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Format: 1 online resource (340 p.)

ISBN: 0-12-804845-X , 0-12-804695-3

Series Statement: Advances in Heterocyclic Chemistry, Volume 119

Note: Description based upon print version of record. , Front Cover -- Advances in Heterocyclic Chemistry -- EDITORIAL ADVISORY BOARD -- Advances in Heterocyclic Chemistry Heterocyclic Chemistry in the 21st Century: A Tribute to Alan Katritzky -- Copyright -- Contents -- CONTRIBUTORS -- PREFACE -- One - The Benzotriazole Story -- 1. 1H-BENZOTRIAZOLE AS A SYNTHETIC TOOL -- 2. 1H-BENZOTRIAZOLE IN THE SYNTHESIS OF HETEROCYCLES -- 3. ACYLATION, AROYLATION, AND HETEROAROYLATION BY BT TECHNOLOGY -- 4. ALKYLATIONS, HETEROALKYLATIONS, AND BT-STABILIZED CARBANIONS -- 4.1 Alkylations and Heteroalkylations -- 4.2 Bt-Stabilized Carbanions -- 5. REARRANGEMENTS OF BENZOTRIAZOLE DERIVATIVES -- 6. BENZOTRIAZOLE IN THE SYNTHESIS OF PEPTIDES AND ISOPEPTIDES -- 7. BENZOTRIAZOLE IN THE SYNTHESIS OF AMINO ACID/PEPTIDE BIOCONJUGATES -- 8. NATIVE CHEMICAL LIGATION USING BENZOTRIAZOLE CHEMISTRY -- 9. BENZOTRIAZOLE IN THE SYNTHESIS OF CYCLIC PEPTIDES AND CYCLIC PEPTIDOMIMETICS -- 10. BENZOTRIAZOLE IN THE SYNTHESIS OF PEPTIDOMIMETICS -- 11. CONCLUSION -- REFERENCES -- Two - Flow Synthesis of Heterocycles -- 1. INTRODUCTION -- 2. CURRENT CHALLENGES -- 2.1 Dealing with Solids -- 3. DEVELOPING FIELDS -- 3.1 Catalysis -- 3.1.1 Enzymatic Reactions -- 3.1.2 Heterogeneous Catalysis -- 3.2 Photochemistry -- 3.3 Electrochemistry -- 3.4 Tube-In-Tube Reactors -- 4. TELESCOPING -- 4.1 In-line Purification -- 4.1.1 Solid Phase-Bound Scavenging Protocol -- 4.1.2 Continuous Separation -- 4.1.3 Distillation -- 4.1.4 Crystallization -- 4.2 Online Analysis and Automation -- 4.3 Lab-On-A-Chip -- 5. CONCLUSION -- REFERENCES -- Three - Hypervalent Heterocycles -- 1. INTRODUCTION -- 2. GENERAL OVERVIEW OF HYPERVALENT COMPOUNDS -- 3. HYPERVALENT HETEROCYCLIC COMPOUNDS OF GROUP 13 ELEMENTS -- 3.1 Hypervalent Boron Heterocycles -- 3.2 Hypervalent Aluminum -- 4. HYPERVALENT HETEROCYCLIC COMPOUNDS OF GROUP 14 ELEMENTS. , 4.1 Hypervalent Silicon Heterocycles -- 4.2 Hypervalent Germanium, Tin, and Lead -- 5. HYPERVALENT HETEROCYCLIC COMPOUNDS OF GROUP 15 ELEMENTS -- 5.1 Hypervalent Phosphorus Heterocycles -- 5.2 Hypervalent Arsenic, Antimony, and Bismuth -- 6. HYPERVALENT HETEROCYCLIC COMPOUNDS OF GROUP 16 ELEMENTS -- 6.1 Hypervalent Sulfur Heterocycles -- 6.2 Hypervalent Selenium and Tellurium -- 7. HYPERVALENT HETEROCYCLIC COMPOUNDS OF GROUP 17 ELEMENTS -- 7.1 Hypervalent Bromine(III) Heterocycles -- 7.2 Hypervalent Iodine(III) Heterocycles -- 7.2 Hypervalent Iodine(V) Heterocycles -- REFERENCES -- Four - Natural Products Containing Nitrogen Heterocycles-Some Highlights 1990-2015 -- 1. INTRODUCTION -- 2. ISOLATION, STRUCTURE DETERMINATION, AND BIOSYNTHESIS -- 3. STRUCTURES -- 4. SYNTHESES -- 5. SUMMARY -- REFERENCES -- Five - Natural Products Containing Oxygen Heterocycles-Synthetic Advances Between 1990 and 2015 -- 1. INTRODUCTION -- 2. FORMATION OF A C-O BOND -- 2.1 1,4-Conjugate Addition -- 2.1.1 Five- and Six-Membered Rings -- 2.1.2 Spiroketals -- 2.1.3 Seven-Membered Rings -- 2.2 Metal-Induced Cyclization -- 2.2.1 Five-Membered Rings -- 2.2.2 Six-Membered Rings -- 2.2.3 Spiroketals -- 2.2.4 Medium-Ring Size (7- to 10-Membered Rings) -- 2.2.5 Macrocycles (12- to 16-Membered Rings and More) -- 2.3 Intramolecular Nucleophilic Ring-Opening of Epoxides -- 2.3.1 Five-Membered Rings to Medium-Ring Size -- 3. FORMATION OF A C-C BOND -- 3.1 Metathesis -- 3.1.1 Five-Membered Rings -- 3.1.2 Six-Membered Rings (Tetrahydropyrans and Lactones) -- 3.1.3 Spiroketals -- 3.1.4 Medium-Sized Cyclic Ethers (7- to 10-Membered Rings) -- 3.1.5 Macrocycles -- 3.2 Nucleophilic Addition to Acetals and Hemiacetals-C2 Functionalization of Lactol -- 3.3 Prins-Type Reaction -- 3.3.1 Five-Membered Rings -- 3.3.2 Six-Membered Rings -- 3.3.3 Medium-Sized Rings -- 3.4 Cycloaddition/Annulation. , 3.4.1 Five-Membered Rings -- 3.4.2 Six-Membered Rings -- 3.4.3 Spiroketals -- 3.4.4 Large Rings -- 4. CONCLUSION -- REFERENCES -- Six - N-Heterocyclic Carbenes -- 1. INTRODUCTION -- 2. FROM HISTORY TO MODERN SYNTHESES OF N-HETEROCYCLIC CARBENES -- 2.1 Decarboxylations and Extrusions of Other Heterocumulenes from Mesomeric Betaines -- 2.2 Deprotonations of Hetarenium Salts -- 2.3 α-Eliminations -- 2.4 N-Heterocyclic Carbenes by Tautomerizations of Mesomeric Betaines -- 2.5 Desulfurizations -- 3. SELECTED EXAMPLES OF N-HETEROCYCLIC CARBENES AND RELATIVES -- 3.1 Acyclic Diamino Carbenes -- 3.2 Three-Membered N-Heterocyclic Carbenes -- 3.3 Four-Membered N-Heterocyclic Carbenes -- 3.4 Five-Membered N-Heterocyclic Carbenes -- 3.5 Six-Membered N-Heterocyclic Carbenes -- 3.6 Anionic N-Heterocyclic Carbenes of Five- and Six-Membered N-Heterocyclic Carbenes -- 3.7 Seven- and Eight-Membered N-Heterocyclic Carbenes -- 4. CONCLUSIONS -- REFERENCES -- Seven - Stable N- and N/S-Rich Heterocyclic Radicals: Synthesis and Applications -- 1. INTRODUCTION -- 2. SYNTHESIS AND CHEMISTRY OF NITROGEN-BASED HETEROCYCLIC RADICALS -- 2.1 Nitrogen-Centered Heterocyclic Radicals -- 2.1.1 Verdazyls -- 2.1.1.1 C3-Saturated Verdazyls -- 2.1.1.2 3(2H)-Oxo- and Thiooxoverdazyls -- 2.1.2 Benzo[e][1,2,4]triazinyls -- 2.2 Sulfur/Nitrogen-Centered Heterocyclic Radicals-Thiazyls -- 2.2.1 Cyclic Thioaminyls and 1,2,4-Benzothiadiazinyls -- 2.2.2 1,2,3-Dithiazolyls -- 2.2.3 1,3,2-Dithiazolyls -- 2.2.4 1,2,3,5- and 1,3,2,4-Dithiadiazolyls -- 2.2.5 1,2,4,6-Thiatriazinyls -- 3. APPLICATIONS -- 4. CONCLUDING REMARKS -- REFERENCES -- Eight - New Developments in Heterocyclic Tautomerism: Desmotropes, Carbenes and Betaines -- 1. INTRODUCTION: DESMOTROPES, TAUTOMERS, AND POLYMORPHS -- 2. TECHNIQUES USED FOR DESMOTROPY STUDIES -- 3. EXAMPLES OF DESMOTROPY. , 3.1 Desmotropy of Hydantoins, Thiohydantoins, and Thiohydantoin Anions -- 3.1.1 Hydantoins and Thiohydantoins -- 3.1.2 Thiohydantoin Anions -- 3.2 Desmotropy of Imidazolinones and 1(3H)-Imidazole-5(4)-carboxamide -- 3.2.1 Imidazolinones -- 3.2.2 4(5)-Amino-1(3)H-imidazole-5(4)-carboxamide -- 3.3 Desmotropy of Pyrazoles -- 3.3.1 3(5)-Phenyl-1H-pyrazole -- 3.3.2 3(5)-Phenyl-5(3)-methylpyrazole -- 3.3.3 4-Acylpyrazolin-5-ones -- 3.3.4 1H-4-Nitropyrazoles -- 3.4 Desmotropy of 3-Phenylindazole -- 3.5 Desmotropy of Dimethyl (3-Methylthio-1,2,4-triazol-5-yl)iminodithiocarbonate -- 3.6 Desmotropy of Rhodanine -- 3.7 Desmotropy of 2-Amidobenzothiazoles -- 3.8 Desmotropy of N-Pyridylpyrrolinones -- 3.9 Desmotropy of 2-(2′,4′-Dinitrobenzyl)-3-methylpyridine -- 3.10 Desmotropy of Aminoquinolines -- 3.11 Desmotropy of Schiff Bases -- 3.12 Desmotropy of 2-Amino-3-hydroxy-6-phenylazopyridine -- 3.13 Desmotropy of Barbituric and Thiobarbituric Acid -- 3.13.1 Barbituric Acid -- 3.13.2 2-Thiobarbituric Acid -- 3.14 Desmotropy of 2,6-Dichloropurine -- 3.15 Desmotropy of 3-Ethoxycarbonyl-2-phenyl-4,1-benzothiazepine and Its Derivatives -- 4. DESMOTROPY OF PHARMACEUTICALLY IMPORTANT COMPOUNDS -- 4.1 Desmotropy of the Schiff Base of Diethylaminomalonate and Pyridoxal Hydrochloride -- 4.2 Desmotropy of Irbesartan (A Tetrazole Derivative) -- 4.3 Desmotropes of Albendazole -- 4.4 Desmotropy of Omeprazole and Esomeprazole -- 4.5 Desmotropy of Pyroxicam -- 4.6 Desmotropy of Sulfasalazine -- 4.7 Co-crystals of Gentisic Acid with Pyridine Derivatives -- 5. TAUTOMERISM OF CARBENES AND BETAINES -- 5.1 The Relationship between N-Heterocyclic Carbenes and Heterocyclic Mesomeric Betaines -- 5.2 Theoretical Studies of Pyridine-Derived N-Heterocyclic Carbenes -- 5.3 Tautomeric Equilibrium of Mesoionic Compounds with a Normal N-Heterocyclic Carbene. , 5.4 Tautomeric Equilibrium between Ylides and N-Heterocyclic Carbenes -- REFERENCES -- Nine - Recent Advances of 1,3-Dipolar Cycloaddition Chemistry for Alkaloid Synthesisa -- 1. INTRODUCTION -- 2. CARBONYL YLIDES -- 3. MESOIONIC SYSTEMS -- 4. AZIDES -- 5. AZOMETHINE YLIDES -- 6. AZOMETHINE IMINES -- 7. NITRONES -- 8. NITRILE OXIDES -- 9. ASYMMETRIC REACTIONS OF 1,3-DIPOLES -- 10. CONCLUDING REMARKS -- ACKNOWLEDGMENT -- REFERENCES -- INDEX -- A -- B -- C -- D -- E -- F -- G -- H -- I -- J -- K -- L -- M -- N -- O -- P -- Q -- R -- S -- T -- V -- U -- W -- X -- Y -- Z -- Back Cover.

Language: English