Vilsmeier haack rxn
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its an rearrangement reaction of organic compound. in this rearrangment rxn amide and pcl4 is react with arene for aryl ketone or aryl amide.
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Vilsmeier haack reaction
The Vilsmeier-Haack reaction involves treating an electron-rich aromatic or heterocyclic system with a Vilsmeier reagent, which is formed from an amide like DMF and POCl3, to install a formyl group. The reaction proceeds through an iminium intermediate and takes place around 100°C in a solvent like DCM over 10-24 hours. It is useful for synthesizing aldehydes and ketones from electron-rich aromatic and heterocyclic substrates.
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A group the use of which makes possible to react a less reactive functional group selectively in presence of a more reactive group is known as protecting group.
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This document summarizes several organic reactions used in heterocyclic chemistry. It describes the Debus–Radziszewski reaction for imidazole synthesis, the Knorr reaction for pyrrole synthesis, the Pinner reaction for pyrimidine synthesis, the Combes reaction for quinoline synthesis, the Bernthsen reaction for acridine synthesis, the Smiles rearrangement, and the Traube reaction for purine synthesis. For each reaction, it provides the starting materials, product, mechanism, and some applications. The document is intended to present an overview of important heterocyclic reactions for students of pharmaceutical chemistry.
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The document describes the Ugi reaction, a multi-component reaction where a ketone or aldehyde, amine, isocyanide, and carboxylic acid come together to form a bis-amide. It was first reported in 1959 by Ivar Karl Ugi. The reaction has high atom economy and yields, occurs rapidly at room temperature, and is uncatalyzed. It has applications in synthesizing chemical libraries and multiple compounds in one step, such as the HIV drug Crixivan. The mechanism involves imine formation, proton exchange, additions of the isocyanide and carboxylic acid, and a Mumm's rearrangement.
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The document discusses transition metals and their properties and uses. It defines transition metals based on their electronic configuration and partially filled d subshells. It describes how transition metals can adopt multiple oxidation states, form complexes, exhibit catalytic activity, and be used in organic reactions like cross-coupling reactions. Common transition metal catalysts used in coupling reactions include palladium and nickel. Organocatalysis is also discussed as an alternative to metal-based catalysis.
Brook rearrangement
It is an intramolecular rearrangement reaction in which the 1,2-migration of silyl group from carbon to oxygen under basic conditions.It involves the formation of a pentacoordinate siliconintermediate.Discovered by Adrian Gibbs Brook in 1958.
Ullmann reaction
The Ullmann reaction involves the condensation of aryl halides in the presence of finely divided copper or copper bronze at an elevated temperature to form diaryl derivatives. Two proposed mechanisms are the free radical mechanism, where copper generates an aryl radical, and the ionic mechanism, where an organocuprate intermediate is formed. The Ullmann reaction is useful for synthesizing biaryls, polyaryls, diaryl amines, diaryl ethers, and gossypol.
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The document discusses several heterocyclic compounds including quinolines, isoquinolines, and indoles. It summarizes key reactions used to synthesize these compounds, including the Combes, Friedlander, Knorr, and Skraup reactions for quinoline synthesis. It also discusses the Bischler-Napieralski, Pictet-Spengler, and Pomeranz-Fritsch reactions for isoquinoline synthesis and the Fischer, Madelung, and Reissert reactions for indole synthesis, along with mechanisms and examples of each reaction. Reactivity and substitution patterns are also covered for quinolines, isoquinolines and indoles.
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The document discusses the Ugi reaction, a multi-component reaction first reported in 1959 by Prof. Ivar Karl Ugi. The Ugi reaction involves a ketone or aldehyde, an amine, an isocyanide, and a carboxylic acid to form a bis-amide derivative. It is exothermic, fast, and high-yielding. By varying the substituents, large chemical libraries can be synthesized from a single reaction. The Ugi reaction is used in combinatorial chemistry and drug development, such as for the HIV drug Crixivan.
Role of chirality in stereoselective and specific theraputic agent
This document discusses the role of chirality in selective therapeutic agents. It begins by defining isomerism and the different types of isomers including constitutional, stereoisomers, optical isomers, enantiomers, and diastereomers. It then discusses the discovery of optical activity and chirality. The key points are that humans are chiral beings and the enantiomers of chiral drugs may have different biological effects. Several examples are given to illustrate how the biological activity of enantiomers can differ, including some being more active, having opposing effects, or one causing toxicity. The importance of understanding chirality in drug development and safety is emphasized.
Suzuki reaction
The Suzuki reaction is a palladium-catalyzed cross-coupling reaction between boronic acids or esters with organic halides, triflates, or other boron-containing compounds. This reaction occurs under basic conditions and leads to the formation of carbon-carbon single bonds, typically between an aryl or vinyl group and another aryl or vinyl group. It is commonly used to synthesize biaryl compounds. The reaction proceeds through oxidative addition, transmetallation, and reductive elimination steps. Key advantages are mild reaction conditions and availability of boronic acids. The Suzuki reaction has applications in synthesizing pharmaceuticals, agrochemicals, and natural products.
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When there are two functional groups of unequal reactivity within a molecule, the more reactive group can be made to react alone, but it may not be possible to react the less reactive functional group selectively.
A group the use of which makes possible to react a less reactive functional group selectively in presence of a more reactive group is known as protecting group.
A protecting group blocks the reactivity of a functional group by converting it into a different group which is inert to the conditions of some reaction(s) that is to be carried out as part of a synthetic route
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Aromatic electrophilic substitution mishu
1. Electrophilic aromatic substitution is the characteristic reaction of benzene rings. A hydrogen atom is replaced by an electrophile through a two-step mechanism involving a resonance-stabilized cyclohexadienyl carbocation intermediate.
2. Substituents on benzene rings activate or deactivate the ring towards electrophilic aromatic substitution by influencing the stability of the carbocation intermediate. Electron-donating groups activate the ring while electron-withdrawing groups deactivate it.
3. The identity of existing substituents determines the orientation of new substituents, favoring either ortho/para or meta positions in electrophilic aromatic substitution.
Electrophilic aromatic substitution reactions
This is Power Point Presentation on Topic "Electrophilic Aromatic Substitution Reactions" as per syllabus of "University of Mumbai" for S.Y. B. Pharmacy (Sem.: IV) students.
Aromatic Electrophilic Substitution Reactions
The document discusses various aromatic electrophilic substitution reactions including Vilsmeier-Haack formylation, Reimer-Tiemann reaction, Gattermann-Koch formylation, and Kolbe-Schmitt reaction. It provides details on the reaction conditions, mechanisms, substrates used, and products formed for each reaction. It also discusses some exceptions and problems related to these reactions.
aromatic reactions.pptx
The document discusses aromatic electrophilic substitution reactions including the Vilsmeier-Haack formylation, Reimer-Tiemann reaction, Gattermann-Koch formylation, and diazo coupling reactions. It provides background on the reactions, their mechanisms, substrates used, and factors that influence product distribution. Examples and problems are also given to illustrate the application of these reactions in synthesis.
B.tech. ii engineering chemistry unit 4 B organic chemistry
Organic reactions and their mechanisms are described. Key topics covered include nucleophiles and electrophiles, reaction types (addition, elimination, substitution), and organic intermediates. Electron displacement effects such as inductive, mesomeric, electromeric and inductometric effects are also discussed. Common organic reactions like nitration, halogenation and nucleophilic aromatic substitution are summarized.
Effect of conformation on reactivity
This document discusses the effect of conformation on the reactivity of acyclic and cyclic compounds. It provides examples of how the conformation of a compound, whether the substituents are equatorial or axial, can impact the rate and outcome of various chemical reactions including E2 eliminations, SN1 and SN2 substitutions, esterification, hydrolysis, elimination reactions, molecular rearrangements, neighboring group participation, and oxidation reactions. Specifically, it notes that equatorial substituents are often more reactive than axial substituents due to differences in steric hindrance and stereoelectronic effects. Reaction rates and products can differ significantly between conformational isomers of the same compound.
nuecleophilic addition to c=o
1. Nucleophilic addition reactions to the carbonyl group (C=O) of aldehydes and ketones are important reactions. The carbonyl carbon is electrophilic due to the electron-withdrawing oxygen atoms.
2. Common reactants that undergo nucleophilic addition to the carbonyl group include alcohols, thiols, amines, organometallic reagents (e.g. Grignard reagents), enolates, and water. The reaction can proceed through an acid or base catalyzed mechanism.
3. Important carbonyl addition reactions discussed include aldol condensation, Cannizzaro reaction, Wittig reaction, Reformatsky reaction, and reduction of carbon
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Vilsmeier haack rxn
- 1. VILSMEIER-HAACK REACTION Presented by Sukanta Debnath M.Pharm 1st year Presented to Dr. Pratap Ch. Acharya (Head of the Dept.) Tripura University Presentation on Advance Organic Chemistry -1
- 2. CONTENTS:- • Introduction • Reaction • Mechanism • Application • References
- 3. Introduction:- • The vilsmeier-haack reaction (also called vilsmeier reaction) is the chemical reaction of substituted amide with phosphorus oxychloride and electron rich arene to produce aryl aldehyde or ketone. • This reaction is named after Anton Vilsmeier and Albrecht Haack. • The reaction of a substituted amide with phosphorus oxychloride gives a substituted chloroiminium ion also called Vilsmeier Reagent
- 4. Reaction:- O CH3 N H CH3 O + O CH3 O + PoCl3 H2O Anisole N –methyl N-phenyl formamide 2-methoxybenzaldehyde N H CH3 N-methylaniline (Secondary aniline)
- 5. Mechanism:- • Step:-1 (Generation of electrophile) N H CH3 O + P Cl Cl Cl O N + CH3 H O P Cl Cl O + Cl – N C + CH3 H Cl + P Cl Cl O O – Chloroiminium ion
- 6. Mechanism :- • Step:- 2 (Attack of electrophile) O CH3 + N C + CH3 H Cl H + O C H3 N CH3 Cl H O + C H3 N CH3 Cl H O C H3 H H N + CH3 Cl – O H H O H2 O C H3 N CH3 H O H O C H3 O H N H CH3
- 7. Applications:- • Formylation of aromatic hydrocarbons, phenols,ketones,phenolsethers. • Synthesis of pyrroles. • Synthesis of pyrimidines. • Synthesis of pyrazoles. • Synthesis of Quinolines and Indoles.
- 8. References:- • Synthetic Strategies Towards Vilsmeier-Haack Reaction • https://en.wikipedia.org/wiki/Vilsmeier%E2%80%93Haac k_reaction • Reddy, M. P.; Rao, G. S. K. J. Chem. Soc., Perkin Trans. 1 1981, 2662–2665.CrossRefGoogle Scholar
Editor's Notes
- INTRO
- CONTENTS
- DEFINATIONS
- REACTIONS
- MECHANISM
- MECHANISM