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Title Heterocyclic scaffolds II : reactions and applications of indoles / volume editor, G.W. Gribble ; with contribtions by J.C. Badenock [and others]
Published Berlin : Springer, 2010
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Description 1 online resource (xiii, 488 pages) : illustrations
Series Topics in heterocyclic chemistry, 1861-9282 ; 26
Topics in heterocyclic chemistry ; 26. 1861-9282
Contents Note continued: 1. Introduction -- 2. Dyes and Pigments -- 2.1. Textile Dyes -- 2.2. Dyes for Human Use -- 3. Agriculture -- 4. Animal Health -- 5. Over-the-Counter Drugs -- 5.1. Dietary Supplements -- 5.2. Nutraceuticals -- 6. Essential Oils -- 6.1. Flavor Enhancers -- 6.2. Perfumes -- 7. Summary -- References -- Electrophilic Substitution Reactions of Indoles / Richard J. Sundberg -- 1. Introduction -- 1.1. Experimental Measures of Reactivity -- 1.2. Theoretical Measures of Reactivity -- 1.3. Application of Electrophilic Substitution in Synthesis -- 2. Protonation and Acid-Catalyzed Oligomerization -- 2.1. Equilibrium Protonation -- 2.2. Acid-Catalyzed Oligomerization -- 2.3. Acid-Catalyzed Cyclization -- 2.4. Enzymatic Protonation -- 3. Halogenation and Related Reactions -- 3.1. Fluorination -- 3.2. Chlorination -- 3.3. Bromination -- 3.4. Iodination -- 3.5. Synthetic Applications of 3-Haloindolenine Intermediates -- 3.6. Enzymatic Halogenation -- 3.7. Sulfenylation, Thiocyanation and Cyanation -- 4. Friedel-Crafts Alkylation -- 4.1. Benzylation -- 4.2. Allylation and Prenylation -- 4.3. Alkylation by Electrophilic Alkene Activation -- 4.4. Intramolecular Alkylation -- 5. Alkylation by Carbonyl Compounds -- 5.1. Indol-3-yl Carbinols -- 5.2. Bis-Indolylalkanes and Related Compounds -- 5.3. Tris-Indolylalkanes -- 6. Alkylation by Conjugate Addition -- 6.1. Catalysts for Conjugate Addition -- 6.2. Enantioselective Conjugate Addition to Enones -- 6.3. Reactions with Enediones and Dienones -- 6.4. Reactions with Alkylidene Malonates -- 6.5. Addition with Nitroalkenes -- 6.6. Other Conjugate Addition Reactions -- 6.7. Intramolecular Conjugate Addition -- 6.8. Conjugate Addition with Intramolecular Nucleophilic Capture -- 7. Aminoalkylation (The Mannich Reaction) and Amidoalkylation
Note continued: 7.1. Modified Reaction Conditions -- 7.2. Enantioselective Reaction Conditions -- 7.3. Intramolecular Aminoalkylation: The Pictet-Spengler Reaction -- 7.4. Bischler-Napieralski Reaction -- 8. Acylation -- 8.1. C-3 Acylation -- 8.2. C-Ring Acylation -- 8.3. Intramolecular Acylation -- References -- Reactions of Indole with Nucleophiles / Tara L.S. Kishbaugh -- 1. Introduction -- 2. Nucleophilic Additions to Indoles -- 2.1. Nucleophilic Additions to Nitroindoles -- 2.2. Nucleophilic Additions to & alpha;, & beta;-Unsaturated Nitrones -- 2.3. Pummerer Reactions to Create Spiro-Indolenines -- 2.4. Addition of Carbon Nucleophiles to Alkylideneindolium Ions -- 2.5. Pyridoindole-Based Quinone Methides -- 3. Nucleophilic Substitution Reactions of Indole -- 3.1. Vicarious Nucleophilic Substitutions -- 3.2. Ipso Substitution -- 3.3. SN2' -- References -- Metalation of Indole / Erin T. Pelkey -- 1. Introduction -- 2. Metalation Directed by Nitrogen Functionality -- 2.1. C2-Lithiation of N-Methylindoles -- 2.2. C2-Lithiation of N-(Arylsulfonyl)indoles -- 2.3. C2-Lithiation of N-(Carboalkoxy)indoles -- 2.4. C2-Lithiation of Indole-1-Carboxylic Acids -- 2.5. C2-Lithiation of Other N-(Substituted)indoles -- 2.6. C2 Metalation with Other Metals -- 2.7. C3-Lithiation -- Metal-Catalyzed Cross-Coupling Reactions for Indoles / Gordon W. Gribble -- 1. Introduction -- 2. Palladium-Catalyzed Cross-Coupling Reactions -- 2.1. Mori-Ban Indole Synthesis -- 2.2. Larock Indole Synthesis -- 2.3. Oxidative Coupling -- 2.4. Kumada Coupling -- 2.5. Negishi Coupling -- 2.6. Suzuki Coupling -- 2.7. Stille Coupling -- 2.8. Sonogashira Coupling -- 2.9. Heck Coupling -- 2.10. Carbonylation -- 2.11. C-N Bond Formation -- 2.12. Direct Arylation -- 3. Copper-Catalyzed Cross-Coupling Reactions -- 3.1. Selective N1-Arylation
Note continued: 3.2. Selective C2-Arylation -- 3.3. Selective C3-Arylation -- 4. Rhodium-Catalyzed Cross-Coupling Reactions -- 4.1. Selective C2-Arylation -- 4.2. Selective C3-Arylation -- 5. Iron-Catalyzed Cross-Coupling Reactions -- 6. Nickel-Catalyzed Cross-Coupling Reactions -- References -- Radical Reactions of Indole / Jeanese C. Badenock -- 1. Introduction -- 2. Intermolecular Radical Reactions -- 2.1. Radical Addition and Substitution Reactions of Indole -- 2.2. Radical Addition Reactions of Indolylacyl Radicals -- 3. Intramolecular Radical Reactions -- 3.1. Synthesis of the Indole Core -- 3.2. Synthesis of Spirooxindoles and Spiroindolines -- 3.3. Synthesis of Indole-Fused Five-Membered and Six-Membered Rings -- 3.4. Synthesis of Indole-Fused Seven-Membered and Eight-Membered Rings -- References -- [2+2], [3+2] and [2+2+2] Cycloaddition Reactions of Indole Derivatives / Steven J. Berthel -- 1. Introduction -- 2. [2+2] Cycloadditions -- 2.1. [2+2] Cycloadditions Between Indole Aryne Molecules and Olefins -- 2.2. [2+2] Photocycloaddition of Indoles and Olefins -- 2.3. [2+2] Cycloadditions of Indoles and Alkynes -- 2.4. [2+2] Cycloadditions of Indoles and Carbonyl Groups -- 3. Indole 2,3-Dipolar Cycloadditions -- 3.1. Indole Pyrrole Ring as Dipolarophile -- 3.2. Indole Phenyl Ring as Dipolarophile -- 3.3. Indole Pyrrole Ring as Dipole -- 4. [2+2+2] Cycloadditions -- 5. Conclusion -- References -- [4+2] Cycloaddition Reactions of Indole Derivatives / Fariborz Firooznia -- 1. Introduction -- 2. Indoles as Dienophiles in [4+2] Cycloaddition Reactions -- 2.1. Inverse Electron Demand Diels-Alder Reactions with Azadienes -- 2.2. Inverse Electron Demand Diels-Alder Reactions with Other Dienes -- 2.3. Inverse Electron Demand Diels-Alder Reactions in the Synthesis of Natural Products
Note continued: 2.4. Indoles as Dienophiles in "Normal" Electron Demand Diels-Alder Reactions -- 2.5. Cycloadditions Involving Indole Aryne Derivatives or Double Bonds in the Benzoid Portion of the Indole -- 3. Indole as Diene: 2-Vinylindoles -- 3.1. General Considerations: Regio and Stereochemistry -- 3.2. Application of [4+2] Reactions with 2-Vinylindoles to the Synthesis of "Linear" Indole Alkaloids -- 3.3. Application of [4+2] Reactions with 2-Vinylindoles to the Synthesis of Pyrrolo and Indolocarbazoles -- 3.4. Application of [4+2] Reactions with 2-Vinylindoles to the Synthesis of Vinca Alkaloids -- 3.5. 2-Alkynyl Indoles and 2-Allenylindoles as Dienes in Cycloaddition Reactions -- 4. Indole as Diene: 3-Vinylindoles -- 4.1. Simple 3-Vinylindole Systems -- 4.2. Application of Diels-Alder Reactions with 3-Vinylindoles in the Synthesis of Biscarbazoles -- 4.3. 3-Quinone-Indole Systems as Dienes -- 4.4. Application of Diels-Alder Reactions with 3-Vinylindoles in the Synthesis of Novel Pentacyclic Systems -- 4.5. Application of Diels-Alder Reactions with 3-Vinylindoles in the Synthesis of Indolocarbazoles and Pyrrolocarbazoles -- 4.6. Application of Diels-Alder Reactions with 3-Vinylindoles in the Synthesis of & beta; and & gamma;-Carboline Alkaloids -- 4.7. Tandem Reactions and Multicomponent Syntheses -- 5. Indoles as Dienes: Noncyclic Indolo-2,3-quinodimethanes -- 5.1. Indolo-2,3-quinodimethanes from Bis(bromomethyl)indoles -- 5.2. Indolo-2,3-quinodimethanes from Gramine Derivatives -- 5.3. In Situ Generated Indolo-2,3-dienolates as Indolo-2,3-quinodimethanes -- 5.4. Indolo-2,3-quinodimethanes from 3-Cyanomethyl-2-vinylindoles -- 5.5. Indolo-2,3-quinodimethanes from Intramolecular Heck Reactions of & alpha;-Phosphono Enecarbamates -- 5.6. Indolo-2,3-quinodimethanes from Intramolecular Heck Reactions of & alpha;-Phosphono Enecarbamates
Note continued: 5.7. Multicomponent Synthesis with Indolo-2,3-quinodimethanes -- 6. Indoles as Dienes: Fused Cyclic Indolo-2,3-quinodimethanes -- 6.1. Furo[3,4-b]indoles as Indolo-2,3-quinodimethanes Analogs -- 6.2. Pyrrolo[3,4-b]indoles as Indolo-2,3-quinodimethanes Analogs -- 6.3. Pyrano[3,4-b]indolones as Indolo-2,3-quinodimethanes Analogs -- 6.4. Indolo-3-sulfolenes as Indolo-2,3-quinodimethanes Analogs -- 6.5. Indolo-4,5-quinodimethane Analogs -- 7. Conclusion -- References -- Oxindoles and Spirocyclic Variations: Strategies for C3 Functionalization / Jonathon S. Russel -- 1. Introduction -- 2. Methods for Quaternization at Oxindole C3 -- 2.1. Construction of All-Carbon Quaternary Centers -- 2.2. Construction of Heteroatom Containing C3 Quaternary Centers -- 3. Methods for Spirocyclization at Oxindole C3 -- 3.1. Synthesis of All-Carbon C3 Spirocenters -- 3.2. Synthesis of Heteroatom Containing C3 Spirocycles -- 4. Natural Product Total Synthesis -- 4.1. Oxindole Intermediates in Natural Product Synthesis -- 4.2. Oxindole Natural Product Total Synthesis -- 5. Concluding Remarks -- References -- Advances in the Total Syntheses of Complex Indole Natural Products / Liangfeng Fu -- 1. Introduction -- 2. Indole Alkaloids with Potent Biological Activity -- 2.1. Actinophyllic Acid -- 2.2. Communesin F and Perophoramidine -- 2.3. Diazonamide A -- 2.4. Minfiensine -- 2.5. Stephacidin B -- 2.6. Yatakemycin -- 3. Other Complex Indole Alkaloids -- 3.1. Chartelline C -- 3.2. Haplophytine -- 3.3. Kapakahine B -- 3.4. ( -- )-Penitrem D -- 3.5. Phalarine -- 3.6. Quadrigemine C and 11,11'-Dideoxyvertillin A -- 3.7. Welwitindolinone A -- References
Summary Yong-Jin Wu New Indole-Containing Medicinal Compounds Timothy C. Barden Indoles: Industrial, Agricultural and Over-the-Counter Uses Richard J. Sundberg Electrophilic Substitution Reactions of Indoles Tara L.S. Kishbaugh Reactions of Indole with Nucleophiles Erin Pelkey Metalation of Indole Jie Jack Li · Gordon W. Gribble Metal-Catalyzed Cross-Coupling Reactions for Indoles Jeanese C. Badenock Radical Reactions of Indole Fariborz Firooznia · Robert F. Kester · Steven J. Berthel [2+2], [3+2] and [2+2+2] Cycloaddition Reactions of Indole Derivatives Steven J. Berthel · Fariborz Firooznia · Robert F. Kester [4+2] Cycloaddition Reactions of Indole Derivatives Jonathon S. Russel Oxindoles and Spirocyclic Variations: Strategies for C3 Functionalization Liangfeng Fu Advances in the Total Syntheses of Complex Indole Natural Products
Bibliography Includes bibliographical references and index
Notes Print version record
Subject Indole.
Form Electronic book
Author Gribble, Gordon W.
Badenock, J. C. (Jeanese C.)
LC no. 2010927759
ISBN 3642157335
9783642157332