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Journal articles on the topic 'Pyrrolo (3,2-C) Pyridine(Methyl-1)'

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Published: 4 June 2021

Last updated: 10 February 2022

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1

Karpov, Sergey, Arthur Grigor’ev, Yakov Kayukov, Iuliia Gracheva, and Victor Tafeenko. "Cascade Regioselective Heterocyclization of 2-Acyl-1,1,3,3-tetracyanopropenides: Synthesis of Pyrrolo[3,4-c]pyridine and Pyrrolo[3,4-d]thieno[2,3-b]pyridine Derivatives." Synlett 28, no. 13 (2017): 1592–95. http://dx.doi.org/10.1055/s-0036-1588823.

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2-Acyl-1,1,3,3-tetracyanopropenides (ATCN) undergo cascade heterocyclization under the action of aliphatic thiols, resulting in the formation of 6-(alkylthio)-4-amino-1-aryl(alkyl)-1-hydroxy-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitriles. The involvement of methyl mercaptoacetate to this reaction leads to the formation of the methyl 4,8-diamino-1-aryl-1-hydroxy-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-d]thieno[2,3-b]pyridine-7-carboxylates, containing a new fused heterocyclic scaffold.

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2

Meade, Eric A., and Lilia M. Beauchamp. "The synthesis of 4-benzylamino-6-methyl-1H-pyrrolo[3, 2-c]pyridine and 4-benzylamino-6-methyl-1H-pyrrolo[2, 3-b]pyridine." Journal of Heterocyclic Chemistry 33, no. 2 (1996): 303–8. http://dx.doi.org/10.1002/jhet.5570330215.

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3

Mosiagin, Ivan P., Olesya A. Tomashenko, Dar’ya V. Spiridonova, Mikhail S. Novikov, Sergey P. Tunik, and Alexander F. Khlebnikov. "Free-radical cyclization approach to polyheterocycles containing pyrrole and pyridine rings." Beilstein Journal of Organic Chemistry 17 (June 23, 2021): 1490–98. http://dx.doi.org/10.3762/bjoc.17.105.

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A wide range of derivatives with new pyrido[2,1-a]pyrrolo[3,4-c]isoquinoline skeleton was synthesized by free-radical intramolecular cyclization of o-bromophenyl-substituted pyrrolylpyridinium salts using the (TMS)3SiH/AIBN system. The cyclization provides generally good yields of pyrido[2,1-a]pyrrolo[3,4-c]isoquinoline hydrobromides having no additional radical-sensitive substituents. The free bases can be obtained from the synthesized hydrobromides in quantitative yield by basification at room temperature. The selectivity control of intramolecular arylation was achieved by replacing the halo

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4

Brimble, MA, MT Brimble, R. Hodges, and GA Lane. "Synthesis of 2-Methylpyrrolo[1,2-a]pyrazin-1(2h)-one." Australian Journal of Chemistry 41, no. 10 (1988): 1583. http://dx.doi.org/10.1071/ch9881583.

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The synthesis of 2-methylpyrrolo[1,2-a]pyrazin-1(2H)-one (2) present in the insect feeding deterrent peramine (1) through oxidation of the saturated lactam (3) is described. The preparation of the related 6- methyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one (12) through a Lewis-acid- catalysed cyclization of the amide acetal (7) is also described.

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5

Lessing, Timo, and Thomas Müller. "One-Pot Coupling–Cyclization–Alkylation Synthesis of 1,2,5-Trisubstituted 7-Azaindoles in a Consecutive Three-component Fashion." Synlett 28, no. 14 (2017): 1743–47. http://dx.doi.org/10.1055/s-0036-1590837.

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1,2,5-Trisubstituted 7-azaindoles are rapidly and efficiently prepared in a one-pot, copper-free alkynylation–cyclization–alkylation sequence starting from unprotected 2-aminopyridyl halides in a consecutive three-component fashion. By extension to a consecutive four-component coupling–cyclization–iodination–alkylation synthesis of 3-iodo-1-methyl-2-phenyl-1H-pyrrolo[2,3-b]pyridine, a concise synthesis of SIS3, a selective TGF-β1 and signaling inhibitor, was realized.

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6

Melekhina, Valeriya G., Andrey N. Komogortsev, Boris V. Lichitsky, et al. "One-pot synthesis of substituted pyrrolo[3,4-b]pyridine-4,5-diones based on the reaction of N-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-arylethyl)acetamide with amines." Beilstein Journal of Organic Chemistry 15 (November 25, 2019): 2840–46. http://dx.doi.org/10.3762/bjoc.15.277.

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The condensation of primary amines with N-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-arylethyl)acetamides was explored. Thus, a previously unknown recyclization of the starting material was observed in acidic ethanol in the presence of an amine, which provided the corresponding dihydropyrrolone derivative as the major reaction product. Based on this transformation, a practical and convenient one-pot synthetic method for substituted pyrrolo[3,4-b]pyridin-5-ones could be devised.

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7

Śladowska, Helena, Barbara Filipek, Dominika Szkatuła, et al. "Investigations on the synthesis and pharmacological properties of 4-alkoxy-2-[2-hydroxy-3-(4-aryl-1-piperazinyl)propyl]-6-methyl-1H-pyrrolo[3,4-c]pyridine-1,3(2H)-diones." Il Farmaco 57, no. 11 (2002): 897–908. http://dx.doi.org/10.1016/s0014-827x(02)01302-2.

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8

Muszalska, Izabela. "Kinetics of hydrolysis of 4-methoxy-2-[2-hydroxy-3(4-phenyl-1-piperazinyl)]propyl-2,3-dihydro-6-methyl-1,3-dioxo-1H-pyrrolo[3,4-c]pyridine in aqueous solutions." Il Farmaco 59, no. 6 (2004): 437–42. http://dx.doi.org/10.1016/j.farmac.2004.02.007.

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9

George, M., S. Das, C. V. Ashokan, N. P. Rath, and M. V. George. "2-Phenyl-3-(5,6,7,7a-tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-ylidene)-1-propene-1,1-dicarbonitrile and 4-(4-Methoxyphenyl)-2,6-bis(methylthio)pyridine-3-carbonitrile." Acta Crystallographica Section C Crystal Structure Communications 54, no. 7 (1998): 1033–36. http://dx.doi.org/10.1107/s0108270197018398.

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10

Krzyżak, Edward, Dominika Szkatuła, Benita Wiatrak, Tomasz Gębarowski, and Aleksandra Marciniak. "Synthesis, Cyclooxygenases Inhibition Activities and Interactions with BSA of N-substituted 1H-pyrrolo[3,4-c]pyridine-1,3(2H)-diones Derivatives." Molecules 25, no. 12 (2020): 2934. http://dx.doi.org/10.3390/molecules25122934.

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Inhibition of cyclooxygenase is the way of therapeutic activities for anti-inflammatory pharmaceuticals. Serum albumins are the major soluble protein able to bind and transport a variety of exogenous and endogenous ligands, including hydrophobic pharmaceuticals. In this study, a novel N-substituted 1H-pyrrolo[3–c]pyridine-1,3(2H)-diones derivatives were synthesized and biologically evaluated for their inhibitory activity against cyclooxygenases and interactions with BSA. In vitro, COX-1 and COX-2 inhibition assays were performed. Interaction with BSA was studied by fluorescence spectroscopy an

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11

GEORGE, M., S. DAS, C. V. ASHOKAN, N. P. RATH, and M. V. GEORGE. "ChemInform Abstract: 2-Phenyl-3-(5,6,7,7a-tetrahydro-1H,3H-pyrrolo [1,2-c]oxazol-3-ylidene)-1-propene-1,1-dicarbonitrile and 4-(4-Methoxyphenyl)-2,6-bis(methylthio)pyridine-3-carbonitrile." ChemInform 29, no. 47 (2010): no. http://dx.doi.org/10.1002/chin.199847035.

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12

Muszalska, Izabela, Helena Śadowska, and Dominika Szkatula. "A validated spectrophotometric and liquid chromatography method for determination and purity evaluation of 4-methoxy-2-[2-hydroxy-3(4-phenyl-1-piperazinyl)]propyl-2,3-dihydro-6-methyl-1,3-dioxo-1H-pyrrolo[3,4-c]pyridine." Il Farmaco 58, no. 7 (2003): 513–19. http://dx.doi.org/10.1016/s0014-827x(03)00062-4.

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13

Vishnupriya, R., M. Venkateshan, J. Suresh, R. V. Sumesh, R. Ranjith Kumar, and P. L. Nilantha Lakshman. "Crystal structure of 7′-(4-chlorophenyl)-2′′-(4-methoxyphenyl)-7′,7a',7′′,8′′-tetrahydro-1′H,3′H,5′′H-dispiro[indoline-3,5′-pyrrolo[1,2-c]thiazole-6′,6′′-quinoline]-2,5′′-dione and an unknown solvent." Acta Crystallographica Section E Crystallographic Communications 75, no. 2 (2019): 189–93. http://dx.doi.org/10.1107/s2056989019000112.

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The asymmetric unit of the title compound, C34H28ClN3O3S, contains two independent molecules (A and B). They differ essentially in the orientation of the 4-methoxyphenyl ring with respect to the pyridine ring of the quinoline moiety; this dihedral angle is 37.01 (18)° in molecule A but only 7.06 (17)° in molecule B. In both molecules, the cyclohexanone ring of the isoquinoline unit has a half-chair conformation. In the pyrrolothiazole ring system, the pyrrolo ring in molecule A has a twisted conformation on the N—C fused bond and an envelope conformation in molecule B with the N atom as the fl

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14

Muszalska, Izabela, and Szymon Bereda. "Stability Study of New Analgesic Active Compound, 4‐Methoxy‐2‐[3‐[4‐(2‐methoxyphenyl)‐1‐piperazinyl)]‐propyl] Derivative of Pyrrolo[3,4‐c]pyridine, in Aqueous Solutions Using the HPLC Method." Journal of Liquid Chromatography & Related Technologies 31, no. 7 (2008): 1001–13. http://dx.doi.org/10.1080/10826070801924832.

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15

Khlebnikov, Alexander, Liya Funt, Olesya Tomashenko, and Mikhail Novikov. "An Azirine Strategy for the Synthesis of Alkyl 4-Amino-5-(trifluoromethyl)-1H-pyrrole-2-carboxylates." Synthesis 50, no. 24 (2018): 4809–22. http://dx.doi.org/10.1055/s-0037-1610840.

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1-(3,3,3-Trifluoro-2,2-dihydroxypropyl)pyridin-1-ium bromide serves as a trifluoromethyl-containing building block for the preparation of trifluoromethyl-substituted aminopyrroles based on the 2H-azirine ring expansion strategy. The primary products, 3-aryl-2-(methoxycarbonyl)-4-(pyridin-1-ium-1-yl)-5-(trifluoromethyl)pyrrol-1-ides, can be hydrogenated by H2/PtO2 to form alkyl 3-aryl-4-(piperidin-1-yl)-5-(trifluoromethyl)-1H-pyrrole-2-carboxylates and transformed into alkyl 4-amino-3-aryl-1-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylates via methylation/hydrazinolysis.

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16

Tomashenko, Olesya A., Alexander F. Khlebnikov, Ivan P. Mosiagin, et al. "A new heterocyclic skeleton with highly tunable absorption/emission wavelength via H-bonding." RSC Advances 5, no. 115 (2015): 94551–61. http://dx.doi.org/10.1039/c5ra17755c.

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A new heterocyclic system, pyrido[2,1-a]pyrrolo[3,2-c]isoquinoline, showing stimuli responsive fluorescence, was synthesized via Pd-catalyzed intramolecular cyclization of 1-[1-benzyl-2-(2-bromophenyl)-1H-pyrrol-3-yl]pyridin-1-ium bromides.

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17

Park, Yu Mi, Markus R. Meyer, Rolf Müller, and Jennifer Herrmann. "Drug Administration Routes Impact the Metabolism of a Synthetic Cannabinoid in the Zebrafish Larvae Model." Molecules 25, no. 19 (2020): 4474. http://dx.doi.org/10.3390/molecules25194474.

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Zebrafish (Danio rerio) larvae have gained attention as a valid model to study in vivo drug metabolism and to predict human metabolism. The microinjection of compounds, oligonucleotides, or pathogens into zebrafish embryos at an early developmental stage is a well-established technique. Here, we investigated the metabolism of zebrafish larvae after microinjection of methyl 2-(1-(5-fluoropentyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxamido)-3,3-dimethylbutanoate (7′N-5F-ADB) as a representative of recently introduced synthetic cannabinoids. Results were compared to human urine data and data from the

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18

Tozzi, Alessandro, Ezia Guatteo, Luigi Caputi, Giorgio Bernardi, and Nicola B. Mercuri. "Group I mGluRs Coupled to G Proteins Are Regulated by Tyrosine Kinase in Dopamine Neurons of the Rat Midbrain." Journal of Neurophysiology 85, no. 6 (2001): 2490–97. http://dx.doi.org/10.1152/jn.2001.85.6.2490.

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Metabotropic glutamate receptors (mGluRs) modulate neuronal function via different transduction mechanisms that are either dependent or independent on G-protein function. Here we investigated, using whole cell patch-clamp recordings in combination with fluorimetric measurements of intracellular calcium concentration ([Ca2+]i), the metabolic pathways involved in the responses induced by group I mGluRs in dopamine neurons of the rat midbrain. The inward current and the [Ca2+]i increase caused by the group I mGluR agonist ( S)-3,5-dihydroxyphenylglycine (DHPG, 100 μM) were permanently activated a

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19

Nagy, Sándor, András Ozsváth, Attila Cs Bényei, Etelka Farkas, and Péter Buglyó. "Donor Atom Preference of Organoruthenium and Organorhodium Cations on the Interaction with Novel Ambidentate (N,N) and (O,O) Chelating Ligands in Aqueous Solution." Molecules 26, no. 12 (2021): 3586. http://dx.doi.org/10.3390/molecules26123586.

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Two novel, pyridinone-based chelating ligands containing separated (O,O) and (Namino,Nhet) chelating sets (Namino = secondary amine; Nhet = pyrrole N for H(L3) (1-(3-(((1H-pyrrole-2-yl)methyl)-amino)propyl)-3-hydroxy-2-methylpyridin-4(1H)-one) or pyridine N for H(L5) (3-hydroxy-2-methyl-1-(3-((pyridin-2-ylmethyl)amino)propyl)pyridin-4(1H)-one)) were synthesized via reduction of the appropriate imines. Their proton dissociation processes were explored, and the molecular structures of two synthons were assessed by X-ray crystallography. These ambidentate chelating ligands are intended to develop

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20

Macías, Mario A., Juan-Carlos Castillo, and Jaime Portilla. "A series of (E)-5-(arylideneamino)-1-tert-butyl-1H-pyrrole-3-carbonitriles and their reduction products to secondary amines: syntheses and X-ray structural studies." Acta Crystallographica Section C Structural Chemistry 74, no. 1 (2018): 82–93. http://dx.doi.org/10.1107/s2053229617017260.

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An efficent access to a series of N-(pyrrol-2-yl)amines, namely (E)-1-tert-butyl-5-[(4-chlorobenzylidene)amino]-1H-pyrrole-3-carbonitrile, C16H16ClN3, (7a), (E)-1-tert-butyl-5-[(2,4-dichlorobenzylidene)amino]-1H-pyrrole-3-carbonitrile, C16H15Cl2N3, (7b), (E)-1-tert-butyl-5-[(pyridin-4-ylmethylene)amino]-1H-pyrrole-3-carbonitrile, C15H16N4, (7c), 1-tert-butyl-5-[(4-chlorobenzyl)amino]-1H-pyrrole-3-carbonitrile, C16H18ClN3, (8a), and 1-tert-butyl-5-[(2,4-dichlorobenzyl)amino]-1H-pyrrole-3-carbonitrile, C16H17Cl2N3, (8b), by a two-step synthesis sequence (solvent-free condensation and reduction)

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21

Kubík, Richard, Stanislav Böhm, Iveta Ruppertová, and Josef Kuthan. "Sterically Crowded Heterocycles. III. A General Approach to Imidazo[1,2-a]pyridines by Ferricyanide Oxidation of Quaternary Pyridinium Salts." Collection of Czechoslovak Chemical Communications 61, no. 1 (1996): 126–38. http://dx.doi.org/10.1135/cccc19960126.

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Substituted 1-(pyridin-2-yl)-2,4,6-triphenylpyridinium perchlorates 1b-1e were converted with potassium ferricyanide and potassium hydroxide to sterically crowded 2-phenyl-3-[(Z)-1,3-diphenyl-3-oxopropenyl]imidazo[1,2-a]pyridines 2b-2e accompanied by minor isomeric 2-benzoyl-3,5-diphenyl-1-(pyridin-2-yl)pyrroles 3c-3e. 4-Phenyl-2,6-di(4-substituted phenyl)-1-(pyridin-2-yl)pyridinium salts 4a, 4b gave exclusively corresponding imidazo[1,2-a]pyridines 5a, 5b while the ferricyanide oxidation of 1-(5-iodo- and 5-cyanopyridin-2-yl)-2,4,6-triphenylpyridinium perchlorates 6a, 6b led to mixtures of ma

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22

Giubellina, Nicola, Wim Aelterman, and Norbert De Kimpe. "Use of 3-halo-1-azaallylic anions in heterocyclic chemistry." Pure and Applied Chemistry 75, no. 10 (2003): 1433–42. http://dx.doi.org/10.1351/pac200375101433.

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The synthetic potential of lithio 3-halo-1-azaallylic anions as building blocks in organic chemistry and especially in heterocyclic chemistry will be highlighted by the synthesis of functionalized imines, obtained after reaction of 3-halo-1-azaallylic anions with het- eroatom-substituted electrophiles. Thus, the latter generated functionalized imines are suitable building blocks for the synthesis of a whole range of heterocycles and physiologically active compounds, including agrochemicals and pharmaceuticals. 3-Halo-1-azaallylic anions were used in the synthesis of N-alkyl-3,3-dichloroazetidi

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23

Horton, Peter N., Shaaban K. Mohamed, Ahmed M. Soliman, Eman M. M. Abdel-Raheem, and Mehmet Akkurt. "2-(Piperidin-1-yl)-6-(1H-pyrrol-1-yl)pyridine-3,5-dicarbonitrile." Acta Crystallographica Section E Structure Reports Online 68, no. 4 (2012): o938. http://dx.doi.org/10.1107/s1600536812008586.

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The piperidine ring of the title compound, C16H15N5, adopts a chair conformation. The pyridine ring is essentially planar, with a maximum deviation of 0.035 (3) Å. The pyrrole and pyridine rings are almost coplanar, forming a dihedral angle of 3.48 (14)°. In the crystal, no classical hydrogen bonds were found. In the crystal, the molecules are linked by aromatic π–π stacking [centroid–centroid separations = 3.4984 (16) and 3.9641 (15) Å between pyrrole and pyridine rings and between pyridine rings, respectively].

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24

Deeb, Ali, Besher Bayoumy, Fathy Yasine, and Rida Fikry. "Pyridazine Derivatives and Related Compounds, Part 4. Pyrrolo[2,3-c]pyridazines and Furo[2,3-c]pyndazines, Synthesis and Some Reactions." Zeitschrift für Naturforschung B 47, no. 3 (1992): 418–23. http://dx.doi.org/10.1515/znb-1992-0320.

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Ethyl 5-amino-3,4-diphenyl-7H-pyrrolo[2,3-c]pyridazine-6-carboxylate (1), ethyl 5-aminofuro[ 2,3-c]pyridazine-6-carboxylate (2) and 5-aminofuro[2,3-c]pyridazine-6-carboxamide (3), are obtained from 4-cyano-5,6-diphenyl-3(2H)-pyridazinone. 5-Acetamido and 5-chloroacetamido derivatives prepared from 1, undergo cyclization on heating to form 2-substituted pyridazino[4',3':4,5]pyrrolo[3,2-d]oxazin-4(5H)-one (5a, b). The reaction of 1 and 2 with hydrazine gave 6-carbohydrazide derivatives (7 a, b). Compound 3 undergoes condensation with acetyl chloride, chloroacetyl chloride, benzoyl chloride, form

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25

Ochmanska, Jolanta, and Peter G. Pickup. "Synthesis, electrochemistry, and ligand substitution reactions of conducting copolymer films of ruthenium polypyridine complexes and aromatic heterocycles." Canadian Journal of Chemistry 69, no. 4 (1991): 653–60. http://dx.doi.org/10.1139/v91-099.

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Conducting films containing ruthenium complexes of the general formula [Ru(2,2′-bipyridine)2(pmp)X]2+ (pmp = 3-(pyrrol-1-ylmethyl)pyridine, X = Cl−, ClO4−, pmp, CH3CN, or H2O) have been prepared by copolymerization of the Ru complex monomer with pyrrole, 3-methylthiophene, 1-methyl-3-(pyrrol-1-ylmethyl)pyridinium(1+), or 2,2′-bithiophene. The immobilized complexes exhibit rapid and reversible electrochemistry in acetonitrile. The perchlorate and water ligands are rapidly substituted to give the acetonitrile complex, while the chloride ligand is replaced more slowly. In aqueous media, both the

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26

Huang, Wenbo, Kaimei Wang, Ping Liu, Minghao Li, Shaoyong Ke та Yanlong Gu. "Three-component reactions of aromatic amines, 1,3-dicarbonyl compounds, and α-bromoacetaldehyde acetal to access N-(hetero)aryl-4,5-unsubstituted pyrroles". Beilstein Journal of Organic Chemistry 16 (30 листопада 2020): 2920–28. http://dx.doi.org/10.3762/bjoc.16.241.

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N-(Hetero)aryl-4,5-unsubstituted pyrroles were synthesized from (hetero)arylamines, 1,3-dicarbonyl compounds, and α-bromoacetaldehyde acetal by using aluminum(III) chloride as a Lewis acid catalyst through [1 + 2 + 2] annulation. This new versatile methodology provides a wide scope for the synthesis of different functional N-(hetero)aryl-4,5-unsubstituted pyrrole scaffolds, which can be further derived to access multisubstituted pyrrole-3-carboxamides. In the presence of 1.2 equiv of KI, a polysubstituted pyrazolo[3,4-b]pyridine derivative was also successfully synthesized.

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27

FAITA, G., G. POZZI, P. P. RIGHETTI, and G. TACCONI. "ChemInform Abstract: A Synthesis of 1-Methyl-2-oxo-3H-pyrrolo(2,3-c)pyridine." ChemInform 26, no. 23 (2010): no. http://dx.doi.org/10.1002/chin.199523147.

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28

Dollé, Frédéric, Sandrine Langle, Gaëlle Roger, et al. "Synthesis and In-Vivo Evaluation of [11C]p-PVP-MEMA as a PET Radioligand for Imaging Nicotinic Receptors." Australian Journal of Chemistry 61, no. 6 (2008): 438. http://dx.doi.org/10.1071/ch08083.

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Within the class of (4-pyridinyl)vinylpyridines developed by Abbott laboratories as potent neuronal nicotinic acetylcholine receptor ligands, p-PVP-MEMA ({(R)-2-[6-chloro-5-((E)-2-pyridin-4-ylvinyl)pyridin-3-yloxy]-1-methylethyl}methylamine) is the lead compound of a novel series that do not display the traditional nicotinic-like pyrrole-ring but still possessing high subnanomolar affinity (Ki 0.077 nm—displacement of [3H](–)cytisine from whole rat brain synaptic membranes). In the present study, p-PVP-MEMA and its nor-derivative ({(R)-2-[6-chloro-5-((E)-2-pyridin-4-ylvinyl)pyridin-3-yloxy]-1-

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29

Vadlakonda, Rajashekar, Sreenivas Enaganti, and Raghunandan Nerella. "INSILICO DISCOVERY OF HUMAN AURORA B KINASE INHIBITORS BY MOLECULAR DOCKING, PHARMACOPHORE VALIDATION AND ADMET STUDIES." Asian Journal of Pharmaceutical and Clinical Research 10, no. 2 (2017): 165. http://dx.doi.org/10.22159/ajpcr.2017.v10i2.14974.

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Objectives: To predict the anticancer potentiality of some newly designed azaindole derivatives gainst human Aurora B kinase and to identify the critical features important for their activity.Methods: Initially, the derivatives of azaindoles, (Z)-2-(oxo-1 H-pyrrolo [2,3-b] pyridine-3 (2H)-ylidene)-N-(p-substituted) hydrazine carbothioamide (scaffold A), (E)-3-((E)-substituted benzylidene hydrazono)-1H-pyrrolo[2,3-b]pyridine-2(3H)-one (scaffold B), and 1-(2-substituted acetyl)-1H- pyrrolo [2,3-b]pyridine-2,3-dione are synthesized and sketched using ACD/ChemSketch (12.0). With the 3D converted c

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30

Kapoor, Kamini, Madhukar B. Deshmukh, Chetan S. Shripanavar, Vivek K. Gupta, and Rajni Kant. "Ethyl 2-{3-[(6-chloropyridin-3-yl)methyl]-2-(nitroimino)imidazolidin-1-yl}acetate." Acta Crystallographica Section E Structure Reports Online 68, no. 4 (2012): o987. http://dx.doi.org/10.1107/s160053681200918x.

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In the title compound, C13H16ClN5O4, the imidazole ring is in a slight envelope conformation. The dihedral angle between the pyridine ring and the four essentially planar atoms [maximum deviation 0.015 (2) Å] of the imidazole ring is 80.8 (1)°. In, the crystal, weak C—H...O and C—H...N hydrogen bonds are present. In addition, there are weak π–π stacking interactions between symmetry-related pyridine rings with a centroid–centroid distance of 3.807 (1) Å.

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31

Thorimbert, Serge, Candice Botuha, and Kevin Passador. "‘Heteroaromatic Rings of the Future’: Exploration of Unconquered Chemical Space." Synthesis 51, no. 02 (2018): 384–98. http://dx.doi.org/10.1055/s-0037-1611279.

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William Pitt and co-workers have created a virtual exploratory heterocyclic library ‘VEHICLe’ containing over 200 unconquered bicyclic heteroaromatic rings, synthetically feasible with potential medicinal interest. Since the publication of the 22 ‘heteroaromatic rings of the future’ by Pitt in 2009, 15 of them have been successfully synthesized as bicyclic or polycyclic forms and evaluated for applications in both biology and material science. This short review presents the critical synthesis associated with innovative synthetic methodologies of the synthetically conquered ring scaffolds from

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32

Kant, Rajni, Vivek K. Gupta, Kamini Kapoor, Chetan S. Shripanavar, and Kaushik Banerjee. "1-[(6-Chloropyridin-3-yl)methyl]imidazolidin-2-one." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (2012): o1939. http://dx.doi.org/10.1107/s1600536812023537.

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In the title molecule, C9H10ClN3O, the dihedral angle between the pyridine ring and imidazoline ring mean plane [maximum deviation = 0.031–(3) Å] is 76.2 (1)°. In the crystal, N—H...O hydrogen bonds link pairs of molecules to form inversion dimers. In addition, weak C—H...N hydrogen bonds and π–π stacking interactions between pyridine rings [centroid–centroid distance = 3.977 (2) Å] are observed.

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33

Pohl, Radek, Stanislav Böhm, and Josef Kuthan. "Sterically Crowded Heterocycles. X. A New Mechanistic Approach to the Ferricyanide Oxidation of 4,6'-Disubstituted 1-(Pyridin-2'-yl)-2,6-diphenylpyridinium Salts." Collection of Czechoslovak Chemical Communications 64, no. 8 (1999): 1274–94. http://dx.doi.org/10.1135/cccc19991274.

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The oxidations of the title perchlorates, bearing the sterically diverse 6'-substituents (H, Me, Et, i-Pr, n-Bu, t-Bu and Ph) in two series with the same 4-substituents (Ph and t-Bu) lead to pairs of isomeric 3',5-disubstituted (Z)-1'-phenyl-3'-(2-phenylimidazo[1,2-a]pyridin-3-yl)prop-2'- en-1'-ones and 3,6'-disubstituted [5-phenyl-1-(6'-pyridin-2'-yl)-1H-pyrrol-2-yl](phenyl)methanones except where the both variable substituents are t-Bu and then only pyrrolic product is formed. Considering steric interactions of the substituents in some intermediate and/or transition states a multistep mechan

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34

Galvez, Enrique, Isabel Iriepa, Antonio Lorente, Jose Miguel Mohedano, Feliciana Florencio, and Severino Garcia-Blanco. "Synthesis and structural study of aminals derived from 8-aminoquinoline and 1-aminonaphtalene." Canadian Journal of Chemistry 65, no. 4 (1987): 687–92. http://dx.doi.org/10.1139/v87-117.

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Reaction of 8-aminoquinoline with pyridine-2-carboxaldehyde (2), pyridine-3-carboxaldehyde (3), pyridine-4-carboxaldehyde (4), and benzaldehyde (5) yields the corresponding aminals or Schiff's bases according to reaction conditions; analogous results are obtained from the reaction of 1-amino-naphtalene with pyridine-2-carboxaldehyde (6). On the other hand, reaction of 8-aminoquinoline with thiophene-2-carboxaldehyde or pyrrole-2-carboxaldehyde yields neither the aminal nor the Schiff's base. Crystals of 4 (C24H19N5) belong to the triclinic space group [Formula: see text]. Cell dimensions are a

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35

Odabaşoğlu, Mustafa, and Orhan Büyükgüngör. "3-(6-Methyl-2-pyridylamino)isobenzofuran-1(3H)-one." Acta Crystallographica Section E Structure Reports Online 63, no. 11 (2007): o4348. http://dx.doi.org/10.1107/s1600536807049677.

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The crystal structure of the title compound, C14H12N2O2, is stabilized by intermolecular N—H...O and C—H...N hydrogen bonds and also by C—H...π and π–π [centroid–centroid distance 3.822 (1) Å and a plane-to-plane separation 3.697 Å] interactions. The N—H...O and C—H...N hydrogen bonds generate edge-fused R 2 1(6)R 4 4(24)R 2 1(6) ring motifs. The phthalide group is planar and oriented with respect to the pyridine ring at a dihedral angle of 83.21 (9)°.

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36

Al-Omar, Mohamed A., Abdel-Galil E. Amr, Hazem A. Ghabbour, Tze Shyang Chia, and Hoong-Kun Fun. "Methyl 2-{6-[(1-methoxy-1-oxopropan-2-yl)aminocarbonyl]pyridine-2-carboxamido}propanoate." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (2012): o1837—o1838. http://dx.doi.org/10.1107/s1600536812022258.

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In the title compound, C15H19N3O6, the amide planes are inclined at dihedral angles of 0.8 (6) and 12.1 (3)° with respect to the central pyridine ring. The mean planes of the corresponding methyl acetate groups form dihedral angles of 41.76 (13) and 86.48 (15)°, respectively with the mean plane of pyridine ring. A pair of weak intramolecular N—H...N hydrogen bonds generate an S(5)S(5) ring motif in the molecule. In the crystal, molecules are linked by N—H...O hydrogen bonds into [001] chains. The chains are cross-linked by C—H...O hydrogen bonds into layers lying parallel to bc plane. The crys

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37

Yu, Yang, Yuan Liu, Aoxia Liu, Hexin Xie, Hao Li, and Wei Wang. "Ligand-free Cu-catalyzed [3 + 2] cyclization for the synthesis of pyrrolo[1,2-a]quinolines with ambient air as a terminal oxidant." Organic & Biomolecular Chemistry 14, no. 31 (2016): 7455–58. http://dx.doi.org/10.1039/c6ob01316c.

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A ligand-free Cu-catalyzed [3 + 2] cycloaddition of ethyl 2-(quinolin-2-yl)acetates, ethyl 2-(isoquinolin-1-yl)acetates, and ethyl 2-(pyridin-2-yl)acetates with (E)-chalcones for a “one-pot” synthesis of pyrrolo[1,2-a]quinolines, pyrrolo[2,1-a]isoquinolines and indolizines has been developed.

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38

Shivaprasad, C. M., S. Madan Kumar, T. R. Swaroop, K. S. Rangappa, and N. K. Lokanath. "1-(4-Methylphenylsulfonyl)-2-{[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfanyl}-1H-1,3-benzimidazole." Acta Crystallographica Section E Structure Reports Online 69, no. 12 (2013): o1846. http://dx.doi.org/10.1107/s1600536813031899.

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In the title compound, C23H20F3N3O3S2, the benzoimidazole unit makes dihedral angles of 5.02 (1) and 76.42 (1)°, respectively, with the pyridine and methylbenzene rings; the dihedral angle between the pyridine and methylbenzene rings is 72.19 (1)°. In the crystal, molecules are connected by weak C—H...F, C—H...O and C—H...N hydrogen bonds. Weak C—H...π interactions and π–π stacking [centroid–centroid distance = 3.6485 (14) Å] are also observed. The overall packing shows a three-dimensional architecture. The crystal structure contains a void of 51 Å3, but no solvent molecule (hexane or ethyl ac

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39

Sreeja, P. B., M. Sithambaresan, N. Aiswarya, and M. R. Prathapachandra Kurup. "N′-[(1E)-1-(2-Fluorophenyl)ethylidene]pyridine-3-carbohydrazide." Acta Crystallographica Section E Structure Reports Online 70, no. 2 (2014): o115. http://dx.doi.org/10.1107/s1600536813035009.

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The title compound, C14H12FN3O, adopts anEconformation with respect to the azomethine double bond whereas the N and methyl C atoms are in aZconformation with respect to the same bond. The ketonic O and azomethine N atoms arecisto each other. The non-planar molecule [the dihedral angle between the benzene rings is 7.44 (11)°] exists in an amido form with a C=O bond length of 1.221 (2) Å. In the crystal, a bifurcated N—H...(O,N) hydrogen bond is formed between the amide H atom and the keto O and imine N atoms of an adjacent molecule, leading to the formation of chains propagating along theb-axis

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40

Kondo, Mitsuyo, Makiko Kawamoto, Atsushi Hasuoka, Masahiro Kajino, Nobuhiro Inatomi, and Naoki Tarui. "High-Throughput Screening of Potassium-Competitive Acid Blockers." Journal of Biomolecular Screening 17, no. 2 (2011): 177–82. http://dx.doi.org/10.1177/1087057111421004.

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H+,K+-ATPase is a key enzyme in the process of gastric acid secretion, and proton pump inhibitors (PPIs) have been accepted as one of the most effective treatments for peptic ulcer and gastroesophageal reflux disease. To discover a novel class of PPIs, the authors screened a low-molecular-weight compound library and identified two prospective acid blockers that were pyrrole derivatives. Both compounds inhibited H+,K+-ATPase in a reversible and potassium-competitive manner. These compounds led to the development of TAK-438 (1-[5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methyl

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41

Wang, Chuan-Qi, Xiao-Xia Wang, Xiao-Hu Liu, et al. "Crystal structure of methyl 4-methyl-2,5-di(pyridin-4-yl)-1H-pyrrole-3-carboxylate monohydrate C17H15N3O2⋅H2O." Zeitschrift für Kristallographie - New Crystal Structures 234, no. 1 (2018): 113–14. http://dx.doi.org/10.1515/ncrs-2018-0216.

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AbstractC17H15N3O2⋅H2O, triclinic, P1̄ (no. 2), a = 5.7965(14) Å, b = 11.625(3) Å, c = 12.315(3) Å, α = 76.216(18)°, β = 76.674(18)°, β = 79.158(18)° V = 776.4(3) Å3, Z = 2, Rgt(F) = 0.0608, wRref(F2) = 0.1574, T = 113 K.

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42

Anantharaj, Ramalingam, and Tamal Banerjee. "Physiochemical Properties of Hydrodenitrification and Hydrodesulphurization Inhibiting Compounds with 1-Ethyl-3-Methylimidazolium Ethylsulphate at T = (298.15 to 323.15) K and Bar." Journal of Thermodynamics 2011 (May 25, 2011): 1–14. http://dx.doi.org/10.1155/2011/978324.

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This work investigates the ability of 1-ethyl-3-methylimidazolium ethylsulphate ([emim][EtSO4]) as a green and tuneable solvent for denitrification and desulphurization of diesel oil. Experimental density, surface tension, and refractive index data have been measured for the following systems: [emim][EtSO4](1) + pyridine(2), [emim][EtSO4](1)+ pyrrole(2), [emim][EtSO4](1) + quinoline(2), [emim][EtSO4](1) + indoline(2), [emim][EtSO4](1) + thiophene(2), and [emim][EtSO4](1) + water(2) over the entire mole fraction of [emim][EtSO4] at temperatures of (298.15 to 323.15) K and at atmospheric pressur

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43

Chidan Kumar, C. S., Ai Jia Sim, Weng Zhun Ng, et al. "The crystal structure of zwitterionic 2-{[(4-iminiumyl-3-methyl-1,4-dihydropyridin-1-yl)methyl]carbamoyl}benzoate hemihydrate." Acta Crystallographica Section E Crystallographic Communications 73, no. 7 (2017): 927–31. http://dx.doi.org/10.1107/s2056989017007836.

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The asymmetric unit of the title compound, C15H15N3O3·0.5H2O, comprises two 2-{[(4-iminiumyl-3-methyl-1,4-dihydropyridin-1-yl)methyl]carbamoyl}benzoate zwitterions (AandB) and a water molecule. The dihedral angles between the pyridine and phenyl rings in the zwitterions are 53.69 (10) and 73.56 (11)° inAandB, respectively. In the crystal, molecules are linked by N—H...O, O—H...O, C—H...O and C—H...π(ring) hydrogen bonds into a three-dimensional network. The crystal structure also features π–π interactions involving the centroids of the pyridine and phenyl rings [centroid–centroid distances = 3

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44

Saeedian Moghadam, Ebrahim, and Mohsen Amini. "2-[2-Methyl-5-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-pyrrol-3-yl]-2-oxo-N-(pyridin-4-yl) acetamide." Molbank 2018, no. 3 (2018): 1002. http://dx.doi.org/10.3390/m1002.

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45

Vimala, G., N. Poomathi, Y. AaminaNaaz, P. T. Perumal, and A. SubbiahPandi. "Crystal structure of 5-(5-chloro-2-hydroxybenzoyl)-2-(2-methyl-1H-indol-3-yl)nicotinonitrile." Acta Crystallographica Section E Crystallographic Communications 71, no. 11 (2015): o822—o823. http://dx.doi.org/10.1107/s2056989015018058.

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In the title compound, C22H14ClN3O2, the indole unit is essentially coplanar, with a maximum deviation of 0.035 Å for the C atom bearing the methyl group. The central pyridine ring is inclined to the indole ring system by 43.7 (1)°. The dihedral angle between the phenyl ring and the indole ring system is 15.7 (2)°, while that between the phenyl ring and the central pyridine ring is 46.3 (1)°. The molecular structure is stabilized by an intramolecular O—H...O hydrogen bonding, forming anS(6) ring motif. In the crystal, molecules are linkedviapairs of N—H...N hydrogen bonds, forming inversion di

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46

Brewster, James T., Harrison D. Root, Daniel Mangel, et al. "UO22+-mediated ring contraction of pyrihexaphyrin: synthesis of a contracted expanded porphyrin-uranyl complex." Chemical Science 10, no. 21 (2019): 5596–602. http://dx.doi.org/10.1039/c9sc01593k.

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47

Perrin, Monique, Alain Thozet, Pilar Cabildo, Rosa Ma Claramunt, Eduard Valenti, and José Elguero. "Molecular structure and tautomerism of 3,5-bis(4-methylpyrazol-1-yl)-4-methylpyrazole." Canadian Journal of Chemistry 71, no. 9 (1993): 1443–49. http://dx.doi.org/10.1139/v93-186.

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The title compound C12N6H14, 1, crystallizes in the space group P21/n (a = 8.222(2) Å, b = 27.336(8) Å, c = 5.574(2) Å, α = 90.00°, β = 100.97(4)°, γ = 90.00°), Z = 4, d = 1.308 g cm−3. The conformation about the N—C bonds linking the pyrazole rings can be defined as EZ, with "pyridine-like" nitrogen atoms in an anti disposition [Formula: see text] and "pyridine-like" and "pyrrole-like" nitrogen atoms in a syn disposition [Formula: see text] with regard to the central pyrazole. Intermolecular hydrogen bonds between the central and the terminal pyrazole ring of configuration Z form centrosymmet

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48

Ogurtsov, V. A., Yu V. Karpychev, and O. A. Rakitin. "Synthesis of 1-[(1,2-dithiol-3-ylidene)methyl]pyrrolo[1,2-a]pyrazines and 2-[(1,2-dithiol-3-ylidene)methyl]pyridines from 1,2-dithiole-3-thiones." Russian Chemical Bulletin 62, no. 4 (2013): 1076–79. http://dx.doi.org/10.1007/s11172-013-0144-8.

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49

Quo, Qi, Liangru Yang, Pu Mao, Yongmei Xiao, and Jinwei Yuan. "Crystal structure of 3-mesityl-1-[(pyridin-2-yl)methyl]-3,4,5,6-tetrahydropyrimidin-1-ium bromide monohydrate." Acta Crystallographica Section E Crystallographic Communications 71, no. 4 (2015): o224. http://dx.doi.org/10.1107/s2056989015003989.

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In the title hydrated salt, C19H24N3+·Br−·H2O, the values of the N—C bond lengths within the tetrahydropyrimidinium ring indicate delocalization of the N=C double bond. In the cation, the dihedral angle formed by the pyridine and benzene rings is 14.97 (12)°. In the crystal, ions and water molecules are linked by O—H...Br, O—H...N, C—H...Br and C—H...O hydrogen bonds into chains running parallel to thebaxis.

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50

Meyer, Andreas, Jennifer Wiecek, Gregor Schnakenburg, and Olav Schiemann. "The crystal structure of 4′-{4-[(2,2,5,5-tetramethyl-N-oxyl-3-pyrrolin-3-yl)ethynyl]phenyl}-2,2′:6′,2′′-terpyridine." Acta Crystallographica Section E Crystallographic Communications 71, no. 7 (2015): 870–74. http://dx.doi.org/10.1107/s2056989015012086.

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The terpyridine group of the title compound, C31H27N4O, assumes an all-transoidconformation and is essentially planar with the dihedral angles between the mean planes of the central pyridine and the two outer rings amounting to 3.87 (5) and 1.98 (5)°. The pyrroline-N-oxyl group commonly seen in such nitroxyls is found in the title structure and the mean plane of the pyrroline ring subtends a dihedral angle of 88.44 (7)° to the mean plane of the central pyridine ring. The intramolecular separation between the nitrogen atom of the central pyridine unit of the terpyridine group and the nitroxyl g

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