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Total synthesis of Sterpurenone New, Total Synthesis of (훽)-Cyperolone, Protecting Group-Free Total Synthesis of (−)-Lannotinidine B, Enantiospecific Total Synthesis of the (−)-Presilphiperfolan-8-ol, Enantioselective Total Synthesis of (−)-Pavidolide B, total synthesis of Eupalinilide E
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Heterocyclic compounds pyrazole
Heterocyclic compounds pyrazoleMinal Saini , student of Chaudhary bansilal University , Bhiwani, Haryana
Pyrazoles having two groups of nitrogens one of them is basic and another one is neutral. It have anti cancer , anti microbial properties. Michael addition reaction
Michael addition reaction involves the conjugate addition of a nucleophile to an α,β-unsaturated carbonyl compound. It proceeds through a reversible 1,2-addition of the nucleophile to the β-carbon, which can then undergo irreversible proton elimination to form the more stable thermodynamic enolate product by removing the π-bond of the C=C. This reaction is useful for forming C-C bonds and natural products, with examples given of its application in multi-step syntheses using further carbonyl reactions like aldol condensation.
Shapiro reaction
This document discusses the Shapiro reaction, which was discovered by Robert H. Shapiro in 1967. The reaction involves converting aryl sulfonyl hydrazones of aldehydes and ketones into olefins using alkyl lithium reagents, grignard reagents, or alkali metal amides at -78°C. The reaction mechanism proceeds through deprotonation, elimination, and loss of nitrogen to form alkenyl intermediates. The Shapiro reaction has been used in the total synthesis of natural products like phytocassane D and in the formation of ring B in the Nicolaou Taxol total synthesis.
Unit 4 Pyrazole
This document discusses heterocyclic compounds, specifically pyrazoles. It describes pyrazoles as a 5-membered heterocyclic ring containing two nitrogen atoms at the 1st and 2nd positions. Several common synthesis routes for pyrazoles are outlined, including the Paal-Knorr synthesis using 1,3-dicarbonyl compounds and hydrazines. The document also reviews reactions that pyrazoles undergo, such as electrophilic substitution, oxidation, and reduction. Finally, some medicinal uses of pyrazoles are provided, including their use as anti-pyretic, analgesic, and anti-inflammatory drugs.
Heterocyclic Organic Reaction - By Vishal Dakhale
This document discusses three heterocyclic organic reactions: the Debus-Radziszewski imidazole synthesis, the Knorr pyrazole synthesis, and the Combes quinoline synthesis. The Debus-Radziszewski reaction synthesizes imidazoles from a dicarbonyl, aldehyde, and ammonia. The Knorr reaction synthesizes pyrazoles from hydrazines and 1,3-dicarbonyl compounds using an acid catalyst. The Combes reaction synthesizes quinolines by condensing unsubstituted anilines with β-diketones followed by an acid-catalyzed ring closure.
Hypervalent organo iodines reagents in organic synthesis
Hypervalent organo iodines reagents in organic synthesisMinal Saini , student of Chaudhary bansilal University , Bhiwani, Haryana
Hypervalent refers to the main group elements that breaks the octet rule and firmly has more than right electrons in it's valence shell. These are non - metallic oxidation reagents. Organic Name Reaction With Their Respective Mechanism
The document summarizes three organic name reactions - Combes quinoline synthesis, Knorr pyrazole synthesis, and Pinner pyrimidine synthesis - and their respective mechanisms. The Combes quinoline synthesis involves the condensation of anilines and β-diketones to form quinolines via an acid-catalyzed ring closure. The Knorr pyrazole synthesis converts hydrazines or derivatives with 1,3-dicarbonyl compounds to pyrazoles using an acid catalyst in a three step mechanism. The Pinner pyrimidine synthesis involves the condensation of 1,3-dicarbonyl compounds with amidines catalyzed by acids or bases
Knorr Pyrazole Synthesis (M. Pharm)
The document discusses the Knorr pyrazole synthesis reaction which converts hydrazines or derivatives and 1,3-dicarbonyl compounds to pyrazoles using an acid catalyst. The mechanism involves acid-catalyzed imine formation on either carbonyl carbon, followed by attack of the other nitrogen on the other carbonyl group. This forms a diimine compound which deprotonates to generate the final pyrazole product. Several examples of pyrazoles synthesized using this reaction are mentioned, including antipyrine, celecoxib, and metamizole sodium which have various medical applications.
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Heterocyclic compounds pyrazole
Heterocyclic compounds pyrazoleMinal Saini , student of Chaudhary bansilal University , Bhiwani, Haryana
Pyrazoles having two groups of nitrogens one of them is basic and another one is neutral. It have anti cancer , anti microbial properties. Michael addition reaction
Michael addition reaction involves the conjugate addition of a nucleophile to an α,β-unsaturated carbonyl compound. It proceeds through a reversible 1,2-addition of the nucleophile to the β-carbon, which can then undergo irreversible proton elimination to form the more stable thermodynamic enolate product by removing the π-bond of the C=C. This reaction is useful for forming C-C bonds and natural products, with examples given of its application in multi-step syntheses using further carbonyl reactions like aldol condensation.
Shapiro reaction
This document discusses the Shapiro reaction, which was discovered by Robert H. Shapiro in 1967. The reaction involves converting aryl sulfonyl hydrazones of aldehydes and ketones into olefins using alkyl lithium reagents, grignard reagents, or alkali metal amides at -78°C. The reaction mechanism proceeds through deprotonation, elimination, and loss of nitrogen to form alkenyl intermediates. The Shapiro reaction has been used in the total synthesis of natural products like phytocassane D and in the formation of ring B in the Nicolaou Taxol total synthesis.
Unit 4 Pyrazole
This document discusses heterocyclic compounds, specifically pyrazoles. It describes pyrazoles as a 5-membered heterocyclic ring containing two nitrogen atoms at the 1st and 2nd positions. Several common synthesis routes for pyrazoles are outlined, including the Paal-Knorr synthesis using 1,3-dicarbonyl compounds and hydrazines. The document also reviews reactions that pyrazoles undergo, such as electrophilic substitution, oxidation, and reduction. Finally, some medicinal uses of pyrazoles are provided, including their use as anti-pyretic, analgesic, and anti-inflammatory drugs.
Heterocyclic Organic Reaction - By Vishal Dakhale
This document discusses three heterocyclic organic reactions: the Debus-Radziszewski imidazole synthesis, the Knorr pyrazole synthesis, and the Combes quinoline synthesis. The Debus-Radziszewski reaction synthesizes imidazoles from a dicarbonyl, aldehyde, and ammonia. The Knorr reaction synthesizes pyrazoles from hydrazines and 1,3-dicarbonyl compounds using an acid catalyst. The Combes reaction synthesizes quinolines by condensing unsubstituted anilines with β-diketones followed by an acid-catalyzed ring closure.
Hypervalent organo iodines reagents in organic synthesis
Hypervalent organo iodines reagents in organic synthesisMinal Saini , student of Chaudhary bansilal University , Bhiwani, Haryana
Hypervalent refers to the main group elements that breaks the octet rule and firmly has more than right electrons in it's valence shell. These are non - metallic oxidation reagents. Organic Name Reaction With Their Respective Mechanism
The document summarizes three organic name reactions - Combes quinoline synthesis, Knorr pyrazole synthesis, and Pinner pyrimidine synthesis - and their respective mechanisms. The Combes quinoline synthesis involves the condensation of anilines and β-diketones to form quinolines via an acid-catalyzed ring closure. The Knorr pyrazole synthesis converts hydrazines or derivatives with 1,3-dicarbonyl compounds to pyrazoles using an acid catalyst in a three step mechanism. The Pinner pyrimidine synthesis involves the condensation of 1,3-dicarbonyl compounds with amidines catalyzed by acids or bases
Knorr Pyrazole Synthesis (M. Pharm)
The document discusses the Knorr pyrazole synthesis reaction which converts hydrazines or derivatives and 1,3-dicarbonyl compounds to pyrazoles using an acid catalyst. The mechanism involves acid-catalyzed imine formation on either carbonyl carbon, followed by attack of the other nitrogen on the other carbonyl group. This forms a diimine compound which deprotonates to generate the final pyrazole product. Several examples of pyrazoles synthesized using this reaction are mentioned, including antipyrine, celecoxib, and metamizole sodium which have various medical applications.
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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.
Michael addition reaction
The document discusses the Michael addition reaction, which involves the nucleophilic addition of a carbanion to an α,β-unsaturated carbonyl compound. It provides the definition, mechanism, examples including the synthesis of warfarin, and applications such as asymmetric Michael reactions. The mechanism involves deprotonation of the carbonyl compound by a base to form an enolate ion, which adds to the Michael acceptor to form a new carbon-carbon bond via 1,4-addition.
Organic chemistry reactions
The document provides information about various organic chemistry reactions including the Baeyer-Villiger oxidation, Shapiro reaction, Suzuki coupling, ozonolysis, and Michael reaction. It discusses the reaction mechanisms, applications in synthesis, and key steps for each reaction. Examples are given of uses in synthesizing natural products and complex molecules.
Organic reaction
This document summarizes four organic reactions:
1. The Mitsunoba reaction converts alcohols to esters, acids, or ethers using triphenylphosphine and diethyl azodicarboxylate. It proceeds through an oxyphosphonium ion intermediate and inversion of stereochemistry.
2. The Mannich reaction aminomethylates carbonyl compounds with formaldehyde and a primary or secondary amine to form beta-amino carbonyl compounds. It involves initial formation of an iminium ion.
3. The Vilsmeier-Haack reaction uses phosphorus oxychloride to convert substituted amides to chloroiminium ions which react with arenes to form aromatic al
knorr pyrazole synthesis
The Knorr pyrazole synthesis converts a hydrazine or its derivatives and a 1,3-dicarbonyl compound to a pyrazole using an acid catalyst. The mechanism involves an acid-catalyzed imine formation where the hydrazine attacks either carbonyl carbon, followed by attack of the other nitrogen on the other carbonyl group. This diimine compound then deprotonates to form the pyrazole product. The reaction is used to synthesize compounds such as metal chelates, photographic dyes, herbicides, and biologically active molecules.
Metathesis
This document discusses metathesis reactions and their applications in organic synthesis. It begins with definitions and examples of different types of metathesis reactions including alkene, alkyne, and enyne metathesis. It then covers the key catalysts used, such as Grubbs and Schrock catalysts, as well as the 2005 Nobel Prize awarded for the development of metathesis reactions. The document concludes by outlining several important applications of metathesis in synthesizing biologically active compounds and natural products.
retrosynthesis
more chemistry contents are available
1. pdf file on Termmate: https://www.termmate.com/rabia.aziz
2. YouTube: https://www.youtube.com/channel/UCKxWnNdskGHnZFS0h1QRTEA
3. Facebook: https://web.facebook.com/Chemist.Rabia.Aziz/
4. Blogger: https://chemistry-academy.blogspot.com/
Organic Synthesis:
The Disconnection Approach
One Group C-C Disconnection of Alcohol and Alkene
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more chemistry contents are available
1. pdf file on Termmate: https://www.termmate.com/rabia.aziz
2. YouTube: https://www.youtube.com/channel/UCKxWnNdskGHnZFS0h1QRTEA
3. Facebook: https://web.facebook.com/Chemist.Rabia.Aziz/
4. Blogger: https://chemistry-academy.blogspot.com/
Organic Synthesis:
The Disconnection Approach
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Suzuki and Shapiro reaction
The document summarizes the Suzuki and Shapiro reactions. The Suzuki reaction involves a palladium-catalyzed cross-coupling between organoboron compounds and organic halides to form carbon-carbon bonds. It proceeds through oxidative addition, transmetallation, and reductive elimination steps. The Shapiro reaction involves the base-catalyzed decomposition of tosyl hydrazones to form olefins. Both reactions have been used in the synthesis of various drugs and natural products.
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This document discusses the Sharpless epoxidation reaction for asymmetric epoxidation of allylic alcohols. It provides details on the reaction's discovery in 1980, its broad substrate scope and high enantioselectivity. The document also reviews modifications like using molecular sieves or polymer supports, and applications in natural product total syntheses like venustatriol and amphotericin B. Finally, it summarizes other methods for enantioselective epoxidation and recommends the best methods depending on substrate type.
Retrosynthesis
Retrosynthetic analysis is a technique for planning organic syntheses by systematically deconstructing a target molecule into simpler precursor structures through disconnections, with the goal of arriving at commercially available starting materials. Key criteria for good disconnections include a favorable mechanism, maximizing simplification at each step, and producing recognizable starting materials. Common disconnections involve breaking bonds between functional groups like alcohols, alkenes, ketones, acids, and saturated/aromatic hydrocarbons. Protection and activation of reactive groups is sometimes required to control reaction selectivity. Proper application of retrosynthesis allows complex multi-step syntheses to be planned systematically and increases the likelihood of success.
100 named reactions
100 named reactions with examples of total syntheses which utilized these reactions, with reaction conditions. with included references for each syntheses.
organic reaction
The document summarizes two organic reactions: the Dieckmann reaction and ozonolysis reaction. The Dieckmann reaction involves the intramolecular condensation of diesters in the presence of a strong base to form β-keto esters via a 5-exo-trig cyclization. It is used to synthesize cyclopentane and cyclohexane derivatives. Ozonolysis involves the cleavage of unsaturated bonds like alkenes and alkynes with ozone to form carbonyl groups. It can be used to oxidize alkenes into alcohols, aldehydes, ketones or carboxylic acids and is useful for structure elucidation of unknown compounds containing carbon-carbon double bonds.
Lysozyme Enzymology
1. Lysozyme attaches to bacterial cell walls and uses its Glu 35 residue to transfer a proton to cleave the bond between the D- and E-rings of the cell wall, forming an oxonium ion transition state.
2. The Asp 52 carboxylate group then nucleophilically attacks the electron-poor carbon of the D-ring to form a glycosyl-enzyme intermediate.
3. Hydrolysis of this intermediate by Glu 35, forming another transition state, completes the catalytic cycle and releases the D-ring product.
Quinoline
1. Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N. It is colorless and hygroscopic, becoming yellow and brown over time when exposed to light.
2. Quinoline itself has few applications but many derivatives are useful, including quinine which is an important anti-malarial drug. Over 200 biologically active quinoline alkaloids have been identified.
3. The document discusses the structure, properties, synthesis methods like Skraup, Doebner-Miller, and Conrad-Limpach, reactions including electrophilic substitution, oxidation, and reduction, and applications of quinoline and its derivatives in dyes
Organic reaction
This document summarizes several organic reactions including the Mannich reaction, ozonolysis, Mitsunobu reaction, and Baeyer-Villiger oxidation. It provides the mechanisms and synthetic applications of each reaction. The Mannich reaction involves the condensation of an active methyl group in a ketone. Ozonolysis is used to cleave carbon-carbon double bonds and locate their position. The Mitsunobu reaction converts alcohols to other functional groups like esters with inversion of stereochemistry. Baeyer-Villiger oxidation uses a peroxycarboxylic acid to convert a ketone to an ester.
pyrazole ...by saikat hossain....SEU
The document discusses various methods for synthesizing pyrazoles, including the Knorr pyrazole synthesis, reactions involving α,β-unsaturated aldehydes, β-hydroxy ketones, aromatic aldehydes, vinyl ketones, and more. It also covers pharmacological activities of pyrazoles such as antibacterial, antifungal, anticancer, anti-inflammatory, and anti-viral properties. Specific compounds are mentioned that have shown effectiveness against various bacterial, fungal, and viral strains. A wide range of synthetic routes and biological activities of pyrazoles and their derivatives are presented.
Baeyer-Villiger Oxidation
This is a brief introduction to the Baeyer-Villiger Oxidation/Rearrangement in the form of a micro-presentation.
The Baeyer-Villiger Oxidation is useful in the synthesis of esters and lactones. Consult the pdf file for more information.
You are encouraged to visit :
http://www.harinchem.com/named_organic_reactions.html to view a flash micro movie of the mechanism.
Please send feedback or questions through:
http://www.harinchem.com/contactpage.aspx.
The importance of lactone synthesis is underscored by its presence in diverse molecules of pharmacological significance, including statins (HMG CoA reductase inhibitors).
Mannich Reaction
The document discusses various nitrogen substitution and addition reactions including the Mannich reaction where nucleophilic nitrogen adds to saturated or unsaturated carbons. It specifically mentions the reaction of primary amines with aldehydes and ketones to form imines and the formation of amino acids through reactions like the Hell-Volhard Zelensky reaction, Gabriel procedure, nitrosation, and Strecker method.
Important Name reaction
Name reactions:Clemmensen reduction, Darzens condensation, Diels Alder, Eschweiler-Clarke, Friedel-Crafts, Grinard, HofmanMannich, Michael, Meerwin- Pondorf- Verley, Perkin, Reformatsky, Reimer-Tiemann,, Witting and Wolf-Kishner reduction, Aldol condensation.
Cheng 2015
This document describes a one-pot, three-component reaction to synthesize densely substituted benzofurans from methyl ketones, phenols, and nucleophiles. Specifically, it details:
1) The reaction of phenylglyoxal monohydrate, phenols like sesamol, and indoles produces benzofurans in good to excellent yields with acid catalysis.
2) Replacing phenylglyoxal with methyl ketones and using I2/DMSO allows an in situ generation of arylglyoxal from the methyl ketone for the reaction.
3) Various substituted benzofurans can be synthesized from different methyl ketones, phenols
Sigmatropic reaction
The document defines and provides examples of various sigmatropic reactions, including:
1. The Claisen rearrangement, which involves the [3,3] rearrangement of an allyl vinyl ether.
2. The Cope rearrangement, which involves the [3,3] sigmatropic rearrangement of 1,5-dienes.
3. The Oxy-Cope rearrangement, which has a hydroxyl substituent and proceeds faster when deprotonated.
4. Other reactions discussed include the Fischer indole synthesis, aromatic Claisen rearrangement, [2,3]-Wittig rearrangement, Carroll rearrangement, and walk rearrangements. Mechanisms
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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.
Michael addition reaction
The document discusses the Michael addition reaction, which involves the nucleophilic addition of a carbanion to an α,β-unsaturated carbonyl compound. It provides the definition, mechanism, examples including the synthesis of warfarin, and applications such as asymmetric Michael reactions. The mechanism involves deprotonation of the carbonyl compound by a base to form an enolate ion, which adds to the Michael acceptor to form a new carbon-carbon bond via 1,4-addition.
Organic chemistry reactions
The document provides information about various organic chemistry reactions including the Baeyer-Villiger oxidation, Shapiro reaction, Suzuki coupling, ozonolysis, and Michael reaction. It discusses the reaction mechanisms, applications in synthesis, and key steps for each reaction. Examples are given of uses in synthesizing natural products and complex molecules.
Organic reaction
This document summarizes four organic reactions:
1. The Mitsunoba reaction converts alcohols to esters, acids, or ethers using triphenylphosphine and diethyl azodicarboxylate. It proceeds through an oxyphosphonium ion intermediate and inversion of stereochemistry.
2. The Mannich reaction aminomethylates carbonyl compounds with formaldehyde and a primary or secondary amine to form beta-amino carbonyl compounds. It involves initial formation of an iminium ion.
3. The Vilsmeier-Haack reaction uses phosphorus oxychloride to convert substituted amides to chloroiminium ions which react with arenes to form aromatic al
knorr pyrazole synthesis
The Knorr pyrazole synthesis converts a hydrazine or its derivatives and a 1,3-dicarbonyl compound to a pyrazole using an acid catalyst. The mechanism involves an acid-catalyzed imine formation where the hydrazine attacks either carbonyl carbon, followed by attack of the other nitrogen on the other carbonyl group. This diimine compound then deprotonates to form the pyrazole product. The reaction is used to synthesize compounds such as metal chelates, photographic dyes, herbicides, and biologically active molecules.
Metathesis
This document discusses metathesis reactions and their applications in organic synthesis. It begins with definitions and examples of different types of metathesis reactions including alkene, alkyne, and enyne metathesis. It then covers the key catalysts used, such as Grubbs and Schrock catalysts, as well as the 2005 Nobel Prize awarded for the development of metathesis reactions. The document concludes by outlining several important applications of metathesis in synthesizing biologically active compounds and natural products.
retrosynthesis
more chemistry contents are available
1. pdf file on Termmate: https://www.termmate.com/rabia.aziz
2. YouTube: https://www.youtube.com/channel/UCKxWnNdskGHnZFS0h1QRTEA
3. Facebook: https://web.facebook.com/Chemist.Rabia.Aziz/
4. Blogger: https://chemistry-academy.blogspot.com/
Organic Synthesis:
The Disconnection Approach
One Group C-C Disconnection of Alcohol and Alkene
Organic Synthesis:
more chemistry contents are available
1. pdf file on Termmate: https://www.termmate.com/rabia.aziz
2. YouTube: https://www.youtube.com/channel/UCKxWnNdskGHnZFS0h1QRTEA
3. Facebook: https://web.facebook.com/Chemist.Rabia.Aziz/
4. Blogger: https://chemistry-academy.blogspot.com/
Organic Synthesis:
The Disconnection Approach
One Group C-C Disconnection of Alcohol and Alkene
Suzuki and Shapiro reaction
The document summarizes the Suzuki and Shapiro reactions. The Suzuki reaction involves a palladium-catalyzed cross-coupling between organoboron compounds and organic halides to form carbon-carbon bonds. It proceeds through oxidative addition, transmetallation, and reductive elimination steps. The Shapiro reaction involves the base-catalyzed decomposition of tosyl hydrazones to form olefins. Both reactions have been used in the synthesis of various drugs and natural products.
Sae 28.8.13
This document discusses the Sharpless epoxidation reaction for asymmetric epoxidation of allylic alcohols. It provides details on the reaction's discovery in 1980, its broad substrate scope and high enantioselectivity. The document also reviews modifications like using molecular sieves or polymer supports, and applications in natural product total syntheses like venustatriol and amphotericin B. Finally, it summarizes other methods for enantioselective epoxidation and recommends the best methods depending on substrate type.
Retrosynthesis
Retrosynthetic analysis is a technique for planning organic syntheses by systematically deconstructing a target molecule into simpler precursor structures through disconnections, with the goal of arriving at commercially available starting materials. Key criteria for good disconnections include a favorable mechanism, maximizing simplification at each step, and producing recognizable starting materials. Common disconnections involve breaking bonds between functional groups like alcohols, alkenes, ketones, acids, and saturated/aromatic hydrocarbons. Protection and activation of reactive groups is sometimes required to control reaction selectivity. Proper application of retrosynthesis allows complex multi-step syntheses to be planned systematically and increases the likelihood of success.
100 named reactions
100 named reactions with examples of total syntheses which utilized these reactions, with reaction conditions. with included references for each syntheses.
organic reaction
The document summarizes two organic reactions: the Dieckmann reaction and ozonolysis reaction. The Dieckmann reaction involves the intramolecular condensation of diesters in the presence of a strong base to form β-keto esters via a 5-exo-trig cyclization. It is used to synthesize cyclopentane and cyclohexane derivatives. Ozonolysis involves the cleavage of unsaturated bonds like alkenes and alkynes with ozone to form carbonyl groups. It can be used to oxidize alkenes into alcohols, aldehydes, ketones or carboxylic acids and is useful for structure elucidation of unknown compounds containing carbon-carbon double bonds.
Lysozyme Enzymology
1. Lysozyme attaches to bacterial cell walls and uses its Glu 35 residue to transfer a proton to cleave the bond between the D- and E-rings of the cell wall, forming an oxonium ion transition state.
2. The Asp 52 carboxylate group then nucleophilically attacks the electron-poor carbon of the D-ring to form a glycosyl-enzyme intermediate.
3. Hydrolysis of this intermediate by Glu 35, forming another transition state, completes the catalytic cycle and releases the D-ring product.
Quinoline
1. Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N. It is colorless and hygroscopic, becoming yellow and brown over time when exposed to light.
2. Quinoline itself has few applications but many derivatives are useful, including quinine which is an important anti-malarial drug. Over 200 biologically active quinoline alkaloids have been identified.
3. The document discusses the structure, properties, synthesis methods like Skraup, Doebner-Miller, and Conrad-Limpach, reactions including electrophilic substitution, oxidation, and reduction, and applications of quinoline and its derivatives in dyes
Organic reaction
This document summarizes several organic reactions including the Mannich reaction, ozonolysis, Mitsunobu reaction, and Baeyer-Villiger oxidation. It provides the mechanisms and synthetic applications of each reaction. The Mannich reaction involves the condensation of an active methyl group in a ketone. Ozonolysis is used to cleave carbon-carbon double bonds and locate their position. The Mitsunobu reaction converts alcohols to other functional groups like esters with inversion of stereochemistry. Baeyer-Villiger oxidation uses a peroxycarboxylic acid to convert a ketone to an ester.
pyrazole ...by saikat hossain....SEU
The document discusses various methods for synthesizing pyrazoles, including the Knorr pyrazole synthesis, reactions involving α,β-unsaturated aldehydes, β-hydroxy ketones, aromatic aldehydes, vinyl ketones, and more. It also covers pharmacological activities of pyrazoles such as antibacterial, antifungal, anticancer, anti-inflammatory, and anti-viral properties. Specific compounds are mentioned that have shown effectiveness against various bacterial, fungal, and viral strains. A wide range of synthetic routes and biological activities of pyrazoles and their derivatives are presented.
Baeyer-Villiger Oxidation
This is a brief introduction to the Baeyer-Villiger Oxidation/Rearrangement in the form of a micro-presentation.
The Baeyer-Villiger Oxidation is useful in the synthesis of esters and lactones. Consult the pdf file for more information.
You are encouraged to visit :
http://www.harinchem.com/named_organic_reactions.html to view a flash micro movie of the mechanism.
Please send feedback or questions through:
http://www.harinchem.com/contactpage.aspx.
The importance of lactone synthesis is underscored by its presence in diverse molecules of pharmacological significance, including statins (HMG CoA reductase inhibitors).
Mannich Reaction
The document discusses various nitrogen substitution and addition reactions including the Mannich reaction where nucleophilic nitrogen adds to saturated or unsaturated carbons. It specifically mentions the reaction of primary amines with aldehydes and ketones to form imines and the formation of amino acids through reactions like the Hell-Volhard Zelensky reaction, Gabriel procedure, nitrosation, and Strecker method.
Important Name reaction
Name reactions:Clemmensen reduction, Darzens condensation, Diels Alder, Eschweiler-Clarke, Friedel-Crafts, Grinard, HofmanMannich, Michael, Meerwin- Pondorf- Verley, Perkin, Reformatsky, Reimer-Tiemann,, Witting and Wolf-Kishner reduction, Aldol condensation.
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This document describes a one-pot, three-component reaction to synthesize densely substituted benzofurans from methyl ketones, phenols, and nucleophiles. Specifically, it details:
1) The reaction of phenylglyoxal monohydrate, phenols like sesamol, and indoles produces benzofurans in good to excellent yields with acid catalysis.
2) Replacing phenylglyoxal with methyl ketones and using I2/DMSO allows an in situ generation of arylglyoxal from the methyl ketone for the reaction.
3) Various substituted benzofurans can be synthesized from different methyl ketones, phenols
Sigmatropic reaction
The document defines and provides examples of various sigmatropic reactions, including:
1. The Claisen rearrangement, which involves the [3,3] rearrangement of an allyl vinyl ether.
2. The Cope rearrangement, which involves the [3,3] sigmatropic rearrangement of 1,5-dienes.
3. The Oxy-Cope rearrangement, which has a hydroxyl substituent and proceeds faster when deprotonated.
4. Other reactions discussed include the Fischer indole synthesis, aromatic Claisen rearrangement, [2,3]-Wittig rearrangement, Carroll rearrangement, and walk rearrangements. Mechanisms
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1. Paracetamol is generally safe at recommended doses but can cause acute liver failure and require transplantation at higher overdose doses due to its intrinsic toxicity.
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Learning new reactions by solving total syntheses merged
- 1. Learning organic reaction mechanisms and new reactions from few total syntheses of molecules. Roshen Reji Idiculla ID MS 14/11 IIRBS
- 2. Enantioselective Total Synthesis of (−)-Pavidolide B; J. Am. Chem. Soc. 2017, 139, 13989−13992 ; DOI: 10.1021/jacs.7b07388 1. Preparation of chiral alcohol from (+)-carvone 2. enantioselective synthesis of formyl cyclopropane
- 4. 3. Mitsunobu reaction of chiral alcohol from (+)-carvone and acid of formyl cyclopropane
- 9. Enantiospecific Total Synthesis of the Highly Strained (−)-Presilphiperfolan-8-ol via a Pd-Catalyzed Tandem Cyclization; DOI: 10.1021/jacs.7b01454 ;
- 14. Protecting Group-Free Total Synthesis of (−)-Lannotinidine B ; dx.doi.org/10.1021/ja305261h | J. Am. Chem. Soc. 2012, 134, 12323−12325 coupling of the α-position of activated alkenes with carbon electrophiles under the catalytic influence of a Lewis base (N-nBu3 or P-nBu3). BrØnsted acid assisted proton transfer step accelerate the reaction, BrØnsted acid remain hydrogen bonded to the resulting enolate in the enantioselectivity determining adol addition step.
- 19. Oxygen-containing proton donors sovent t-BuOH, coordinate to oxophilic SmI2 (but THF coordinates to SmI2, hence in presence of THF, proton donor donot coordinate to SmI2) .
- 21. Total Synthesis of (𝛽)-Cyperolone; 10.1021/ol300058t ; Org. Lett., Vol. 14, No. 5, 2012
- 25. https://www.chem.wisc.edu/areas/reich/syntheses/syntheses.htm 1. Total synthesis of Sterpurenone New: Sahu, R.; Singh, V. J. Org. Chem. 2017, 82, 6268-6278. DOI the HOMO of the diene interacts with LUMO of the dienophile ,so the larger and smaller coefficients can lie side by side respectively. secondary orbital interactions also prefer endo isomer (kinetic product) than exo isomer (thermodynamic product)
- 26. Another analogue of this ketone molecule was created similarly. Then the feasibility of following reactions were confirmed on this molecule.
- 27. So this pathway worked for Next we consider case of But it didn’t give ketal protection ,when keto-ester was treated with ethylene glycol in the presence of p- TsOH . the keto-ester was treated with LiAlH4 to give the diol as result of reduction of both the ketone and ester groups
- 28. BUT THIS bromoketone does not follow cyclization pathway and leads to fragmentation. SO hydroxy-tosylate was converted into the bromo alcohol and subjected to radical cyclization.
- 30. Eupatorium lindleyanum, commonly called is a herbaceous perennial plant in Asteraceae native from China, Japan, Korea and Siberia , which is used as antibacterial or antihistamine agent. . eupalinilide E, isolated from Eupatorium lindleyanum, showed selective cytotoxic activity against A549 cells (lung cancer harboring KRAS mutation). J. Am. Chem. Soc. 2016, 138, 6068−6073 reports an enantioselective synthesis of eupalinilide E accessing >400 mg in a single batch starting from (R)- carvone. - http://www.organic-chemistry.org/namedreactions/yamaguchi-esterification.shtm https://www.synarchive.com/named-reactions/yamaguchi-esterification
- 31. This proposal shows the scheme Synthesis of bicyclic ketone 1st step involves bromination of R-carvone, which acts as a chiral template. Then Favorskii rearrangement of carvone tribromide occurs.
- 32. The cyclic iminolactone is hydrolyzed with aqueous acid to generate lactone.
- 33. use of CeCl3 offers the possibility of coordinates with the other O in ring, which results in a shielding of the frontside of molecule. 4-Methoxybenzyl ether (PMB)
- 37. the addition of vinylmagnesium bromide into lactol formed the incorrect diastereomer which relayed subsequent stereochemistry generated in the synthesis. The formation of the diastereomer, can be rationalized by the chelation controlled addition of vinyl Grignard into the open form alkoxide of lactol . Two changes to the general approach were implemented: delaying the C−H bond oxidation, previously using lactone , until later in the synthesis and installing the 1,1-disubstituted olefin prior to the vinyl addition New procedure
- 38. Previously, the poor yields using Burgess reagent to eliminate the tertiary alcohol prompted the development of a different method for elimination to form olefin
- 39. Trimethylsilylmethylenelactones are Inert to protodesilylation with trifluoroacetic acid or hydroiodic acid.
- 40. This four-step sequence proved cumbersome and made scale-up difficult; as a consequence silicon removal prior to oxidation was achieved by protodesilylation of 42 using trifluoroacetic acid, cleanly yielding triene
- 41. KETONE EPOXIDE