scholarly journals Synthesis and Characterization of a Butenafine Analogue

2018 ◽  
pp. 1-11
Author(s):  
M. A. Muhammad ◽  
A. M. Jimoh ◽  
A. Awwal
Keyword(s):  
1H Nmr ◽  
13C Nmr ◽  
Reductive Amination ◽  
Reducing Agent ◽  
Target Compound ◽  
Nmr Spectrum ◽  
Tertiary Butyl ◽  
Tert Butyl ◽  
Chloride Catalyst ◽  
Solvent Action

Aims: The study aims: (I) To synthesise N-(4-(tert-butyl) benzyl)-1-(4-tert-butyl) phenyl)-N-methyl methanaminium chloride, an  analogue  of butenafine from tertiary-butyl benzyl derivatives, (II) to compare the solvent actions of Tetrahydrofuran (THF), acetonitrile, methanol and 1,2-dichloroethane (DCE), and the reducing efficiencies of NaBH4 and sodium triacetoxyborohydride (STAB) during the synthesis. Study Design:  The study involved laboratory experiments leading to the synthesis of the target compound by varying the non-aqueous solvents used, the reducing agent and the temperature of the operations. Silica chloride catalyst was used to speed up the reaction in one of the syntheses and in each synthesis, Thin Layer Chromatography was used to monitor the progress of the reaction. The time taken by each reaction and the yield were used as the basis for determining the solvent action and the reducing efficiency.  Place and Duration of Study: M.Sc. Access controlled Teaching Laboratory, School of Chemistry, Newcastle University, New castle upon Tyne, United Kingdom from June to August 2012. Methodology: Reductive amination was carried out by reacting 4-tert-butylbenzaldehyde and 4-tert-butylbenzylamine, using the direct and then the indirect approaches. This was followed by methylation using the Eschweiler-Clarke reaction in each of the two approaches. The time taken by each reaction was monitored and the product of each approach was characterised by EIS-MS, 1H NMR, 13C NMR and FTIR. Results: 1,2-dichloroethane gave the best solvent action at 40°C (Yield: 75%) and NaBH4  gave the best-reducing action with silica chloride catalyst at 25°C (Yield: 50%). At the end of each synthesis,  in all obtained  products, 1H NMR spectrum gave a single peak of 18 hydrogen atoms at 1.3 -1.5 ppm for the existence of 6 methyl groups in the two tertiary-butyl substituents, the 13C NMR spectrum also showed a peak at  31-32 ppm for the six methyl carbon atoms in the two tertiary-butyl substituents, the FTIR spectrum showed  a strong band at  2460 cm-1 for the presence of a tertiary ammonium ion and finally the EIS-MS gave  a mass to charge ratio of 324.2693 as a confirmation of the relative molecular mass of the compound. Conclusion:  The target compound can be synthesised by both direct and the indirect approaches of reductive amination in any of the solvents tested with/without a catalyst at room or elevated temperature using NaBH4 or STAB as a reducing agent but the best solvent action can be achieved with DCE at 40°C and the best-reducing action can be achieved with NaBH4 in the presence of silica chloride.

scholarly journals 6-[1-Acetyl-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-3-yl]-2(3H)-benzoxazolone

Molbank ◽  
10.3390/m1021 ◽  
2018 ◽  
Vol 2018 (4) ◽  
pp. M1021
Author(s):  
Yordanka Ivanova ◽  
Antonya Todorova ◽  
Christo Chanev ◽  
Ognyan Petrov
Keyword(s):  
Acetic Acid ◽  
Hydrazine Hydrate ◽  
1H Nmr ◽  
Elemental Analysis ◽  
13C Nmr ◽  
Title Compound ◽  
Target Compound

The title compound, 6-[1-acetyl-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl]-2(3H)-benzoxazolone, was synthesized by condensation of 6-[3-(4-methoxyphenyl)-2-propenoyl]-2(3H)-benzoxazolone (1) and hydrazine hydrate in acetic acid in 84% yield. The structure of the target compound was confirmed using 1H-NMR, 13C-NMR, IR, MS, and elemental analysis.

scholarly journals One-Dimensional 13C NMR Is a Simple and Highly Quantitative Method for Enantiodiscrimination

Molecules ◽  
2018 ◽  
Vol 23 (7) ◽  
pp. 1785 ◽  
Author(s):  
Peter Lankhorst ◽  
Jozef van Rijn ◽  
Alexander Duchateau
Keyword(s):  
1H Nmr ◽  
13C Nmr ◽  
Quantitative Method ◽  
Enantiomeric Excess ◽  
Nmr Spectrum ◽  
One Dimensional ◽  
Nmr Method ◽  
Relative Standard ◽  
Excess Value ◽  
Chiral Solvating Agent

The discrimination of enantiomers of mandelonitrile by means of 1D 13C NMR and with the aid of the chiral solvating agent (S)-(+)-1-(9-anthryl)-2,2,2-trifluoroethanol (TFAE) is presented. 1H NMR fails for this specific compound because proton signals either overlap with the signals of the chiral solvating agent or do not show separation between the (S)-enantiomer and the (R)-enantiomer. The 13C NMR method is validated by preparing artificial mixtures of the (R)-enantiomer and the racemate, and it is shown that with only 4 mg of mandelonitrile a detection limit of the minor enantiomer of 0.5% is obtained, corresponding to an enantiomeric excess value of 99%. Furthermore, the method shows high linearity, and has a small relative standard deviation of only 0.3% for the minor enantiomer when the relative abundance of this enantiomer is 20%. Therefore, the 13C NMR method is highly suitable for quantitative enantiodiscrimination. It is discussed that 13C NMR is preferred over 1H NMR in many situations, not only in molecules with more than one chiral center, resulting in complex mixtures of many stereoisomers, but also in the case of molecules with overlapping multiplets in the 1H NMR spectrum, and in the case of molecules with many quaternary carbon atoms, and therefore less abundant protons.

ASSIGNMENT OF NMR SIGNALS FOR CHLOROPRENE RUBBER BY TWO-DIMENSIONAL NMR SPECTROSCOPY

2013 ◽  
Vol 86 (2) ◽  
pp. 250-260
Author(s):  
Takayuki Saito ◽  
Seiichi Kawahara ◽  
Yoshito Ohtake
Keyword(s):  
Nmr Spectroscopy ◽  
1H Nmr ◽  
13C Nmr ◽  
Quantum Correlation ◽  
Multiple Bond ◽  
Multiple Quantum ◽  
Heteronuclear Multiple Bond Correlation ◽  
Nmr Spectrum ◽  
Chloroprene Rubber ◽  
Nmr Signals

ABSTRACT Various pulse techniques of NMR spectroscopy were applied to CR to assign some small signals in 13C and 1H NMR spectra for the rubber. First, the rubber was subjected to distortionless enhancement by polarization transfer and attached proton test. The small signals in the 13C NMR spectrum were assigned to secondary, tertiary, and quaternary carbons. Second, correlations between 13C and 1H were investigated by heteronuclear multiple quantum correlation, heteronuclear two bond correlation, and heteronuclear multiple bond correlation measurements to assign the small signals in the 13C NMR spectrum in detail. By using the resulting correlations between 13C and 1H, the small unassigned signals in 1H NMR spectrum were assigned to methylene and methine protons of the rubber.

scholarly journals (S)-Ethyl 2-(tert-butoxycarbonylamino)-3-(2-iodo-4,5-methylenedioxyphenyl)propanoate

Molbank ◽  
10.3390/m1049 ◽  
2019 ◽  
Vol 2019 (1) ◽  
pp. M1049
Author(s):  
Giovanni Lentini ◽  
Maria Cavalluzzi ◽  
Leonardo Degennaro ◽  
Giuseppe Fracchiolla ◽  
Filippo Perna ◽  
...  
Keyword(s):  
Nmr Spectroscopy ◽  
1H Nmr ◽  
13C Nmr ◽  
Title Compound ◽  
Target Compound ◽  
Esi Ms

A multistep gram-scale synthesis of (S)-ethyl 2-(tert-butoxycarbonylamino)-3-(2-iodo-4,5-methylenedioxyphenyl)propanoate (2) has been developed. The title compound was prepared starting from commercially available l-DOPA which was O- and N-protected before undergoing iodination by CF3CO2Ag/I2. The structure of the target compound was confirmed using IR, 1H-NMR, 13C-NMR, 2D (COSY, HSQC) NMR spectroscopy, as well as ESI-MS and HRMS.

scholarly journals Synthesis and Characterisation of 1,1′-{[3,5-Bis(dodecyloxy-carbonyl)-4-(thiophen-3-yl)-1,4-dihydropyridine-2,6-diyl]bis-(methylene)}bis(pyridin-1-ium) Dibromide

Molbank ◽  
10.3390/m1311 ◽  
2021 ◽  
Vol 2022 (1) ◽  
pp. M1311
Author(s):  
Martins Rucins ◽  
Karlis Pajuste ◽  
Aiva Plotniece ◽  
Nadiia Pikun ◽  
Roman Rodik ◽  
...  
Keyword(s):  
Aqueous Solution ◽  
Nucleophilic Substitution ◽  
1H Nmr ◽  
13C Nmr ◽  
Target Compound ◽  
Two Component

In the present work, construction of double-charged cationic amphiphilic 1,1′-{[3,5-bis(dodecyl¬oxy-carbonyl)-4-(thiophen-3-yl)-1,4-dihydropyridine-2,6-diyl]bis-(methylene)}bis(pyridin-1-ium) dibromide (7) was performed in four steps. Dodecyl 3-oxobutanoate (1) was condensed with thiophene-3-carbaldehyde (2) which was necessary for Hantzsch cyclisation dodecyl (E/Z)-3-oxo-2-(thiophen-3-ylmethylene)butanoate (3). Two-component Hantzsch type cyclisation of dodecyl (E/Z)-3-aminobut-2-enoate (4) and dodecyl (E/Z)-3-oxo-2-(thiophen-3-ylmethylene)butanoate (3) gave 3,5-bis(dodecyloxycarbonyl)-2,6-dimethyl-4-(thiophen-3-yl)-1,4-dihydropyridine (5). Bromination of compound 5 followed by nucleophilic substitution of bromine with pyridine gave the desired cationic amphiphilic 1,4-dihydropyridine 7. The obtained target compound 7 and new intermediates 3, 5 and 6 were fully characterised by IR, UV, 1H NMR, 13C NMR, HRMS or microanalysis. Characterisation of nanoparticles formed by the cationic 1,4-dihydropyridine 7 in an aqueous solution was performed by DLS measurements.

scholarly journals N-(9,10-Dioxo-9,10-dihydroanthracen-1-yl)-2-methylbenzamide

Molbank ◽  
10.3390/m1175 ◽  
2020 ◽  
Vol 2020 (4) ◽  
pp. M1175
Author(s):  
Hamad H. Al Mamari ◽  
Ahmed Al Sheidi
Keyword(s):  
1H Nmr ◽  
13C Nmr ◽  
Title Compound ◽  
Short Note ◽  
Spectroscopic Methods ◽  
Target Compound ◽  
Bond Functionalization ◽  
Directing Group ◽  
Metal Catalyzed

In the present Short Note, we report a synthesis for the title compound, N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-2-methylbenzamide by reacting 2-methylbenzoyl chloride (or 2-methylbenzoic acid) with 1-aminoanthraquinone. The synthesized target compound was fully characterized by various spectroscopic methods (1H-NMR, 13C-NMR, IR, GC-MS). The importance of this compound lies its possession of an N,O-bidentate directing group, potentially suitable for metal-catalyzed C-H bond functionalization reactions.

scholarly journals Isolation of Khusimol from the Root of Vetiver (Vetiveria zizanioides L. Nash) Grown in Samarang – Garut and the Study of its Profile after Harvesting

2021 ◽  
Vol 11 (2) ◽  
pp. 3549-3559
Keyword(s):  
Essential Oil ◽  
1H Nmr ◽  
Column Chromatography ◽  
13C Nmr ◽  
Structure Elucidation ◽  
Molecular Formula ◽  
Harvest Time ◽  
Target Compound ◽  
Vetiveria Zizanioides ◽  
Nmr Data

Vetiver oil is a type of essential oil extracted from the vetiver plant's roots. Vetiver oil is commonly used as a major odor contributor in the fragrance and aromatherapy industry. This study aimed to isolation khusimol compound from vetiver oil, which will be used as a marker and determine khusimol content in various drying times after harvesting. The target compound was found in the combination of fraction 3 (GF-3). Furthermore, GF-3 was subfractionated by classical column chromatography. Structure elucidation of isolate X was performed by NMR. 1H-NMR and 13C-NMR data of isolate X as the same as 1H-NMR and 13C-NMR data of khusimol compound in literature. Molecular formula of khusimol C15H24O. Khusimol content in extract with various drying times after harvest time 0 hr, 6 hr, 12 hr, 24 hr, 36 hr and 48 hr were 1.95 ± 0.02; 2.15 ± 0.02; 2.30 ± 0.03; 2.81 ± 0.01; 1.72 ± 0.03 and 1.38 ± 0.02 mg/100 g. The odor contributor compound was khusimol (C15H24O). The highest khusimol content was revealed by vetiver extract, which drying for 24 hr after harvest. Drying vetiver more than 24 hr could reduce khusimol content.

Synthesis and Biological Evaluation of Various New Substituted 1,3,4-oxadiazole-2-thiols

2008 ◽  
Vol 59 (4) ◽  
Author(s):  
Gabriela Laura Almajan ◽  
Stefania Felicia Barbuceanu ◽  
Ioana Saramet ◽  
Mihaela Dinu ◽  
Cristian Vasile Doicin ◽  
...  
Keyword(s):  
Biological Activity ◽  
Plant Growth ◽  
1H Nmr ◽  
Elemental Analysis ◽  
13C Nmr ◽  
Biological Evaluation ◽  
Ethyl Chloroacetate ◽  
Low Concentrations ◽  
Synthesis And Biological Evaluation

5-[4-(4X-phenylsulfonyl)phenyl]-1,3,4-oxadiazole-2-thiols, X=H, Cl, Br, reacted with ethyl chloroacetate to give S-alkylated compounds. Aminomethylation of the thione form of oxadiazoles yielded N(3)-derivatives. All the products have been characterized by elemental analysis, IR, 1H-NMR and 13C-NMR. The plant-growth regulating effects of the title compounds were examined. From the biological activity results, we found that most compounds showed weak stimulatory activities at low concentrations.

Synthesis and Spectral Characterization of New S-Alkylated 1,2,4-Triazoles as Potential Biological Agents

2017 ◽  
Vol 68 (10) ◽  
pp. 2436-2439
Author(s):  
Stefania Felicia Barbuceanu ◽  
Laura Ileana Socea ◽  
Constantin Draghici ◽  
Elena Mihaela Pahontu ◽  
Theodora Venera Apostol ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Spectral Data ◽  
1H Nmr ◽  
Elemental Analysis ◽  
13C Nmr ◽  
Ethyl Bromide ◽  
Spectral Characterization ◽  
Basic Medium ◽  
Phenacyl Bromide

In the work we presented the behavior of 5-(4-(4-X-phenylsulfonyl)phenyl)-4-(n-propyl)-2H-1,2,4-triazole-3(4H)-thiones (X= Cl or Br) with some alkylation agents. Thus, new S-alkylated 1,2,4-triazole derivatives were synthesized by reaction of the corresponding 1,2,4-triazole-3-thione derivatives with different �-halogenated compounds (ethyl bromide, ethyl chloroacetate or phenacyl bromide), in basic medium. The structures of synthesized compounds were elucidated by spectral data (1H-NMR, 13C-NMR, mass spectrometry) and elemental analysis.

Benzimidazole Derivatives as Potential Antimicrobial and Antiulcer Agents: A Mini Review

2019 ◽  
Vol 19 (16) ◽  
pp. 1292-1297 ◽  
Author(s):  
Ali Mohd Ganie ◽  
Ayaz Mahmood Dar ◽  
Fairooz Ahmad Khan ◽  
Bashir Ahmad Dar
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
1H Nmr ◽  
13C Nmr ◽  
Benzimidazole Derivatives ◽  
Spectroscopic Techniques ◽  
One Pot ◽  
Biological Screening ◽  
Elemental Analyses ◽  
Characterization Studies

:Here in we report the number of strategies for the synthesis of differently substituted benzimidazole derivatives. The protocols involved in the syntheses of these derivatives were one-pot or multi-component. The characterization studies of these derivatives were carried by using different spectroscopic techniques (1H NMR, 13C NMR and MS) and elemental analyses. The biological screening studies revealed that these benzimidazole derivatives show potential antibacterial as well as antifungal behavior. These benzimidazole derivatives not only depicted potential antiulcer properties but also showed moderate to good anticancer/cytotoxic behavior against different cancer cell lines.

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