scholarly journals Synthesis and X-ray diffraction of derivatives 2,4-dimethyl-6-oxo-1,6-dihydropyridin-3-carboxamide

2019 ◽  
Vol 60 (10) ◽  
pp. 1-23
Author(s):  
Ekaterina M. Feklicheva (Okul) ◽  
◽  
Victor B. Rybakov ◽  
Evgeny V. Babaev ◽  
Evgeny N. Ofitserov ◽  
...  
Keyword(s):  
Nmr Spectra ◽  
Synthesis Methods ◽  
X Ray Diffraction ◽  
Single Crystal Diffraction ◽  
Torsion Angles ◽  
X Ray ◽  
Nitrogenous Base ◽  
Derivatives Of ◽  
By Products ◽  
Chloride Monohydrate

Based on the synthesized starting 2,4-dimethyl-6-oxo-1,6-dihydropyridin-3-carboxamide crystallizing as a dihydrate, 9 derivatives of it including O- and N-phenacyl substituted products were obtained through original rearrangements and cyclizations. The corresponding oxazolopyridinium perchlorate was obtained from the latter preparation in the presence of acid, from which indolysin was obtained under the action of a nitrogenous base. The obtained molecular and crystal structures of all the compounds were studied by single crystal diffraction: 2,4-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxamide dihydrate, 6-hydroxy-2,4-dimethyl-3-carbamoyl-pyridinium chloride monohydrate, 2,4-dimethyl-6-methoxypyridine-3-carboxamide, 1-[2-(4-methylphenyl)-2-oxoethyl]-2,4-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxamide, 2,4-dimethyl-6-oxo-1-[2- (4-[chlorophenyl)-2-oxoethyl]-1,6-dihydropyridine-3-carboxamide, 2,4-dimethyl-6-[2-(4-methylphenyl)-2-oxo-ethoxy]pyridin-3-carbox-amide, 2,4-dimethyl-6-[2-(4-chlorophenyl)-2-oxoethoxy] pyridin-3-carb xamide, 6-carbamoyl-2-(4-chlorophenyl)-5,7-dimethyl[1,3]oxazolo[3,2-a]pyridin-4 perchlorate, 7-methyl-5-morpholin-4 -yl-2-(4-chlorophenyl) indolysin-8-carboxamide. A structural analysis of the by-products of 1,4-bis (4-methylphenyl) butane-1,4-dione and 1,4-bis(4-chlorophenyl) butane-1,4-dione was also carried out. The synthesis methods of each of them are given. A comparative analysis of bond lengths, valence and torsion angles in similar fragments of molecules is carried out. Hydrogen bonds were revealed in the structures and their influence on the strength of molecular packing in crystals was shown. All structures of the studied compounds, in addition to XRD, are characterized by 1H NMR spectra.

Photoreaktionen von Dekacarbonyldirhenium mit Allen und unverzweigten Allenderivaten / Photoreactions of Decacarbonyldirhenium with Allene and Unbranched Derivatives of Allene

1995 ◽  
Vol 50 (4) ◽  
pp. 649-660 ◽  
Author(s):  
Cornelius G. Kreiter ◽  
Wolfgang Michels ◽  
Gerhard Heeb
Keyword(s):  
Nmr Spectra ◽  
Crystal And Molecular Structure ◽  
Reaction Products ◽  
X Ray Diffraction ◽  
X Ray ◽  
H Nmr ◽  
Oxidative Rearrangement ◽  
Dirhenium Complexes ◽  
Derivatives Of ◽  
By Products

Decacarbonyldirhenium (1) reacts upon UV irradiation with allene (2), 1,2-butadiene (3) and 2,3-pentadiene (4) preferentially by CO substitution and oxidative rearrangement to the corresponding enneacarbonyl-μ-η1:3-endiyl-dirhenium complexes 5, 9, and 15 and to the octacarbonyl-μ-η2:2-allene-dirhenium complexes 6, the stereoisomers 10, 11, and 16. At elevated temperature 5, 9, and 15 loose CO and yield by a reductive rearrangement also the complexes 6, 10, 11, and 16. In addition to these main products, depending upon the allene derivative used, various by-products are obtained.By-products of the reaction o f 1 with 2 are octacarbonyl-μ-η3:3-(2,3-dimethylene-buta-1,4- diyl)dirhenium (7) and μ-η2:2-allene-hexacarbonyl-μ-η1:3-1-propene-1,3-diyl-dirheniurn (8). The photo reaction of 1 with 3 yields, in addition to 9-11, tetracarbonyl-η3-(E-5-ethylidene- 4-methyl-2-cyclopenten-1-yl)rhenium (12) and tetracarbonyl-η3-(Z-5-ethyliden-4- methyl-2-cyclopenten-1-yl)rhenium (13) as a mixture of isomers. 1 and 4 form the by-products tetracarbonyl-η3-(EZ-3-penten-2-yl)rhenium (17), tetracarbonyl-η3-(EE-3-penten-2-yl)rhenium (18) and heptacarbonyl-μ-η1:2:1:2-(4,5-dimethyl-2,6-octadiene-3,6-diyl)dirhenium (19) with an unusually bridging and chelating ligand. The constitutions of the reaction products have been concluded from the IR and 1H NMR spectra. For 19 the crystal and molecular structure has been determined by X-ray diffraction analysis.

Darstellung, 11B-, 13C-NMR- und Schwingungsspektren von Cs2[B6H5(p-C6H4(NO2))] und Cs2[B6H5(C6H3-l-(CH3)-5-(NO2))] sowie Kristallstruktur von (CH2Py2)[B6Cl5(p-C6H4(NO2))]·CH3CN / Preparation, 11B , 13C-NMR and Vibrational Spectra of Cs2[B6H5(p-C6H4(NO2))], Cs2[B6H5 (C6H3-1 -(CH3 )-5-(NO2))] and Crystal Structure of (CH2Py2)[B6Cl5(p-C6H4(NO2))]·CH3CN

2000 ◽  
Vol 55 (11) ◽  
pp. 1031-1036
Author(s):  
S. Zander ◽  
W. Preetz
Keyword(s):  
13C Nmr ◽  
Nmr Spectra ◽  
Deae Cellulose ◽  
Ion Exchange Chromatography ◽  
Exchange Chromatography ◽  
X Ray Diffraction ◽  
Orthorhombic Space Group ◽  
X Ray ◽  
Derivatives Of ◽  
Ir And Raman

The first aryl derivatives of c/oso-hexahydrohexaborate are formed by reaction of [B6H6]2- with 1-bromo-4-nitrobenzene and 2-bromo-5-nitrotoluene in acetonitrile at 80 °C. Cs2[B6H5- (1,4-C6H4(NO2))] and Cs2[B6H5(C6H3-1-(CH3)-5-(NO2))] can be isolated by ion exchange chromatography on diethylaminoethyl (DEAE) cellulose. Further treatment with /V-chlorosuccinimide yields the perhalogenated derivative (CH2Py2)[B6Cl5(1,4-Ph(NO2))]CH3CN which has been characterized by X-ray diffraction analysis (orthorhombic, space group P2( 2,2t, a = 9.810(4), b - 14.412(3), c - 18.586(9) A, Z = 4). The 11B NMR spectra of all compounds are consistent with a monosubstituted B6-cluster. The IR and Raman spectra exhibit characteristic BB, BH, CH, CC and NO vibrations, respectively.

Syntheses and crystal structures of new aurate salts of adenine or guanine nucleobases

2020 ◽  
Vol 76 (2) ◽  
pp. 139-147
Author(s):  
Anton Savchenkov ◽  
Ludmila Demina ◽  
Alexey Safonov ◽  
Mikhail Grigoriev ◽  
Roman Solovov ◽  
...  
Keyword(s):  
Crystal Structures ◽  
Noncovalent Interactions ◽  
Spectroscopic Techniques ◽  
Stacking Interactions ◽  
X Ray Diffraction ◽  
X Ray ◽  
Ft Ir ◽  
Nitrogenous Base ◽  
Ir Spectroscopic ◽  
Chloride Monohydrate

Two new gold(III) complexes with adenine or guanine nitrogenous bases as counter-cations were synthesized. These are 6-amino-7H-purine-1,9-diium tetrachloridogold(III) chloride monohydrate, (C5H7N5)[AuCl4]Cl·H2O, 1, and 2-amino-6-oxo-6,7-dihydro-1H-purin-9-ium tetrachloridogold(III) hemihydrate, (C5H6N5O)[AuCl4]·0.5H2O, 2. Their crystal structures were studied using single-crystal X-ray diffraction and FT–IR spectroscopic techniques. The arrangement of species in the studied crystal structures implies π-stacking interactions, as well as concomitant C—H...π interactions, hydrogen bonds and other types of noncovalent interactions, which were studied qualitatively and quantitatively using the method of molecular Voronoi–Dirichlet polyhedra. The variation of the nitrogenous base from adenine to guanine results in evident differences in the packing of the species in the crystals of 1 and 2. The splitting and shifting of bands in the FT–IR spectra of the title compounds reveals several features representative of noncovalent interactions in their crystal structures.

The Electron Effect of Aromatic Group: Control Conformation of 2-Aromatic Cyclododecanone Derivatives

2020 ◽  
Vol 24 (10) ◽  
pp. 1139-1147
Author(s):  
Yang Mingyan ◽  
Wang Daoquan ◽  
Wang Mingan
Keyword(s):  
1H Nmr ◽  
13C Nmr ◽  
Nmr Spectra ◽  
Coupling Constants ◽  
The Other ◽  
Repulsive Interaction ◽  
X Ray Diffraction ◽  
X Ray ◽  
Electron Effect ◽  
Group Control

2-Phenylcyclododecanone and 2-cyclohexylcyclododecanone derivatives were synthesized and characterized by 1H NMR, 13C NMR, HR-ESI-MS and X-ray diffraction. Their preferred conformations were analyzed by the coupling constants in the 1H NMR spectra and X-ray diffraction, which showed the skeleton ring of these derivatives containing [3333]-2-one conformation, and the phenyl groups were located at the side-exo position of [3333]-2-one conformation due to the strong π-π repulsive interaction between the π- electron of benzene ring and π-electron of carbonyl group. The cyclohexyl groups were located at the corner-syn or the side-exo position of [3333]-2-one conformation depending on the hindrance of the other substituted groups. The π-π electron effect played a crucial role in efficiently controlling the preferred conformation of 2-aromatic cyclododecanone and the other 2-aromatic macrocyclic derivatives with the similar preferred square and rectangular conformations.

Preparation, properties and structure of some intermediate nido- and arachno-monocarbaboranes

1981 ◽  
Vol 46 (10) ◽  
pp. 2345-2353 ◽  
Author(s):  
Karel Baše ◽  
Bohumil Štíbr ◽  
Jiří Dolanský ◽  
Josef Duben
Keyword(s):  
Transition Metal ◽  
Metal Complexes ◽  
Transition Metal Complexes ◽  
Nmr Spectra ◽  
Liquid Ammonia ◽  
X Ray Diffraction ◽  
X Ray ◽  
H Nmr ◽  
Starting Compound

The 6-N(CH3)3-6-CB9H11 carbaborane reacts with sodium in liquid ammonia with the formation of 6-CB9H12- which was used as a starting compound for preparing the 4-CB8H14, 9-L-6-CB9H13 (L = (CH3)2S, CH3CN and P(C6H5)3), 1-(η5-C5H5)-1,2-FeCB9H10-, and 2,3-(η5-C5H5)2-2,31-Co2CB9H10- carboranes. The 4-CB8H14 compound was dehydrogenated at 623 K to give 4-(7)-CB8H12 carborane. Base degradation of 6-N(CH3)3-6-CB9H11 in methanol resulted in the formation of 3,4-μ-N(CH3)3CH-B5H10. The structure of all compounds was proposed on the basis of their 11B and 1H NMR spectra and X-ray diffraction was used in the case of the transition metal complexes.

Axially Chiral Bis(α-amino Acid)s and Their Deamino Analogues. Synthesis and Configurational Assignment

1998 ◽  
Vol 63 (2) ◽  
pp. 211-221 ◽  
Author(s):  
Miloš Tichý ◽  
Luděk Ridvan ◽  
Miloš Buděšínský ◽  
Jiří Závada ◽  
Jaroslav Podlaha ◽  
...  
Keyword(s):  
Amino Acid ◽  
Nmr Spectra ◽  
Building Blocks ◽  
X Ray Diffraction ◽  
Amino Groups ◽  
X Ray ◽  
Configurational Assignment ◽  
Symmetry Properties ◽  
Axially Chiral ◽  
Polymeric Structures

The axially chiral bis(α-amino acid)s cis-2 and trans-2 as possible building blocks for polymeric structures of novel type of helicity were prepared. Their configuration has been determined by NMR spectroscopy and, in the case of the trans-isomer, confirmed by single-crystal X-ray diffraction. Analogous pair of stereoisomeric diacids cis-3 and trans-3, devoid of the amino groups, was also prepared and their configuration assigned. The observed differences in the NMR spectra of cis- and trans-isomers of 2 and 3 are discussed from the viewpoint of their different symmetry properties.

Unusual Rearrangement of Naphthalene in the Synthesis of a Novel B8-B8-Bridged Derivative in the [(1,2-C2B9H11)2-3-Co]- Series. X-Ray Structure and 11B NMR Spectra of [8,8'-μ-(CH2-C9H6)-(1,2-C2B9H10)2-3-Co]- (CH3)4N+

1997 ◽  
Vol 62 (5) ◽  
pp. 746-751 ◽  
Author(s):  
Andreas Franken ◽  
Jaromír Plešek ◽  
Christiane Nachtigal
Keyword(s):  
Nmr Spectroscopy ◽  
Single Crystal ◽  
Nucleophilic Substitution ◽  
Nmr Spectra ◽  
X Ray Diffraction ◽  
X Ray ◽  
Unusual Rearrangement ◽  
Multinuclear Nmr Spectroscopy ◽  
11B Nmr ◽  
Isolated Compound

On treatment of the [(1,2-C2B9H11)2Co]- ion with naphthalene in presence of AlCl3 a remarkably bridged [8,8'-μ-(CH2-C9H6)-(1,2-C2B9H10)2-3-Co]- ion is obtained as a single isolated compound. The triatomic -CH2-C9H6- bridge is derived from the rearranged naphthalene nucleus. The mechanism of this reaction is obscure but it does resemble the "Electrophile-Induced Nucleophilic Substitution" reported earlier. The structure of the compound was established by multinuclear NMR spectroscopy and by single crystal X-ray diffraction.

Crystal Forms of Semisynthetic Ergot Alkaloid Terguride

2002 ◽  
Vol 67 (4) ◽  
pp. 479-489 ◽  
Author(s):  
Michal Hušák ◽  
Bohumil Kratochvíl ◽  
Ivana Císařová ◽  
Ladislav Cvak ◽  
Alexandr Jegorov ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Ergot Alkaloid ◽  
Simplified Model ◽  
Quantum Mechanical ◽  
Quantum Mechanical Calculations ◽  
X Ray Diffraction ◽  
Torsion Angles ◽  
Crystal Forms ◽  
X Ray ◽  
Independent Molecules

Two new structures of semisynthetic ergot alkaloid terguride created by unusual number of symmetry-independent molecules were determined by X-ray diffraction methods at 150 K. Form A (monoclinic, P212121, Z = 12) contains three symmetry-independent terguride molecules and two molecules of water in the asymmetric part of the unit cell. The form CA (monoclinic, P21, Z = 8) is an anhydrate remarkable by the presence of four symmetry-independent molecules in the crystal structure. Conformations of twelve symmetry-independent molecules that were found in four already described terguride structures are compared with torsion angles obtained by ab initio quantum-mechanical calculations for the simplified model of N-cyclohexyl-N'-diethylurea.

Synthesis of Galactomannan Sulfate-Citrate

2022 ◽  
Vol 1049 ◽  
pp. 218-223
Author(s):  
Aleksandr S. Kazachenko ◽  
Yuriy N. Malyar ◽  
Anna S. Kazachenko
Keyword(s):  
Biological Activity ◽  
Ftir Spectroscopy ◽  
X Ray Diffraction ◽  
Absorption Bands ◽  
X Ray ◽  
Mixed Ester ◽  
First Time ◽  
Derivatives Of

Sulfated derivatives of polysaccharides have anticoagulant, hypolipedimic and other biological activity. In this work, a complex mixed ester of galactomannan, its sulfate-citrate, was obtained for the first time. The introduction of citrate and sulfate groups was proved by FTIR spectroscopy by the appearance of corresponding absorption bands. It was shown by X-ray diffraction that the introduction of the citrate group leads to the amorphization of the galactomannan structure.

Sign in / Sign up

Export Citation Format

Share Document