Preparation and reactions of some substituted pyridinium salts.

by Wing-Kai Yeung

Publisher: University of East Anglia in Norwich

Written in English
Published: Downloads: 701
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Thesis (Ph.D.) - University of East Anglia, School of Chemical Sciences, 1982.

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Open LibraryOL14509432M

As pyridine is often used as an organic base in chemical reactions, pyridinium salts are produced in many acid-base reactions. Its salts are often insoluble in the organic solvent, so precipitation of the pyridinium leaving group complex is an indication of the progress of the reaction. The pyridinium ion also plays a role in Friedel-Crafts ate base: Pyridine. Preparation of the Pyridinium Salts Differing in the Length of the N-Alkyl Substituent.   Method and substances for preparation of N-substituted pyridinium compounds - Roche Diagnostics Operations, Inc. Methods for the synthesis of N-substituted pyridinium compounds by using an N-heteroaryl substituted pyridinium salt (Zincke salt) and reacting it with a nucleophilic amine are provided. In this mini-review authors focused mostly on bioactive properties of pyridinium salts, and main preparations of these compounds such, synthesis pyridinium salts from pyrylium salts via nucleophilic substitution SN(ANRORC), obtaining pyridinium salts via directs arylation, and via Addition at Nitrogen atom, and the last method is synthesis of.

Condensation of a-pyridinium methyl ketone salts and eneones that proceeds through a 2,3-ene-1,5-dione N O R1 N R2 O R2 Br NH4OAc, AcOHR 1 R2 3 O O N F I NH4OAc 90 °C, 3 h 47% N F (Malkov et. al. Tet. Lett. , 42, ) 1-cyanomethylpyridinium salts can also be used to give 2-aminopyridines Kröhnke, Synthesis, , N CN X R1 File Size: KB. Pyridinium p-toluenesulfonate 98% Synonym: p-Toluenesulfonic acid pyridine salt, PPTS, Pyridine p-toluenesulfonate CAS Number Empirical Formula (Hill Notation) C 12 H 13 NO 3 S. Molecular Weight Beilstein/REAXYS Number EC Number MDL number MFCD PubChem Substance ID   Method and substances for the preparation of N-substituted pyridinium compounds - Roche Diagnostics Operations, Inc. Methods for the synthesis of N-substituted carboxylated pyridinium compounds by reaction of a pentamethine precursor .   According to some embodiments, the instant disclosure provides a method for the synthesis of an N-substituted 3-acyl pyridinium compound comprising the steps of a) providing an acyl pentamethinium salt b) reacting the pentamethinium salt of step (a) with a primary amine and c) thereby obtaining an N-substituted 3-acyl pyridinium compound.

  Method and substances for the preparation of N-substituted pyridinium compounds racemization may occur during the nucleophilic displacement reaction. Zincke salts may be prepared by reacting a pyridinium compound with 2,4 dinitro halobenzol preferably with 2,4 dinitrochlorbenzol and 2,4 dinitrobrombenzol. Recent Literature. Addition of Grignard reagents to pyridine N-oxides in THF at room temperature and subsequent treatment with acetic anhydride at °C afforded 2-substituted pyridines in good exchanging acetic anhydride for DMF in the second step, 2-substituted pyridine N-oxides were obtained, enabling the synthesis of 2,6-disubstituted pyridines. They lack side chains and the azacycles share the same oxidation state, but the length of the alkyl chains as well as the number of double bonds in one chain may vary. Most pyridinium salts or cyclostellettamines (A–F, 21–26) carry no double bonds with the exception of the dehydrocyclostellettamines D and E isolated by Fusetani et by: Abstract. A synthetic route to potentially biocidal silsesquioxanes functionalized by quaternary pyridinium functionalities has been developed. N-Alkylation reactions of the precursor compounds 4-(2-(trimethoxysilyl)ethyl)-pyridine (5) and 4-(2-trichloro-silylethyl)pyridine (6) with iodomethane, n-hexylbromide, and n-hexadecylbromide cleanly afforded the corresponding N-alkylpyridinium salts Cited by: 4.

Preparation and reactions of some substituted pyridinium salts. by Wing-Kai Yeung Download PDF EPUB FB2

Makosza et al. reported a method of trifluoromethylation at the 2-position of variably substituted pyridinium salts. The reactions of an alkylpyridinium mesylate salt with alcohols, phenols and thiols to give 3-hydroxypyridinones, compounds known to form strong complexes with hard metal ions, were also disclosed.

Preparation and reactions of some substituted pyridinium salts Author: Yeung, W. ISNI: Awarding Body: University of East Anglia Current Institution: University of East Anglia Date of Award: Availability of Full Text.

Structurally diverse pyridinium salts are quite familiar structures in many natural products and bioactive pharmaceuticals. Over the centuries, these privileged scaffolds have played an intriguing role in a wide range of research topics and, thus, this review aims at highlighting the pyridinium salts in terms of their synthetic routes, reactivity and their importance as pyridinium ionic Cited by: Abstract: Quaternary pyridinium salts with chains ranging from C8to C20belong in the large group of cationic surfactants.

In this paper, the preparation of such cationic surface active agents based on the pyridinium moiety and differing in the length of the N-alkyl chain is Size: 99KB. Quaternary pyridinium salts with chains ranging from C8 to C20 belong in the large group of cationic surfactants.

In this paper, the preparation of such cationic surface active agents based on the pyridinium moiety and differing in the length of the N-alkyl chain is described. Additionally, HPLC technique was established to distinguish each prepared pyridinium by: A novel class of 3-substituted pyridinium salts have been synthesised in high yield by a convenient two-step procedure.

A new synthetic pathway to 1-substituted benzimidazolium salts. Efficient syntheses are developed for several pyrylium cations with substitution patterns more strictly demanding than 2,4,6-triphenyl and these are examined as reagents for the conversion of primary into a leaving group, The 2-mesityl-4,6-diphenyl derivative did not react smoothly with amines.

The 2,6-di-t Cited by: 6 Pyridines and Their Benzo Derivatives: Reactivity at the Ring pyridinium 15 or quinolinium salt 17 in acetic acid in the presence of a catalytic amount of the respective base of the substrate with acrylamide under reflux produced salts 16 and 18 in good Size: 2MB.

The 1-alkylpyridinium salts, which are liquid at rt., so-called ionic liquids, are potential new solvents for synthesis and catalysis8. Several synthetic routes to pyridinium salts are known, but the most commonly used method is the Menschutkin reaction, the SN2 reaction of a pyridine.

desired functionalized pyridinium salt 1 with a free amine function. Scheme 1. Retrosynthesis of pyridinium salts 1. Synthesis of aminopyridines Ketone 5 was easily prepared in two steps from commercially available compounds following established procedures (Scheme 5,62): first, treatment of ethyl acetoacetate 9 with one equivalent.

The current work involved a study of reactions of substituted pyridinium salts with cyanide ion. The substituted pyridinium salts were prepared by the literature methods. The 2- and 3- cyanopyridinium salts reacted with cyanide ion to form 4-cyano-1, : Dorothy N.

Eseonu. 2 or 4-Alkyl ring substituted pyridinium compounds These salts are prepared by the reaction of 2 or 4-alkyl pyridine with alkyl halide at ℃in the absence of solvent for 3 hrs.

The reaction is depicted in Scheme 4. As the chain length of the alkyl group, which is substi-tuted at the ring, is increased higher temperatures and longer. Some substituted benzylidenehydrazinylpyridinium derivatives bearing benzyl, ethylphenyl and propylphenyl groups on the pyridinium nitrogen were synthesized and Cited by: Several steps are typically required including formation of the dihydropyridine, the subsequent reaction with an electrophile, and rearomatization to the desired 3-substituted pyridine.

A similar. concept has been ingeniously employed in a one pot nitration of pyridines in the presence of sulfite as the. Pyridines – Electrophilic Reactions N αααα ββββ γγγγ N E N E E N E E E E −E Pathways for the Electrophilic Aromatic Substitution of Pyridines • The position of the equilibrium between the pyridine and pyridinium salt depends on the substitution pattern and nature of the substituents, but usually favours the saltFile Size: KB.

Pyridinium Salts in Organic Synthesis Elizabeth Cline February 12 Febru Synthesis of trans-2,3-Substituted Piperidines Prior knowledge R1MgX Addition of Grignard results Addition of Grignard and R 1 N OH RT Reaction of Pyridinium Salts with Secondary Amines A N X RNH R2 NH N R A-NH O 2 + R +A-NH 2 N R X A.

Kearney; C File Size: 2MB. Pyridinium salts are commonly formed via N -alkylations of pyridines. Pyridines react with alkyl iodides >, bromides, chlorides >, and triflates > to form the corresponding pyridinium halide or triflate. substituted pyridinium salts as key steps in the preparation of advanced intermediates in numerous synthetic programmes.

Introduction Photochemical reactions can transform structurally simple molecules into compounds with complex skeletons, often with high stereo- and regiocontrol.1 Recently, during a detailed study. Bušić et al., Novel and Cleaner Synthesis of Pyridinium Salts Croat.

Chem. Acta 86 () quaternization reaction were ascertained by performing a series of reactions of pyridoxal. The conditions for the formation of N-substituted aromatic amines in the sulfite variant of recyclization of pyridinium salts, as well as the structural factors that affect the yields of the final substances, were : G.

Shkil, O. Khristolyubova, B. Lugovik, E. Atavin, R. Sagitullin. An efficient synthetic procedure for the preparation of the unusual charge-separated pyridinium-Meldrum acid and N,N-dimethylbarbiturate acid zwitterionic salts was developed though a unique one-pot four-component reaction involving pyridine, aromatic aldehyde, Meldrum acid or N,N-dimethylbarbituric acid, and p-nitrobenzyl bromide in acetonitrile.

By varying combinations of four Cited by: An efficient synthetic procedure for the preparation of the unusual charge-separated pyridinium-Meldrum acid and N,N-dimethylbarbiturate acid zwitterionic salts was developed though a unique one-pot four-component reaction involving pyridine, aromatic aldehyde, Meldrum acid or N,N-dimethylbarbituric acid, and p-nitrobenzyl bromide in by:   On basis of earlier experimental experience, the transfer of protons in salts of the organic cation-inorganic anion type occurs primarily through directional arrangement of the anion-anion type short hydrogen bonds.

The submitted work presents the preparation of quaternary pyridinium salts of inorganic hydrogen anions in the absence of solvent molecules in their crystal by: 1. para-substituted toluenes or para-substituted aromatic aldehydes, one can obtain 4,disubstituted stilbenes. This reaction is relatively simple but has low yield.

As an example, condensation of 2,4-dinitrotoluene and 4-nitrophenylacetic acid with aromatic aldehyde was studied [26]. The reaction involves carbanion addition to the carbonyl Size: 1MB. The reactions of 2- or 4-cyanopyridinium salts with active methylene compounds such as dimethyl malonate, malononitrile, and cyclohexane-1,3-dione affording 2- or 4-(substituted.

Show Summary Details. More options Chemical PapersCited by: 1. row equations. Equation 1 in the third row illustrates a general preparation of substituted furans, pyrroles and thiophenes from 1,4-dicarbonyl compounds, known as the Paal-Knorr synthesis. Many other procedures leading to substituted heterocycles of this kind have been devised.

Two of these are shown in reactions 2 and Size: KB. Chemical properties. Like other oxonium ions, pyrylium is unstable in neutral r, pyrylium is much less reactive than ordinary oxonium ions because of aromatic stabilization.

The 2,4,6-triphenyl salt is commonly reacted with aliphatic amines at the 1 position, forming pyridinium salts and activating them towards oxidative addition by metal complexes, most notably ones with : CHEBI We have used highly substituted pyrylium salts for the two‐step conversion of the amino group in alkylamines RNH 2 into numerous other functionalities.

In the first step, the pyrylium salts are converted with the amines into N ‐substituted pyridinium salts, which, in the second step, react with Nu ⊖ to give the desired products by: Synthesis and Characterizations of Pyridinium Salts Including Poly(pyridinium salt)s and Their Applications by Tae Soo Jo Dr.

Pradip K. Bhowmik, Examination Committee Chair Department of Chemistry University of Nevada La Vegas Pyridinium salts, both molecular and polymeric, are an interesting class ofCited by: 2. Title:Bio-Active Pyridinium Salts: A Mini-Review on Properties and Selected Reactions VOLUME: 16 ISSUE: 7 Author(s):Andrzej Günther* and Robert Pełech Affiliation:Institute of Organic Chemical Technology, Faculty of Chemical Technology and Engineering, West Pomeranian University of Technology, Szczecin, Institute of Organic Chemical Technology, Faculty of Chemical Technology Author: Andrzej Günther, Robert Pelech.

Pyridinium salts are involved in a wide variety of synthetically useful reactions. Many workers utilized the electrophilic nature of the pyridinium salts to incorporate substitution into the pyridine scaffold.Upon heating a primary amine with the N-2,4-dinitrophenyl-pyridinium salt (2), the addition of the amine leads to the opening of the pyridinium ring.A second addition of amine leads to the displacement of 2,4-dinitroaniline (5) and formation of the König salt [4] (6a and 6b).The trans-cis-trans isomer of the König salt (6a) can react by either sigmatropic rearrangement or nucleophilic.