and readily available natural source of biocatalyst, noticeable rate acceleration, convenient route to products, cost effectiveness, and scalability.
- Khillare, Lalit D.,Pratap, Umesh R.,Bhosle, Manisha R.,Dhumal, Sambhaji T.,Bhalerao, Mahendra B.,Mane, Ramrao A.
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p. 4327 - 4337
(2017/07/22)
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- Au-catalyzed domino process synthesis of imidazo[1,2-a]pyridines from 2-aminopyridine and N-tosylhydrazones: An efficient C[sbnd]N bond formation reaction
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A novel Au-catalyzed domino reaction for the synthesis of imidazo[1,2-a]pyridines from 2-aminopyridine and N-tosylhydrazones has been developed using molecular oxygen. It represents a new strategy for the formation of C[sbnd]N bonds. This transformation demonstrated a broad tolerance toward the substrates and allowed the generation of a diverse imidazo[1,2-a]pyridine derivatives with good yields.
- Guo, Pengfeng,Huang, Shuyu,Mo, Jiaxian,Chen, Xiaoyan,Jiang, Hangqi,Chen, Weifeng,Cai, Hehuan,Zhan, Haiying
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- Iodine–ammonium acetate promoted reaction between 2-aminopyridine and aryl methyl ketones: a novel approach towards the synthesis of 2-arylimidazo[1,2-a]pyridines
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I2–NH4OAc was found to be an efficient system for the metal-free synthesis of diversely substituted imidazo[1,2-a]pyridines 3a–r from 2-aminopyridine 1 and aryl methyl ketones 2a–r in one pot. 2-Arylimidazo[1,2-a]pyridines 3a–r were
- Kour, Dilpreet,Khajuria, Rajni,Kapoor, Kamal K.
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supporting information
p. 4464 - 4467
(2016/09/14)
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- Synthesis and antimicrobial activity of novel imidazo[1,2-a]pyridinopyrimidine-2,4,6(1H,3H,5H)-triones and thioxopyrimidine-4,6(1H,5H)diones
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A novel series of imidazo[1,2-a]pyridinopyrimidine-2,4,6(1H,3H,5H)-triones and thioxopyrimidine-4,6(1H,5H)diones were synthesized via multistep synthesis starting from 2-aminopyridine on cyclisation with phenacyl bromide followed by Vilsmeier-Haack and Kn
- Rajitha,Ravibabu,Ramesh,Rajitha
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p. 1989 - 1998
(2016/03/16)
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- One pot synthesis of substituted imidazopyridines and thiazoles from styrenes in water assisted by NBS
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Heating of commercially available styrenes with NBS in water followed by reaction with 2-aminopyridines or thioamides afforded important heterocyclic scaffolds in a one pot procedure. The reaction proceeds via co-oxidant free, 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 imidazopyridines and thiazoles.
- Shinde, Mahesh H.,Kshirsagar, Umesh A.
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supporting information
p. 1455 - 1458
(2016/04/04)
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