- Facile access to novel 3-acylimidazo[1,2-a]pyrimidines under microwave irradiation
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Treatment of mono-, bis- and tris(ω-bromoacetophenone) derivatives with N,N-dimethylformamidine derivative of 2-aminopyrimidine, afforded the novel 3-aroyl or heteroyl derivatives of imidazo[1,2-α]pyrimidine, bis(imidazo[1,2-α]pyrimidine) and tris(imidazo
- Shaaban, Mohamed R.
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- Tandem [8 + 2] cycloaddition-[2 + 6 + 2] dehydrogenation reactions involving imidazo[1,2- a ]pyridines and imidazo[1,2- a ]pyrimidines
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The reaction between benzynes and imidazo[1,2-a]pyridines (pyrimidines) to form benzo[a]imidazo[5,1,2-cd]indolizines and 2,3,9c-triazocyclopenta[j,k] fluorenes has been studied computationally and experimentally. It is found that these reactions take plac
- Aginagalde, Maialen,Vara, Yosu,Arrieta, Ana,Zangi, Ronen,Cebolla, Vicente L.,Delgado-Camon, Arantzazu,Cossio, Fernando P.
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- Hypervalent Iodine in Synthesis 93. A Facile Synthesis of 2-Substituted Imidazo[1,2-a]pyrimidines by Cyclocondensation of Alkynyl(phenyl)iodonium Salts and 2-Aminopyrimidine
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Simple stirring of a mixture of the alkynyl(phenyl)iodonium salts 1 with 2-aminopyrimidine 2 in chloroform under reflux for two hours in the presence of K2CO3 gave, after workup, the 2-substituted imidazo[1,2-a]pyrimidines 3 in moderate to good yields. A possible mechanism for the formation of 3 involves the intramolecular cyclization of the intermediate alkylidenecarbene 6.
- Liu, Zhi,Chen, Zhen-Chu,Zheng, Qin-Guo
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- Metal complex and application thereof
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The invention relates to a metal complex and application thereof, the metal complex is a metal complex electrophosphorescent luminescent material with a pyrimidine fused ring structure, and is a series of metal complexes obtained by taking modified pyrimi
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Paragraph 0159-0163
(2021/08/06)
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- Synthesis and anti-inflammatory activity of 1,2-3-substituted 2a1,4,5-triazacyclopenta[cd]indene derivatives
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The present study reports the synthesis of 1,2-3-substituted-2a1,4,5-triazacyclopenta[cd]indene derivatives. The synthetic methodology includes some of the prominent reaction steps as specified in sequence (i) Bromination of acetophenones (ii) Condensation of 2-bromo-1-(substituted phenyl) ethanone derivatives with 2-aminopyrimidine, and (iii) Coupling of imidazo[1,2-a]pyrimidine derivatives with 1,2-diaryl/diaklylethynes. The structures of the newly synthesized derivatives have been determined by 1H NMR, 13C NMR, LC-MS, and IR spectral analysis. Furthermore, these derivatives were screened for their preliminary anti-inflammatory activities using Carrageenan induced paw edema test method. These promising screening results suggested a huge potential for the molecular diversity from present compounds that can be inflated to better lead candidates.
- Sanivarapu, Sumalatha,Vaddiraju, Namratha,Velide, Lakshmi
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p. 1461 - 1470
(2019/07/05)
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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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- 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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- 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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- Novel Combretastatin-2-aminoimidazole Analogues as Potent Tubulin Assembly Inhibitors: Exploration of Unique Pharmacophoric Impact of Bridging Skeleton and Aryl Moiety
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Combretastatin A-4 (CA-4) in phosphate and serine pro-drug forms is under phase II clinical trials. With our interest of discovering CA-4 inspired new chemical entities, a novel series of 4,5-diaryl-2-aminoimidazole analogues of the compound was designed
- Chaudhary, Vikas,Venghateri, Jubina B.,Dhaked, Hemendra P. S.,Bhoyar, Anil S.,Guchhait, Sankar K.,Panda, Dulal
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p. 3439 - 3451
(2016/05/19)
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- Highly Efficient and Practical Thiocyanation of Imidazopyridines Using an N-Chlorosuccinimide/NaSCN Combination
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A direct C–H thiocyanation of imidazo[1,2-a]pyridines, and a practical sequential one-pot condensation/C–H thiocyanation process, using a combination of N-chlorosuccinimide/NaSCN for the synthesis of 3-thiocyanatoimidazo[1,2-a]pyridines have been develope
- Zhang, Hailei,Wei, Qian,Wei, Shiqiang,Qu, Jingping,Wang, Baomin
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p. 3373 - 3379
(2016/07/23)
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- Ligand-Controlled Synthesis of Azoles via Ir-Catalyzed Reactions of Sulfoxonium Ylides with 2-Amino Heterocycles
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An iridium-catalyzed method was developed for the synthesis of imidazo-fused pyrrolopyrazines. The presence or absence of a nitrogenated ligand controlled the outcome of the reaction, leading to simple β-keto amine products in the absence of added ligand and the cyclized 7- and 8-substituted-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine products in the presence of ligand. This catalyst control was conserved across a variety of ylide and amine coupling partners. The substrate was shown to act as a ligand for the iridium catalyst in the absence of other ligands via NMR spectroscopy. Kinetic studies indicated that formation of the Ir-carbene was reversible and the slow step of the reaction. These mechanistic investigations suggest that the β-keto amine products form via an intramolecular carbene N-H insertion, and the imidazopyrrolopyrazines form via an intermolecular carbene N-H insertion.
- Phelps, Alicia M.,Chan, Vincent S.,Napolitano, José G.,Krabbe, Scott W.,Schomaker, Jennifer M.,Shekhar, Shashank
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p. 4158 - 4169
(2016/06/09)
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- Design, synthesis and biological evaluation of imidazopyridine/imidazopyrimidine-benzimidazole conjugates as potential anticancer agents
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A series of imidazopyridine/imidazopyrimidine-benzimidazole conjugates (11a-t) were synthesized and evaluated for their antiproliferative activity. All of these conjugates showed moderate to improved cytotoxic activity against the human cervical (Hela), l
- Kamal, Ahmed,Bharath Kumar,Lakshma Nayak,Reddy, Vangala Santhosh,Shaik, Anver Basha,Rajender,Kashi Reddy
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supporting information
p. 606 - 612
(2015/04/27)
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- General Method for the Preparation of Electron-Deficient Imidazo[1,2-a]pyridines and Related Heterocycles
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A new annulation method for the preparation of the imidazo[1,2-a]pyridine ring system under mild conditions is presented. Treatment of a 2-aminopyridine with a dimethylketal tosylate in acetonitrile at elevated temperature (80-140°C) in the presence of catalytic Sc(OTf)3 provides the imidazo[1,2-a]pyridine product in good yield. The annulation method is broadly applicable to electron-poor 2-aminopyridines and displays a complementary profile to the classic preparation of the imidazo[1,2-a]pyridine ring system by reaction of a bromoketone with electron-rich and -neutral substrates. The scope of the process and mechanistic considerations are discussed.
- McDonald, Ivar M.,Peese, Kevin M.
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supporting information
p. 6002 - 6005
(2016/01/09)
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- Direct one-pot synthesis of zolimidine pharmaceutical drug and imidazo[1,2-a]pyridine derivatives via I2/CuO-promoted tandem strategy
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An efficient one-pot synthetic protocol was developed for the synthesis of imidazo[1,2-a]pyridines from easily available starting materials: Aromatic ketones, α,β-unsaturated ketones, β-keto esters and 2-aminopyridines. The present reaction proceeded well in MeOH under the media of I2/CuO. By using this method, the marketed drug zolimidine could be prepared easily with 95% yield. All these target products were characterized by NMR, HRMS and IR spectra. Furthermore, the target compound 3fa was determined by X-ray crystallographic analysis.
- Cai, Qun,Liu, Mei-Cai,Mao, Bi-Ming,Xie, Xuan,Jia, Feng-Cheng,Zhu, Yan-Ping,Wu, An-Xin
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p. 881 - 884
(2015/03/04)
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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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- Structure-activity relationship of 4(5)-aryl-2-amino-1 H -imidazoles, N 1-substituted 2-aminoimidazoles and imidazo[1,2- a ]pyrimidinium salts as inhibitors of biofilm formation by salmonella typhimurium and pseudomonas aeruginosa
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A library of 112 4(5)-aryl-2-amino-1H-imidazoles, 4,5-diphenyl-2-amino-1H- imidazoles, and N1-substituted 4(5)-phenyl-2-aminoimidazoles was synthesized and tested for the antagonistic effect against biofilm formation by Salmonella Typhimurium and Pseudomo
- Steenackers, Hans P. L.,Ermolatev, Denis S.,Savaliya, Bharat,De Weerdt, Ami,De Coster, David,Shah, Anamik,Van Der Eycken, Erik V.,De Vos, Dirk E.,Vanderleyden, Jozef,De Keersmaecker, Sigrid C. J.
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scheme or table
p. 472 - 484
(2011/04/15)
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- Hypervalent iodine(III) sulfonate mediated synthesis of 2-arylimidazo[1,2-a]pyrimidines in liquid PEG-400
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PEG-400[poly(ethylene glycol-400)] is used as a "green" recyclable solvent in the one-pot synthesis of 2-arylimidazo[1,2-a]pyrimidines by reaction with ketones, [hydroxyl(2,4-dinitrobenzenesulfonyloxy)-iodo]benzene (HDNIB), and 2-aminopyrimidine. Signific
- Cheng, Hui-Ting,Hou, Rei-Sheu,Wang, Huey-Min,Kang, Iou-Jiun,Lin, Pei-Ying,Chena, Ling-Ching
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experimental part
p. 632 - 635
(2010/06/13)
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- A facile [hydroxy(tosyloxy)iodo]benzene mediated synthesis of 2-arylimidazo[1,2-a]pyrimidines and their conversion into 3-bromo-2- arylimidazo[1,2-a]pyrimidines
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α-Tosyloxyketone 2, obtained through hypervalent iodine oxidation of enolizable ketones using [hydroxy(tosyloxy)iodo]benzene (HTIB) in acetonitrile, on treatment with 2-aminopyrimidine 3 generates regioselectively 2-arylimidazo[1,2-a]pyrimidine 6 which up
- Aggarwal, Ranjana,Sumran, Garima
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p. 2690 - 2695
(2007/10/03)
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- Organic reactions in ionic liquids: Ionic liquid-accelerated one-pot synthesis of 2-arylimidazo[1,2-a]pyrimidines
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The room-temperature ionic liquid n-butylpyridinium tetrafluoroborate (BPyBF4) is used as a recyclable alternative to classical molecular solvents in the one-pot synthesis of 2-arylimidazo[1,2-a]pyrimidines by reaction with ketones, [hydroxy(tosyloxy)iodo]benzene, and 2-aminopyrimidine. Significant rate enhancements and improved yields have been observed. Copyright Taylor & Francis, Inc.
- Xie, Yuan-Yuan
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p. 1741 - 1746
(2007/10/03)
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- Synthesis of bridgehead nitrogen heterocycles on a solid surface
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Bridgehead nitrogen heterocycles were synthesized from heteroaromatic amidines and cyclic or acyclic α-bromoketones under solvent-free conditions at room temperature on a solid surface in excellent yields, which are higher than those obtained with hithert
- Ponnala, Shashikanth,Kumar, S. T. V. S. Kiran,Bhat, Bashir A.,Sahu, Devi Prasad
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p. 901 - 906
(2007/10/03)
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- Synthesis of 2-arylimidazo[1,2-a]pyrimidines by the Chichibabin synthesis in ionic liquids
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A series of 2-arylimidazo[1,2-a]pyrimidines has been synthesised in excellent yields by the Chichibabin synthesis in room temperature ionic liquids.
- Xu, Danqian,Liu, Baoyou,Zheng, Mei
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p. 645 - 647
(2007/10/03)
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- Synthesis and antibacterial activity of some imidazo[1,2-a[pyrimidine derivatives
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A series of 75 imidazo[1,2-a]pyrimidine derivatives were synthesized. The 'in vitro' antibacterial activity of these compounds and their corresponding α-bromoketones against a variety of gram (+), gram (-) bacteria and Mycobacterium species is reported. Some of the prepared derivatives exhibited potent antimicrobial activity.
- Rival,Grassy,Michel
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p. 1170 - 1176
(2007/10/02)
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- Antifungal activity in vitro of some imidazopyrimidine derivatives
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In regard to fungicidal activity of imidazole ring found in chemical compounds such as econazole, a series of 42 diversely substituted imidazopyrimidines was synthetized and examined for its antifungal activity in several species.
- Rival, Y,Grassy, G,Taudou, A,Ecalle, R
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- Acid azo dyes containing heterocyclic couplers
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Disclosed are novel acid azo dyes containing a sulfonated, sulfated or thiosulfated organothiothiadiazole azo moiety and a heterocyclic coupler which may be substituted. The dyes produce reddish-yellow to orange shades on, for example, hydrophobic textile
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- Indoline coupled isothiazole azo dyes
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Disclosed are novel azo dyes containing an isothiazole azo moiety which may be substituted, and a heterocyclic coupler which also may be substituted. The dyes produce yellow shades on, for example, hydrophobic textile fiber including polyesters, polyamide
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- Imidazoindole derivatives and pharmaceutical compositions comprising imidazoindole derivatives
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Pharmaceutical composition for chelating excess iron in a mammal and facilitating the removal of excess iron from the mammalian body are disclosed which comprise as active ingredient an iron-chelating agent selected from the group consisting of 5H-pyrimid
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