Hydroxyl-containing bis(sulfonates). Reaction of 1,4-dibromo-2,3-butanedione with water, methanol and sodium sulfite

2021 ◽  
pp. 1-12
Author(s):  
Gerasimos M. Tsivgoulis ◽  
Dimitris G. Vachliotis ◽  
Golfo G. Kordopati ◽  
Panayiotis V. Ioannou
Keyword(s):  
13C Nmr ◽  
Sodium Sulfite ◽  
The Other ◽  
Carbonyl Carbon ◽  
1H And 13C Nmr ◽  
Sodium Sulfonate ◽  
Pure Product ◽  
Methylene Groups ◽  
New Type ◽  
High Yields

Sulfonates are well-known substances with a variety of applications, e.g. as surfactants. On the other hand, bis(sulfonates) bearing hydroxyl or keto group(s) in between the sulfonate groups can be used with or without further modification as starting materials for the preparation of new type of molecules capable to form either complexes or in general supramolecular structures. The synthesis of three hydroxyl-bearing bis(sulfonates), 2-hydroxypropane-1,3-bis(sodium sulfonate) 4, DL-2,3-dihydroxybutane-1,4-bis(sodium sulfonate) 8, and sodium 2,3,4-trihydroxy-1-sulfonate 7 (as by-product) via the Strecker sulfonation are described. Interestingly, under similar conditions, sulfonation of 1,4-dibromo-2,3-butanedione 9 was found to be very complicated and no pure product could be isolated, despite previously reported results on sulfonation of α-halogenated ketones in high yields. There are indications that SO3 2 -  attacks at the carbonyl carbon of 9 followed by rearrangement and expulsion of SO4 2 - . 1,4-dibromo-2,3-butanedione 9, bearing two keto groups next to methylene groups, can potentially exist as enols or in the case of its solution in hydroxylic solvents in the form of hemiketals or geminal diols. This behavior of 9 when is dissolved in CDCl3, CD3OD and D2O was studied by means of UV-Vis, 1H and 13C NMR and the nature of the adducts formed was elucidated.

scholarly journals Dihydroisocoumarins and Dihydroisoflavones from the Rhizomes of Dioscorea collettii with Cytotoxic Activity and Structural Revision of 2,2′-Oxybis(1,4-di-tert-butylbenzene)

Molecules ◽  
2021 ◽  
Vol 26 (17) ◽  
pp. 5381
Author(s):  
Songsong Jing ◽  
Zhuo Qu ◽  
Chengcheng Zhao ◽  
Xia Li ◽  
Long Guo ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
13C Nmr ◽  
The Other ◽  
Cytotoxic Activities ◽  
Spectroscopic Methods ◽  
1H And 13C Nmr ◽  
Structural Revision ◽  
Nmr Data ◽  
H460 Cell ◽  
First Time

The investigation of the constituents of the rhizomes of Dioscorea collettii afforded one new dihydroisocoumarin, named (−)-montroumarin (1a), along with five known compounds—montroumarin (1b), 1,1′-oxybis(2,4-di-tert-butylbenzene) (2), (3R)-3′-O-methylviolanone (3a), (3S)-3′-O-methylviolanone (3b), and (RS)-sativanone (4). Their structures were elucidated using extensive spectroscopic methods. To the best of our knowledge, compound 1a is a new enantiomer of compound 1b. The NMR data of compound 2 had been reported but its structure was erroneous. The structure of compound 2 was revised on the basis of a reinterpretation of its NMR data (1D and 2D) and the assignment of the 1H and 13C NMR data was given rightly for the first time. Compounds 3a–4, three dihydroisoflavones, were reported from the Dioscoreaceae family for the first time. The cytotoxic activities of all the compounds were tested against the NCI-H460 cell line. Two dihydroisocoumarins, compounds 1a and 1b, displayed moderate cytotoxic activities, while the other compounds showed no cytotoxicity.

Preparation, 1H and 13C NMR Spectra of Substituted 2-Benzoylaminocarboxamides

1995 ◽  
Vol 60 (1) ◽  
pp. 150-160 ◽  
Author(s):  
Miloš Sedlák ◽  
Aleš Halama ◽  
Jaromír Kaválek ◽  
Vladimír Macháček ◽  
Vojeslav Štěrba
Keyword(s):  
13C Nmr ◽  
Ames Test ◽  
Nmr Spectra ◽  
Biologically Active Substances ◽  
Biologically Active ◽  
13C Nmr Spectra ◽  
1H And 13C Nmr ◽  
New Type ◽  
Active Substances ◽  
American Cyanamid Company

A new type of herbicides based on imidazolinones has been introduced into agriculture under commercial names of Arsenal, Pursuit, Scepter, Assert etc. by American Cyanamid Company since 1983. These compounds destroy diocotyledonous weeds and are almost nontoxic for mammals and fish (LD50 rat - 500 mg/kg, LD50 trout - 300 mg/kg) and nonmutagenic according to the AMES test. The aim of the present work is to synthesize substituted 2-benzoylaminocarboxamides as starting materials for preparation of imidazolinones and potential biologically active substances (Formulae I - III).

scholarly journals Cyclic Methacrylate Tetrahydropyrimidinones: Synthesis, Properties, (Co)Polymerization

Polymers ◽  
2021 ◽  
Vol 14 (1) ◽  
pp. 107
Author(s):  
Victor A. Gerasin ◽  
Marina V. Zhurina ◽  
Natalia A. Kleshcheva ◽  
Nikolai A. Sivov ◽  
Dmitry I. Mendeleev
Keyword(s):  
Radical Polymerization ◽  
13C Nmr ◽  
Salt Form ◽  
1H And 13C Nmr ◽  
Synthesis Conditions ◽  
Diallyldimethylammonium Chloride ◽  
Synthesis Properties ◽  
High Yields

During radical polymerization of novel biocidal methacrylate guanidine monomers, a cyclic byproduct was discovered and identified as 2-imino-5-methyltetrahydropyrimidin-4(1H)-one (THP). Its methacrylate salt (MTHP) was synthesized and characterized via 1H and 13C NMR and pyrolysis chromatography. Synthesis conditions of both THP and MTHP were optimized to high yields, and both MTHP homopolymerization (in aqua) and copolymerization with diallyldimethylammonium chloride (in aqua in salt form) were successfully carried out with middle to high yields, providing a promising platform for potential tailored biocide polymers.

scholarly journals Synthesis of some biologically active 2,4'-bipyridine-5-carbonitriles carrying the 4-hydroxyphenylthio moiety

2009 ◽  
Vol 74 (7) ◽  
pp. 733-743 ◽  
Author(s):  
T. Karabasanagouda ◽  
Vasudeva Adhikari ◽  
G. Parameshwarappa
Keyword(s):  
13C Nmr ◽  
Ammonium Acetate ◽  
Ethyl Cyanoacetate ◽  
Aromatic Aldehydes ◽  
Biologically Active ◽  
The Other ◽  
Mass Spectral Data ◽  
1H And 13C Nmr ◽  
Mass Spectral

A series of new 4-aryl-2'-[(4-hydroxyphenyl)thio]-6oxo-1,6-dihydro- 2,4'-bipyridine-5-carbonitriles (3a-k) and 6-amino-4aryl-2'-[(4-hydroxyphenyl) thio]-2,4'-bipyridine-5-carbonitriles (4a-h) were synthesized from 4-hydroxythiophenol (1). The reaction of 4-hydroxythiophenol with 4-acetyl-2-chloropyridine yielded 1-{2-[(4-hydroxyphenyl)thio]pyridin-4-yl}ethanone (2). Further treatment of 2 with ethyl cyanoacetate in the presence of ammonium acetate with various aromatic aldehydes furnished the compounds 3a-k. On the other hand, condensation of 2 with aromatic aldehydes in the presence of alcoholic malononitrile in ammonium acetate gave compounds 4a-h. The structures of the newly synthesized compounds were established on the basis of their elemental analysis, as well as their IR, 1H- and 13C-NMR and mass spectral data. All the title compounds were subjected to in vitro antibacterial testing against two strains and antifungal screening against two fungi. Some of the compounds showed promising activity.

A 13C NMR Study on the Adsorption Characteristics of HEMA to Dentinal Collagen

2002 ◽  
Vol 81 (7) ◽  
pp. 469-471 ◽  
Author(s):  
N. Nishiyama ◽  
K. Suzuki ◽  
K. Komatsu ◽  
S. Yasuda ◽  
K. Nemoto
Keyword(s):  
Hydrogen Bond ◽  
13C Nmr ◽  
The Other ◽  
Carbonyl Carbon ◽  
Adhesive Resin ◽  
Adsorption Characteristics ◽  
Ester Carbonyl ◽  
Nmr Study ◽  
Insight Into ◽  
C Nmr

To develop a more effective primer, we must understand how 2-hydroxyethylmethacrylate, the HEMA primer, enhances bonding at the resin-dentin interface. In this study, to obtain an insight into the adhesion mechanisms of adhesive resin to etched dentin through HEMA, we examined the adsorption characteristics of HEMA to dentinal collagen by using the 13C NMR technique. The addition of dentinal collagen to the HEMA solution resulted in a decrease in T1 values of carbons attributed to the HEMA, thus reflecting an interaction between HEMA and collagen. Specifically, a reduction in the T1 value in the ester carbonyl carbon attributed to HEMA greater than that in the other carbons suggested the formation of a hydrogen bond between the ester carbonyl group in HEMA and the dentinal collagen.

scholarly journals Assignment of 1H and 13C NMR spectral data of diastereomeric acetals directly from their mixture by spectral simulation

2021 ◽  
Vol 19 (2) ◽  
pp. 69-79
Author(s):  
Milan Nesic ◽  
Niko Radulovic
Keyword(s):  
Spectral Data ◽  
13C Nmr ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
Coupling Constants ◽  
Racemic Mixture ◽  
13C Nmr Spectra ◽  
Spectral Simulation ◽  
1H And 13C Nmr ◽  
Methylene Groups

Herein, an NMR spectral analysis was performed of a mixture of diastereomeric acetals synthesized from 2-fluorobenzaldehyde and a racemic mixture of 4-methylpentan-2-ol. The simulated 1H- and 13C-NMR spectra of individual diastereomers, as well as their superimposed and summed spectra, were compared with the obtained experimental spectra. Spin simulation of proton signals was particularly useful for the assignment of the aromatic part of the molecules and of the diastereotopic protons of the methylene groups. The isomer NMR spectral data - chemical shifts, coupling constants, HMBC and NOESY interactions were systematized in appropriate tables and schemes.

Some Considerations Regarding the 1H and 13C Spectra of 4-(1-azulenyl)-2,6-bis(2-heteroaryl-vinyl)- pyrylium and Pyridinium and their Corresponding Pyridines

2018 ◽  
Vol 69 (1) ◽  
pp. 64-69
Author(s):  
Liviu Birzan ◽  
Mihaela Cristea ◽  
Constantin C. Draghici ◽  
Alexandru C. Razus
Keyword(s):  
Double Bond ◽  
13C Nmr ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
Pyridinium Salts ◽  
13C Nmr Spectra ◽  
1H And 13C Nmr ◽  
Pyrylium Salts

The 1H and 13C NMR spectra of several 2,6-diheteroarylvinyl heterocycles containing 4-azulenyl moiety were recorded and their proton and carbon chemical shifts were compared with those of the compounds without double bond between the heterocycles. The influence of the nature of central and side heterocycles, molecule polarization and anisotropic effects were revealed. The highest chemical shifts were recorded for the pyrylium salts and the lowest at pyridines, but in the case of the pyridinium salts, the protons chemical shifts at the central heterocycle are more shielded due to a peculiar anisotropy of the attached vinyl groups.

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.

Synthesis of Highly Functionalized Quinazoline-2,4(1H,3H)-diones from Isocyanides, Aniline and Isocyanate via Cu-Catalyzed Intermolecular C-H Activation Reactions

2020 ◽  
Vol 17 (11) ◽  
pp. 832-836
Author(s):  
Manijeh Nematpour ◽  
Hossein Fasihi Dastjerdi ◽  
Mehdi Jahani ◽  
Sayyed Abbas Tabatabai
Keyword(s):  
13C Nmr ◽  
Reaction Times ◽  
High Yield ◽  
One Pot ◽  
1H And 13C Nmr ◽  
Activation Reaction ◽  
Elemental Analyses

A simple and appropriate procedure for the synthesis of quinazoline-2,4(1H,3H)-dione derivatives from isocyanides, aniline and isocyanate via the Cu-catalyzed intramolecular C-H activation reaction is reported. The advantages of this method are one-pot conditions, accessible starting materials- catalyst, high yield of products, and short reaction times. The structures are confirmed spectroscopically (1H- and 13C-NMR, IR and EI-MS) and by elemental analyses.

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