- Pyridine Skeleton Synthesis Using Acetonitrile as C4N1 Units and Solvent
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The first [3 + 2 + 1] methodology for pyridine skeleton synthesis via cascade carbopalladation/cyclization of acetonitrile, arylboronic acids, and aldehydes was developed. This reaction proceeds via six step tandem reaction sequences involving the carbopalladation reaction of acetonitrile, a nucleophilic addition, a condensation, an intramolecular Michael addition, cyclization, and aromatization. Delightfully, both palladium acetate and supported palladium nanoparticles catalyzed this reaction with similar catalytic performance. The characterization results of the fresh and used supported palladium nanoparticle catalysts indicated that the reaction might be performed via a Pd(0)/Pd(II) catalytic cycle that began with Pd(0). Furthermore, the products showed good fluorescence characteristics. The green homogeneous/heterogenous catalytic methodologies pave a new way for constructing the pyridine skeleton.
- Bai, Chaolumen,Guo, Huifang,Liu, Xin,Liu, Dan,Sun, Zhaorigetu,Bao, Agula,Baiyin, Menghe,Muschin, Tegshi,Bao, Yong-Sheng
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p. 12664 - 12675
(2021/09/18)
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- Copper-catalyzed efficient access to 2,4,6-triphenyl pyridinesviaoxidative decarboxylative coupling of aryl acetic acids with oxime acetates
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An efficient and concise approach for the synthesis of 2,4,6-triphenyl pyridines has been developed through copper-catalysed oxidative decarboxylative coupling of C(sp3) aryl acetic acids with oxime acetates in DMF at 150 °C under an oxygen atm
- Bharat Kumar, Karasala,Chinnari, Lekkala,Shyamala, Pulipaka,Siddaiah, Vidavalur,Varaprasad, Bodala
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supporting information
p. 15205 - 15209
(2021/09/06)
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- Convenient one-pot synthesis of 1,2,4-oxadiazoles and 2,4,6-triarylpyridines using graphene oxide (GO) as a metal-free catalyst: Importance of dual catalytic activity
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A convenient and efficient process for the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles and 2,4,6-triarylpyridines has been described using an inexpensive, environmentally benign, metal-free heterogeneous carbocatalyst, graphene oxide (GO). GO plays a dual role of an oxidizing agent and solid acid catalyst for synthesizing 1,2,4-oxadiazoles and triarylpyridines. This dual catalytic activity of GO is due to the presence of oxygenated functional groups which are distributed on the nanosheets of graphene oxide. A broad scope of substrate applicability and good sustainability is offered in this developed protocol. The results of a few control experiments reveal a plausible mechanism and the role of GO as a catalyst was confirmed by FTIR, XRD, SEM, and HR-TEM analysis.
- Basak, Puja,Dey, Sourav,Ghosh, Pranab
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p. 32106 - 32118
(2021/12/02)
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- Application of salicylic acid as an eco-friendly and efficient catalyst for the synthesis of 2,4,6-triaryl pyridine, 2-amino-3-cyanopyridine, and polyhydroquinoline derivatives
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In this study, three eco-friendly, efficient, and convenient protocols have been reported for one-pot synthesis of 2,4,6-triaryl pyridine, 2-amino-3-cyanopyridine, and polyhydroquinoline derivatives using salicylic acid as a catalyst under solvent-free condition. The reported protocols offer several significant advantages such as the application of a nontoxic, neutral, and cheap catalyst, environmentally friendly conditions, the easy isolation of products by filtering, short reaction times, simple methodology, and good yields.
- Roozifar, Majid,Hazeri, Nourallah,Faroughi Niya, Homayoun
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p. 1117 - 1129
(2021/02/26)
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- Method for synthesizing pyridine ring structure by utilizing cascade reaction of aldehyde, arylboronic acid and acetonitrile
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The invention discloses a method for synthesizing a pyridine ring structure by utilizing cascade reaction of aldehyde, arylboronic acid and acetonitrile, which comprises the following steps: dissolving a palladium catalyst, aldehyde, arylboronic acid, a l
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Paragraph 0028-0031; 0032-0034; 0036; 0044-0045
(2021/06/12)
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- Method for synthesizing polysubstituted pyridine derivative based on oxime ester and unsaturated ketone under catalysis of ferric salt
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The invention belongs to the technical field of organic synthesis, and particularly relates to a method for synthesizing a polysubstituted pyridine derivative based on oxime ester and unsaturated ketone under the catalysis of ferric salt. For the first ti
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Paragraph 0074-0077
(2020/06/02)
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- Design and application of (Fe3O4)-GOTfOH based AgNPs doped starch/PEG-poly (acrylic acid) nanocomposite as the magnetic nanocatalyst and the wound dress
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As a novel, recyclable nanocatalyst, (Fe3O4)-GOTfOH based Ag nanoparticles doped Starch/PEG-poly (acrylic acid) nanocomposite (Fe3O4?GOTfOH/Ag/St-PEG-AcA) was applied for one-pot synthesis
- Forouzandehdel, Shayan,Meskini, Maryam,Rami, Mina Rezghi
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- An efficient, green solvent-free protocol for the synthesis of 2,4,6-triarylpyridines using reusable heterogeneous activated Fuller’s earth catalyst
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Abstract: A simple, efficient, and green method of preparation for the synthesis of highly substituted pyridines by multicomponent reaction of acetophenones, aldehydes, and ammonium acetate using activated Fuller’s earth as an effective and reusable heterogeneous catalyst is described. The advantages of the present protocol include simple procedure with an easy workup procedure, mild reaction conditions, and high yields of the products. The performance of this reaction under solvent-free conditions using heterogeneous catalysts, such as activated Fuller’s earth, could enhance its efficiency from an economic as well as ecological point of view. Graphical abstract: [Figure not available: see fulltext.].
- Rekunge, Deelip S.,Kale, Ishwari A.,Chaturbhuj, Ganesh U.
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p. 2455 - 2462
(2018/09/13)
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- Exploring the C^N^C theme: Synthesis and biological properties of tridentate cyclometalated gold(III) complexes
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A family of cyclometalated Au(III) complexes featuring a tridentate C^N^C scaffold has been synthesized and characterized. Microwave assisted synthesis of the ligands has also been exploited and optimized. The biological properties of the thus formed comp
- Jürgens, Sophie,Scalcon, Valeria,Estrada-Ortiz, Natalia,Folda, Alessandra,Tonolo, Federica,Jandl, Christian,Browne, Duncan L.,Rigobello, Maria Pia,Kühn, Fritz E.,Casini, Angela
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p. 5452 - 5460
(2017/10/06)
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- An Efficient Synthesis of 2,4,6-Triarylpyridines by Use of Benzyl Halides under Neat Conditions
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An efficient synthesis of 2,4,6-triarylpyridines is described. Heating a mixture of an acetophenone, a benzyl halide, and ammonium acetate under neat conditions afforded the corresponding Kr?hnke pyridines in excellent yields.
- Adib, Mehdi,Ayashi, Neda,Mirzaei, Peiman
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p. 417 - 421
(2016/02/09)
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- An improved and highly efficient one-pot three-component synthesis of 2,4,6-triarylpyridines catalyzed by melamine trisulfonic acid under solvent-free condition
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A facile one-pot synthesis of triarylpyridines as valuable products is reported via three-component condensation reaction in the presence of environmentally benign melamine trisulfonic acid (MTSA) under solvent-free condition. The present protocol offers several advantages including simple work-up procedure, high yields and ease of catalyst isolation with suitable recyclability.
- Mouradzadegun, Arash,Kiasat, Ali Reza,Asareh, Hadi
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p. 943 - 947
(2016/02/18)
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- One-pot, solvent-free and efficient synthesis of 2,4,6-triarylpyridines catalyzed by nano-titania-supported sulfonic acid as a novel heterogeneous nanocatalyst
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Nano titania-supported sulfonic acid (n-TSA) has found to be a highly efficient, eco-friendly and recyclable heterogeneous nanocatalyst for the solvent-free synthesis of 2,4,6-triarylpyridines through one-pot three-component reaction of acetophenones, aryl aldehydes and ammonium acetate. This reported method illustrates several advantages such as environmental friendliness reaction conditions, simplicity, short reaction time, easy work up, reusability of catalyst and high yields of the products. One new compound is reported too. Furthermore, the catalyst could be recycled after a simple work-up, and reused at least six times without substantial reduction in its catalytic activity.
- Tabrizian, Elham,Amoozadeh, Ali,Rahmani, Salman,Imanifar, Elham,Azhari, Saeede,Malmir, Masoumeh
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p. 1278 - 1282
(2015/12/31)
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- Nano-Fe3O4-supported, hydrogensulfate ionic liquid-catalyzed, one-pot synthesis of polysubstituted pyridines
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Anchoring 1-methyl-3-(triethoxysilylpropyl) imidazolium chloride onto silica-coated magnetic Fe3O4 particles afforded the corresponding supported ionic liquid. Exchanging the Cl- anion by treating with H2SO4 gave Br?nsted ionic liquid 1-methyl-3-(triethoxysilylpropyl) imidazolium hydrogensulfate. The synthesized catalyst was characterized by various techniques such as infrared, x-ray diffraction, scanning electron microscopy, thermogravimetric analysis, and elemental analyses. The results indicated that the prepared catalyst had a nanostructure. The catalytic activity of the supported ionic liquid was examined in the synthesis of the polysubstituted pyridines by reaction of aromatic aldehydes with acetophenones and ammonium acetate in moderate to good yields under solvent-free conditions. The catalyst can be easily recovered by applying an external magnetic field and reused for at least seven runs without deterioration in catalytic activity.
- Alinezhad, Heshmatollah,Tajbakhsh, Mahmood,Ghobadi, Neda
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supporting information
p. 1964 - 1976
(2015/08/18)
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- The synthesis of polysubstituted pyridines using nano Fe3O4 supported hydrogensulfate ionic liquid
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Reaction of 1-methylimidazole with 3-(trimethoxysilyl)propyl chloride resulted in formation of 1-methyl-3-(trimethoxysilyl)propyl imidazolium chloride ([pmim]Cl). Anchoring of the ionic liquid on to silica-coated magnetic Fe3O4 particles afforded the corresponding supported ionic liquid MNP-[pmim]Cl. Exchanging the Cl- anion by treatment with H2SO4 gave the Bronsted ionic liquid MNP-[pmim]HSO4. FT-IR, XRD, SEM, TEM, TG/DTG, VSM, and CHN analysis were used to characterize the supported ionic liquid. The results indicated the catalyst was a nanostructure. The catalytic activity of the supported ionic liquid was examined in the synthesis of the polysubstituted pyridines by reaction of aromatic aldehydes, and acetophenones or indan-1-one with ammonium acetate under solvent-free conditions. The catalyst could be easily recovered, by applying an external magnetic field, and reused at least six runs without deterioration of its catalytic activity.
- Alinezhad, Heshmatollah,Tajbakhsh, Mahmood,Ghobadi, Neda
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p. 9113 - 9127
(2015/10/28)
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- An efficient synthesis of 2,4,6-triarylpyridines via solvent-free reaction between acetophenoneoximes and aldehydes
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An efficient synthesis of 2,4,6-triarylpyridines is described. Heating a mixture of an acetophenoneoxime and an aldehyde under solvent-free conditions afforded Kr?hnke pyridines in excellent yields. In this method acetophenoneoximes are directly used for the preparation of Kr?hnke pyridines under metal-free conditions. Georg Thieme Verlag Stuttgart New York.
- Mahernia, Shabnam,Mahdavi, Mohammad,Adib, Mehdi
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- A facile one-pot synthesis of 2,4,6-triarylpyridine in DMSO
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A facile, efficient and practical method for the one-pot synthesis of 2,4,6-triarylpyridines starting from acetophenones, aryl aldehydes and ammonium acetate by the use of catalytic amounts of 40 % potassium hydroxide in dimethyl sulfoxide is presented. T
- Min, Zhen-Li,Yin, Ting-Zi,Hu, Xia-Min
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p. 7977 - 7980
(2015/02/02)
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- A solvent-free reaction between acetophenone oximes and epoxy styrenes: An efficient synthesis of 2,4,6-triarylpyridines under neutral conditions
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An efficient synthesis of 2,4,6-triarylpyridines is described which involves heating a mixture of an acetophenone oxime and an epoxy styrene under neutral, solvent-free conditions. Kr?hnke pyridine products are obtained in excellent yields.
- Mahernia, Shabnam,Adib, Mehdi,Mahdavi, Mohammad,Nosrati, Meisam
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p. 3844 - 3846
(2014/07/08)
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- Bismuth triflate catalyzed solvent-free synthesis of 2,4,6-triaryl pyridines and an unexpected selective acetalization of tetrazolo[1,5-a]- quinoline-4-carbaldehydes
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Bismuth triflate has been found as a potential catalyst for an efficient and solvent-free synthesis of symmetrical 2,4,6-triarylpyridines in 86-93% yields. Moreover, catalytic reactivity of bismuth triflate toward tetrazolo[1,5-a]quinoline-4-carbaldehydes
- Shinde, Pravin V.,Labade, Vilas B.,Gujar, Jitendra B.,Shingate, Bapurao B.,Shingare, Murlidhar S.
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experimental part
p. 1523 - 1527
(2012/03/27)
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- Highly efficient and easy synthesis of 2,4,6-triarylpyridines catalyzed by pentafluorophenylammonium triflate (PFPAT) as a new recyclable solid acid catalyst in solvent-free conditions
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Pentafluorophenylammonium triflate (PFPAT) was found to be a highly efficient catalyst for the preparation of 2,4,6-triarylpyridines from the reaction of acetophenone derivatives, aromatic aldehydes and ammonium acetate. Present methodology offers several advantages, such as short reaction time, high yields, simple procedure with an easy work-up and the absence of any volatile and hazardous organic solvent. In addition, this catalytic system can act as an active, inexpensive, metal-free, recoverable and recyclable catalyst.
- Montazeri, Naser,Mahjoob, Saber
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experimental part
p. 419 - 422
(2012/06/18)
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- Silica gel-supported poly phosphoric acid catalyzed one-pot multi-component synthesis of 2,4,6-Triarylpyridines under solvent-free and microwave irradiation conditions
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A simple, green and efficient protocol is developed in which silica gel-supported poly phosphoric acid (PPA-SiO2) is employed as a solid acid catalyst in solvent-free and microwave irradiation conditions for the synthesis of various 2,4,6-triarylpyridines
- Montazeri, Naser,Pourshamsian, Khalil,Kalantarian, Roya,Kia, Mohammad Mehdi
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experimental part
p. 3751 - 3753
(2012/07/27)
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- Green, new and efficient tandem oxidation and conversion of aryl alcohols to 2,4,6-triarylpyridines promoted by [HMIm]NO3-[BMIm]BF4 as a binary ionic liquid
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A novel, clean and efficient tandem process has been established for the synthesis of 2,4,6-triarylpyridines from primary aryl alcohols or 1-arylethanols using 1-methylimidazolium nitrate in 1-butyl-3-methylimidazolium tetrafluoroborate as a binary task-specific ionic liquid under microwave irradiation.
- Khosropour, Ahmad R.,Mohammadpoor-Baltork, Iraj,Kiani, Forough
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experimental part
p. 441 - 445
(2012/03/22)
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- Synthesis of unsymmetrical polysubstituted pyridines from β-sulfonylvinylamines via 1-aza-allyl anion intermediates
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A modular synthesis of highly functionalized unsymmetrical pyridines has been developed from reacting β-sulfonylvinylamines with α,β-unsaturated systems in the presence of base via the formation of 1-aza-allyl anion intermediates. Georg Thieme Verlag Stut
- Lau, Chan,Tsui, Gavin Chit,Lautens, Mark
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p. 3908 - 3914
(2012/01/11)
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- Copper-Catalyzed coupling of oxime acetates with aldehydes: A new strategy for synthesis of pyridines
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Copper-catalyzed coupling of oxime acetates with aldehydes offers a new strategy for the synthesis of highly substituted pyridines. This novel method tolerates a wide range of functionality and allows for rapid elaboration of the oxime acetates into a variety of substituted pyridines.
- Ren, Zhi-Hui,Zhang, Zhi-Yuan,Yang, Bing-Qin,Wang, Yao-Yu,Guan, Zheng-Hui
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supporting information; experimental part
p. 5394 - 5397
(2011/12/02)
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- Solvent-free, one-pot synthesis of 2,4,6-triarylpyridines using trichloroisocyanuric acid or N-bromosuccinimide as a novel and neutral catalyst
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A simple and benign protocol has been explored for the preparation of 2,4,6-triarylpyridines by a one-pot reaction between aryl aldehydes, enolizable ketones and ammonium acetate in the presence of N-bromosuccinimide or trichloroisocyanuric acid as green and neutral catalysts. The reactions proceed smoothly at 130 °C under solvent-free conditions to provide 2,4,6-triarylpyridines in good yields.
- Maleki, Behrooz,Salehabadi, Hafezeh,Sepehr, Zeinalabedin,Kermanian, Mina
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experimental part
p. 1307 - 1315
(2012/04/04)
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- Highly efficient, one-pot, solvent-free synthesis of 2,4,6-triarylpyridines using a bronsted-acidic ionic liquid as reusable catalyst
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A simple, efficient, and green method for synthesis of 2,4,6- triarylpyridines by one-pot three-component reaction of acetophenones, aryl aldehydes, and ammonium acetate using 3-methyl-1-(4-sulfonylbutyl)imidazolium hydrogen sulfate [HO3S(CH2)4MIM][HSO 4], a Bronstedacidic ionic liquid, as an effective and reusable catalyst under solvent-free conditions is described. This method has several advantages, for example simple procedure with an easy work-up, shorter reaction times, and high yields. Springer-Verlag 2010.
- Davoodnia, Abolghasem,Bakavoli, Mehdi,Moloudi, Raheleh,Tavakoli-Hoseini, Niloofar,Khashi, Maryam
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experimental part
p. 867 - 870
(2011/06/26)
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- Three-components condensation catalyzed by molecular iodine for the synthesis of 2,4,6-triarylpyridines and 5-unsubstituted-3,4-dihydropyrimidin- 2(1H)-ones under solvent-free conditions
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One-pot, three-components synthesis of 2,4,6-triarylpyridines and 5-unsubstituted-3,4-dihydropyrimidin-2(1H)-ones was performed under solvent-free conditions using molecular iodine as the catalyst in moderate to good product yields.
- Ren, Yi-Ming,Cai, Chun
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experimental part
p. 49 - 52
(2010/04/06)
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- Reaction between guanidine hydroehloride and chalcones: An efficient solvent-free synthesis of 2,4,6-triarylpyridines under microwave irradiation
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A series of 2,4,6-triarylpyridines have been synthesized via an efficient solvent-free reaction between guanidine hydro-chloride and chalcones under microwave irradiation in excellent yields. Copyright
- Adib, Mehdi,Mohammadi, Bagher,Rahbari, Sahar,Mirzaei, Peiman
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scheme or table
p. 1048 - 1049
(2009/12/02)
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- Novel solid-supported dimerization-heteroannulation of chalcones: simple and efficient synthesis of 2,4,6-triaryl-3-methylarylpyridines
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2,4,6-Triaryl-3-methylarylpyridines were obtained, in 60-70% yield, by a novel one-pot solventless solid-supported dimerization-heteroannulation reaction of chalcones and compounds possessing terminal -CONH2 functionality, at 125-135 °C, using immobilized Bi(III) nitrate and Zn(II) chloride as co-catalyst. Initially, chalcones were prepared, in nearly quantitative yield, by a modified aldol condensation, in neutral aqueous medium, in the presence of p-toluenesodium sulfonate.
- Verma, Anil K.,Koul, Summon,Pannu, Ajay P.S.,Razdan, Tej K.
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p. 8715 - 8722
(2008/02/10)
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- Kr?hnke pyridines: an efficient solvent-free synthesis of 2,4,6-triarylpyridines
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A simple and efficient synthesis of 2,4,6-triarylpyridines is described from a novel reaction between chalcones and ammonium acetate under solvent-free conditions in excellent yields.
- Adib, Mehdi,Tahermansouri, Hasan,Koloogani, Somayeh Aali,Mohammadi, Bagher,Bijanzadeh, Hamid Reza
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p. 5957 - 5960
(2007/10/03)
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- Kinetics and Mechanisms of Nucleophilic Displacements with Heterocycles as Leaving Groups. Part 4. 2,4,6-Triaryl-N-benzylpyridinium Cations: Rate Variation with Electronic Effects in the Leaving Group
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Electron-withdrawing groups in the 4-phenyl ring of 2,4,6-triphenylpyridine modestly increase its activity as a leaving group.Replacement of 2-phenyl by heteroaryl has a small effect for monoheteroaryl groups, but significantly larger for 2-benzimidazol-2-yl and especially for 2-benzothiazol-1-yl.
- Katritzky, Alan R.,Adamson, Jeffrey,Elisseou, E. Michael,Musumarra, Giuseppe,Patel, Ranjan C.,et al.
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p. 1041 - 1048
(2007/10/02)
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