Preparation of pyridinium salts of 2-furane derivatives

1984 ◽  
Vol 49 (11) ◽  
pp. 2485-2491 ◽  
Author(s):  
Miroslav Kríž ◽  
Jaroslav Kováč ◽  
Vladimír Mlynárik
Keyword(s):  
Nucleophilic Substitution ◽  
Substitution Reaction ◽  
Nmr Spectra ◽  
Nucleophilic Substitution Reaction ◽  
Pyridinium Salts ◽  
H Nmr ◽  
C Nmr

Pyridinium salts have been prepared by nucleophilic substitution reaction of 5-halogeno-2-furane derivatives with pyridine and its 3- and 4-substituted derivatives, where R = 3-methyl, 3-ethyl, 3-amino, 3-methoxycarbonyl, 3-aminocarbonyl, 4-amino, 4-aminocarbonyl, 4-phenoxy, and 3,4-dimethyl, and structure of the derivatives prepared has been confirmed by their 1H NMR and 13C NMR spectra.

Novel lariat calix[4]-1,3-aza-crowns with two branched chains — The excellent phase transfer catalysts for nucleophilic substitution reaction

2010 ◽  
Vol 88 (7) ◽  
pp. 622-627 ◽  
Author(s):  
Fafu Yang ◽  
Yanhua Wang ◽  
Hongyu Guo ◽  
Jianwei Xie ◽  
Zhiqiang Liu
Keyword(s):  
Nucleophilic Substitution ◽  
Substitution Reaction ◽  
Phase Transfer ◽  
Hard Metal ◽  
Nucleophilic Substitution Reaction ◽  
Phenyl Isothiocyanate ◽  
Phase Transfer Catalysts ◽  
H Nmr ◽  
Branched Chains ◽  
New Compounds

By reacting calix[4]-1,3-diethoxylaminoethyl derivative (2) with phenyl isothiocyanate, novel dendritic calix[4]arene derivative (3) with two different branched chains was synthesized in a yield of 78%. By reacting compound 2 with 1,6-diisocyanatohexane or N,N′-bis(2-chloracetamide)ethylene in a “1 + 1” intermolecular addition mode, novel lariat calix[4]-1,3-aza-crowns (4 and 5, respectively) with two branched ethoxyl chains were prepared in reasonable yields. The composition, structures, and conformations of all new compounds were confirmed by elemental analyses, IR, ESI-MS, 1H NMR, and so forth. The liquid–liquid extraction experiments showed that all new hosts possessed good extraction abilities towards soft and hard metal cations. The liquid membrane transport experiments suggested that they had good transport abilities for K+ and Ag+. The experiments of phase transfer catalysis indicated that they possessed excellent catalytic properties of aromatic nucleophilic substitution reaction and benzyl nucleophilic substitution. The optimum yields of products in catalytic reaction were as high as approximately 100%.

Sterically Crowded Heterocycles. I. Molecular Structure of 3-Chain Substituted 2-Phenylimidazo[1,2-a]pyridinium Salts

1994 ◽  
Vol 59 (12) ◽  
pp. 2677-2690 ◽  
Author(s):  
Stanislav Böhm ◽  
Richard Kubík ◽  
Martin Hradilek ◽  
Jan Němeček ◽  
Michal Hušák ◽  
...  
Keyword(s):  
Molecular Structure ◽  
Nmr Spectra ◽  
Molecular Structures ◽  
Pyridinium Salts ◽  
Protonation Site ◽  
X Ray ◽  
H Nmr ◽  
C Nmr ◽  
Pyridinium Perchlorate

2-Phenyl-3-[(Z)-1,3-diphenyl-3-oxopropenyl]imidazo[1,2-a]pyridine (I) was converted to corresponding 1-alkyl-2-phenyl-3-[(Z)-1,3-diphenyl-3-oxopropenyl]imidazo[1,2-a]pyridinium salts III - VI and 2-phenyl- 3-[(Z)-1,3-diphenyl-3-oxopropenyl]imidazo[1,2-a]pyridinium perchlorate (VII). The protonation site is discussed in terms of calculated molecular energies of alternative cations. The X-ray structure analyses of enone I and its quaternary periodide III are reported and compared with the PM3 molecular optimizations. 1H NMR and 13C NMR spectra reveal well changes of molecular structures caused by the transformation of the base I into salts III - VII.

scholarly journals An Improved and Efficient Synthesis of Panobinostat

2018 ◽  
Vol 42 (9) ◽  
pp. 471-473
Author(s):  
Shanwen Chen ◽  
Peiming Zhang ◽  
Huali Chen ◽  
Pu Zhang ◽  
Yu Yu ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Efficient Method ◽  
Industrial Production ◽  
Substitution Reaction ◽  
Efficient Synthesis ◽  
Target Compound ◽  
One Pot ◽  
H Nmr ◽  
C Nmr ◽  
Methyl Phenyl

An improved and efficient method for the synthesis of panobinostat was developed. The commercially available starting material 4-(chloromethyl)benzaldehyde was converted to ( E)-methyl 3-[4-(chloromethyl)phenyl]acrylate via the Wittig–Horner reaction and was then directly condensed with 2-(2-methyl-1 H-indol-3-yl)ethanamine to afford the key intermediate ( E)-methyl 3-[4-({[2-(2-methyl-1 H-indol-3-yl)ethyl]amino}methyl)phenyl]acrylate in a one-pot synthesis reactor. Subsequently a nucleophilic substitution reaction was carried out smoothly to generate the desired compound. The key intermediate and target compound were characterised by HRMS, 1H NMR and 13C NMR. This procedure is operationally simple and would be more suitable for industrial production.

scholarly journals Synthesis, characterization and biological activities of cetirizine analogues

2011 ◽  
Vol 26 (4-5) ◽  
pp. 317-328 ◽  
Author(s):  
Najma Sultana ◽  
M. Saeed Arayne ◽  
Hina Shamshad ◽  
Agha Zeeshan Mirza ◽  
Malik Asia Naz ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Substitution Reaction ◽  
Biological Activities ◽  
Inhibitory Effect ◽  
Nucleophilic Substitution Reaction ◽  
Spectroscopic Techniques ◽  
Activated T Cells ◽  
H Nmr ◽  
Oxidative Burst Response ◽  
Cellular Immune

Cetirizine second generation H1-receptor antagonist is an acid metabolite of hydroxyzine. Present work was based on six new analogues of cetirizine having nucleophilic substitution reaction synthetic pathway. The reactions were proceeded by replacing the scaffold on the cetirizine moiety using nucleophilic substitution reaction. The structures of analogues were confirmed using UV, IR,1H NMR and mass spectroscopic techniques. The analogues were tested for the anti-inflammatory activities on cellular immune response. Oxidative burst response of phagocytes after exposure to the analogues was found to exhibit moderate to significant inhibitory activity (23 to <3.1). However, the compounds as MPC and PPC also showed remarkable inhibitory effect on PHA activated T-cells response and may prove to be lead compounds in therapeutic world.

Conformational structure of ethylene glycol dibenzoate. Vibrational and NMR spectra

1981 ◽  
Vol 46 (8) ◽  
pp. 1913-1929 ◽  
Author(s):  
Bohdan Schneider ◽  
Pavel Sedláček ◽  
Jan Štokr ◽  
Danica Doskočilová ◽  
Jan Lövy
Keyword(s):  
Ethylene Glycol ◽  
Vibrational Spectra ◽  
Nmr Spectra ◽  
Coupling Constants ◽  
Conformational Structure ◽  
Infrared And Raman Spectra ◽  
H Nmr ◽  
Liquid States ◽  
Crystalline Forms ◽  
C Nmr

It was found that three crystalline forms of ethylene glycol dibenzoate can be prepared. Infrared and Raman spectra of these three forms, as well as of the glassy and liquid states, were measured. From 3JHH coupling constants obtained by analysis of the 13C satellite band of the -CH2- group in 1H NMR spectra, and from the 3JCH coupling constants of the -CO.O.CH2- fragment obtained by analysis of the carbonyl band in 13C NMR spectra it was found that in the liquid state the -CH2-CH2- group exists predominantly in the gauche conformational structure, and the bonds C-O-C-C assume predominantly a trans orientation. The results of the analysis of NMR and vibrational spectra were used for the structural interpretation of conformationally sensitive bands in vibrational spectra of ethylene glycol dibenzoate.

The preparation of 3-amino-3-deoxy-1,2-O-isopropylidene-α-L-erythrofuranose, 3-amino-3-deoxy-1,2-O-isopropylidene-β-D-threofuranose and their derivatives

1980 ◽  
Vol 45 (12) ◽  
pp. 3378-3390 ◽  
Author(s):  
Jiří Jarý ◽  
Milena Masojídková ◽  
Ivan Kozák ◽  
Miroslav Marek ◽  
Jan Staněk
Keyword(s):  
Nucleophilic Substitution ◽  
Sodium Azide ◽  
Sodium Benzoate ◽  
Nmr Spectra ◽  
Subsequent Reduction ◽  
H Nmr ◽  
Amino Derivatives

The title amino derivatives VI and XIV were prepared by nucleophilic substitution of p-toluenesulfonyl derivatives II and XVII with sodium azide or hydrazine and subsequent reduction. Nucleophilic substitution of compounds II and XVII with sodium benzoate was also investigated. The 1H NMR spectra of the substances prepared are discussed.

Carbon-13 and nitrogen-14 NMR spectra of 1-(substituted phenyl)pyridinium salts

1980 ◽  
Vol 45 (10) ◽  
pp. 2766-2771 ◽  
Author(s):  
Antonín Lyčka
Keyword(s):  
Heavy Water ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
Coupling Constants ◽  
Pyridinium Salts ◽  
Nmr Signals ◽  
C Nmr

The 13C and 14N NMR spectra of 1M solutions of 1-(substituted phenyl)pyridinium salts (4-CH3, 4-OCH3, H, 4-Cl, 4-Br, 4-I, 3-NO2, 4-NO2, 2,4-(NO2)2 (the 13C NMR only)) have been measured in heavy water at 30 °C. The 13C and 14N chemical shifts, the 1J(CH) coupling constants, some 3J(CH) coupling constants, and values of half-widths Δ 1/2 of the 14N NMR signals are given. The 13C chemical shifts of C(4) correlate with the σ0 constants (δC(4) = (1.79 ± 0.097) σ0 + (147.67 ± 0.041)), whereas no correlation of the nitrogen chemical shifts with the σ constants has been found. The half-widths Δ 1/2 correlate with the σ0 constants (Δ 1/2 = (76.2 ± 4.9) σ0 + (106.4 ± 2.2)) except for 1-phenylpyridinium chloride.

Synthesis and Antituberculotic Activity of Some Substituted 3-Arylamino-5-cyano-2-pyrazinecarboxamides

1995 ◽  
Vol 60 (7) ◽  
pp. 1236-1241 ◽  
Author(s):  
Martin Doležal ◽  
Jiří Hartl ◽  
Antonín Lyčka ◽  
Vladimír Buchta ◽  
Želmíra Odlerová
Keyword(s):  
Nucleophilic Substitution ◽  
Elemental Analysis ◽  
Nmr Spectra ◽  
Substituted Anilines ◽  
H Nmr

Nucleophilic substitution of 3-chloro-5-cyano-2-pyrazinecarboxamide by substituted anilines afforded substituted 3-arylamino-5-cyano-2-pyrazinecarboxamides I-X. The structures of compounds were confirmed by elemental analysis, UV, IR and 1H NMR spectra. The assessment of in vitro antimycotic and antimycobacterial activities of the compounds was carried out. The highest antituberculotic activity against M. tuberculosis in this series was shown by 3-anilino- 5-cyano-2-pyrazinecarboxamide (I), whose efficacy was the same as that of pyrazinecarboxamide.

scholarly journals Synthesis of Carbohydrate Based Macrolactones and Their Applications as Receptors for Ion Recognition and Catalysis

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3394
Author(s):  
Surya B. Adhikari ◽  
Anji Chen ◽  
Guijun Wang
Keyword(s):  
Nucleophilic Substitution ◽  
Supramolecular Chemistry ◽  
Copper Sulfate ◽  
Substitution Reaction ◽  
Biological Properties ◽  
Anion Binding ◽  
Nucleophilic Substitution Reaction ◽  
Binding Properties ◽  
Intramolecular Nucleophilic Substitution ◽  
Leaving Groups

Glycomacrolactones exhibit many interesting biological properties, and they are also important in molecular recognitions and for supramolecular chemistry. Therefore, it is important to be able to access glycomacrocycles with different sizes and functionality. A new series of carbohydrate-based macrocycles containing triazole and lactone moieties have been designed and synthesized. The synthesis features an intramolecular nucleophilic substitution reaction for the macrocyclization step. In this article, the effect of some common sulfonate leaving groups is evaluated for macrolactonization. Using tosylate gave good selectivity for monolactonization products with good yields. Fourteen different macrocycles have been synthesized and characterized, of which eleven macrocycles are from cyclization of the C1 to C6 positions of N-acetyl D-glucosamine derivatives and three others from C2 to C6 cyclization of functionalized D-glucosamine derivatives. These novel macrolactones have unique structures and demonstrate interesting anion binding properties, especially for chloride. The macrocycles containing two triazoles form complexes with copper sulfate, and they are effective ligands for copper sulfate mediated azide-alkyne cycloaddition reactions (CuAAC). In addition, several macrocycles show some selectivity for different alkynes.

Sign in / Sign up

Export Citation Format

Share Document