More Synthetic Approaches to Nonaromatic Nitrogen Heterocycles, 2 Volume Set

More Synthetic Approaches to Nonaromatic Nitrogen Heterocycles An authoritative collection of resources discussing the latest trends in the synthesis of nonaromatic nitrogen heterocycles Widely distributed in nature, nitrogen heterocycles are extremely common in synthetic substances found in pharmaceuticals, agrochemicals, and materials. The literature is evolving rapidly and explores newly emerging structures and medicines. More Synthetic Approaches to Nonaromatic Nitrogen Heterocycles offers R&D professionals the opportunity to easily access a collection of the latest relevant research in the area. In the second two-volume set of this practical reference distinguished researcher Dr. Ana Maria M. M. Faisca Phillips delivers a collection of resources focusing on the newest and most widely applicable trends emerging in synthetic strategies for nonaromatic nitrogen heterocycles. With coverage of topics including organocatalysis, cascade reactions, flow chemistry in synthesis, cycloaddition reactions, metathesis, cross-coupling reactions, and electrochemistry, the book provides quick access to critical new avenues of synthesis. More Synthetic Approaches to Nonaromatic Nitrogen Heterocycles: Volume 1 and 2 also offers readers: A thorough introduction to recent advances in the design and synthesis of cyclic peptidomimetics Comprehensive explorations of fused heterocycles and transition metal promoted synthesis of isoindoline derivatives Practical discussions of 1,4-diazepane ring-based systems and recent advances in the synthesis of azepane-based compounds In-depth examinations of strained aziridinium ions, asymmetric organocatalysis in alternative media, and the electrochemical synthesis of non-aromatic N-heterocycles Perfect for academic and industrial researchers in organic chemistry and synthesis, organometallic chemistry, pharmaceutical chemistry catalysis, and sustainable chemistry, More Synthetic Approaches to Nonaromatic Nitrogen Heterocycles: Volume 1 and 2 is an indispensable reference for anyone seeking an authoritative source of information on new and emerging trends in synthesis.

List of Contributors Preface List of Common Abbreviations   PART 1: CASCADE REACTIONS   1             Unity is Strength: The Case of Cascade Reactions Combined with C–H Activation  1                Emanuele  Casali, Ervis Saraci and Giuseppe Zanoni                1.1         Introduction 1.2         Rhodium Promoted Reactions 1.3         Palladium Promoted Reactions 1.4         Ruthenium Promoted Reactions 1.5         Cobalt Promoted Reactions 1.6         Miscellaneous References   2             Chemo-enzymatic Cascade Reactions for the Synthesis of Chiral Intermediates                and Nonaromatic Nitrogen Heterocycles Rodrigo O.M.A. de Souza, Raquel A.C. Leão, Marcelo A. Nascimento, Alexandre de S. França, Amanda S. de Miranda, Ivaldo I. Junior   2.1         Introduction 2.2         C–N Bond Construction Enzymes 2.3         C–N Deracemization Enzymes 2.4         Cascade Reactions 2.4.1      Enzymatic Cascade Reactions 2.4.2      Chemoenzymatic Cascade Reactions References   3             Asymmetric Organocatalytic Cascade Reactions for the Synthesis of Nitrogen Heterocycles A. M. M. M. Faisca Phillips   3.1 Introduction 3.2 Three-membered Ring Heterocycles: Aziridines 3.3 Four-membered Ring Heterocycles: The β-lactams 3.4 Five-membered Rings 3.4.1 Pyrrolidines 3.4.2 Pyrrolidinones (-Lactams) 3.4.3 Isoindolinones and Spirooxindoles 3.5 Six-membered Rings 3.5.1 Piperidines, Dihydropyridines and Tetrahydropyridines 3.5.2 Piperidinones (-lactams) 3.5.3 Dihydropyridinones 3.5.4 Tetrahydroquinolines, Dihydroquinolines and Related Substances 3.5.5 Hexahydropyridazines and Pyrimidinones 3.6 Pyrrolo[3,2,1-ij]quinolines 3.7 Cyclic Sulfamidates 3.8 Miscellaneous Conclusion References     PART 2: SELECTED REACTIONS FOR THE SYNTHESIS OF NITROGEN HETEROCYCLES   4             Synthesis of Nitrogen-Heterocycles Based on N-Heterocyclic Carbene Organocatalysis                Hideto Miyabe                  4.1         Introduction 4.2         NHC-catalyzed Cyclization 4.3         NHC-catalyzed Annulation 4.3.1      [3 + 2] Annulation 4.3.2      [4 + 2] Annulation 4.3.3      [3 + 3] Annulation 4.3.4      [4 + 3] Annulation 4.3.5      [2 + 2] Annulation 4.4         Oxidative NHC-catalyzed Annulation 4.4.1      Oxidative [3 + 2] Annulation 4.4.2      Oxidative [4 + 2] Annulation 4.4.3      Oxidative [3 + 3] Annulation 4.4.4      Oxidative [4 + 3] Annulation 4.4.5      Oxidative [2 + 2] Annulation 4.5         Asymmetric Dearomatization 4.6         Cooperative Catalysis of NHC and Transition-Metal Catalysts 4.7         Other NHC-catalyzed Reactions 4.8         Conclusion and Outlook References   5             Synthesis of N-Heterocycles via [3 + n] Cycloaddition Reactions of Vinyl Metal Carbene Intermediates                Ming Bao, Su Zhou, and Xinfang Xu                  5.1         Introduction 5.2         [3 + 1]-Cycloaddition 5.3         [3 + 2]-Cycloaddition 5.4         [3 + 3]-Cycloaddition 5.4.1      [3 + 3]-Cycloaddition with Nitrone 5.4.2      [3 + 3]-Cycloaddition with Azomethine Imines 5.4.3      [3 + 3]-Cycloaddition with Other 1,3-Dipoles 5.5         [3 + 4]-Cycloaddition 5.5.1      [3 + 4]-Cycloaddition with N-Heterocycles 5.5.2      [3 + 4]-Cycloaddition with α,-Unsaturated Imines 5.5.        Other Types of [3 + 4]-Cycloadditions 5.6         [3 + 5]-Cycloaddition 5.7         Intramolecular Cyclization via Carbene/Alkyne Metathesis Process 5.8         Summary and Outlook References   6             Recent Progress in the Synthesis of Amine-containing Heterocycles by Metathesis Reactions                Zeyue Zhang, Damien Hazelard, and Philippe Compain                  6.1         Introduction 6.2         Five-membered Cyclic Amines 6.3         Six-membered Cyclic Amines 6.3.1      Natural Products and Related Compounds 6.3.2      Sugar Mimetics 6.3.3      RCM of Phenylamines and Related Analogues 6.3.4      Miscellaneous 6.4         Seven-membered to Macrocyclic Amines 6.5         Tandem Reactions 6.6         Conclusion References   7             Metal-Catalyzed Synthesis of N-Heterocycles Via Borrowing-Hydrogen Annulation                A. Sofia Santos, Daniel Raydan, Nuno Viduedo, M. Manuel B. Marques, and Beatriz Royo   7.1         Introduction 7.2         Metal-Catalyzed Borrowing Hydrogen Annulation Reactions 7.2.1      Rh-Catalyzed Borrowing Hydrogen Reactions 7.2.2      Ru-Catalyzed Borrowing Hydrogen Reactions 7.2.3      Ir-Catalyzed Borrowing Hydrogen Reactions 7.2.4      Fe-Catalyzed Borrowing Hydrogen Reactions 7.2.5      Ni-Catalyzed Borrowing Hydrogen Reactions 7.3         Conclusions References   8             Synthesis of N-Heterocycles Via Metal-Catalyzed Intramolecular Buchwald-Hartwig C-N Cross Coupling Reactions                Auxiliadora Prieto   8.1         Introduction 8.2.        Applications of Intramolecular Pd-Catalyzed N-Arylation of amine in the Synthesis of Nonaromatic Heterocycles. 8.2.1.     Synthesis of Five-membered N-Heterocycles. 8.2.2.     Synthesis of Six-membered N-Heterocycles. 8.2.3.     Applications in the Synthesis of both Five- and Six-membered N-Heterocycles 8.2.4.     Synthesis of Seven-membered N-Heterocycles 8.3.        Applications of Intramolecular Pd-Catalyzed N-arylation of amide in the Synthesis of Nonaromatic Heterocycles. 8.3.1.     Applications in the Synthesis of Five-membered N-Heterocycles. 8.3.2.     Application in the Synthesis of Six-membered N-Heterocycles 8.3.3.     Application in the Synthesis of Seven-membered N-Heterocycles 8.4.        Intramolecular Pd-Catalyzed Arylation of Sulfonamides. 8.5         Applications of the Intramolecular Buchwald-Hartwig Amination in the Synthesis of Natural Products. 8.6         Conclusion References   9             Synthesis of Nonaromatic Nitrogen Heterocycles Via Singlet Oxygen                João Tomé, Kelly A.D.F. Castro, Leandro M. O. Lourenço, Roberto Santana Da Silva,                  9.1         Introduction 9.2         Singlet Oxygen on Organic Synthesis 9.2.1      Oxidation of Bipyrroles 9.2.2      Synthesis of (R)-methylnaltrexone 9.2.3      Synthesis of Glochidine and Glochidicine 9.2.4      Synthesis of γ-lactams via One-pot Synthesis 9.2.5      Synthesis of the Melohenine B 9.2.6      Synthesis of Pyrrolidine Derivatives by [2 + 3] Cycloaddition, via 1O2 Mediated 1,3-dipole 9.2.7      Synthesis of Pandamarine 9.2.8      Preparation of Bicyclic Lactam 9.2.9      Synthesis of Alkaloids 9.2.10   Synthesis of Azaspiro Frameworks 9.2.11 Preparation of Tetrahydropyranopyrrolones 9.2.12 Synthesis of 2-oxindoles 9.2.13 Synthesis of Several Natural Products from an Amino Furan Derivative 9.2.14 Synthesis of Peptide-fluorescent Probes 9.2.15 Synthesis of Tetrahydroquinoline 9.3         Conclusion References   10           Cobalt-catalysed Carbonylation for the Synthesis of N-Heterocyclic Compounds                Anup Paul and Armando J.L. Pombeiro                  1.            Introduction 2.            Cobalt-catalysed Carbonylation for the Synthesis of N-heterocyclic Compounds Using CO Gas as CO source 3.            Cobalt-catalysed Carbonylation for the Snthesis of N-heterocycles Using CO Surrogates 4.            Conclusions References   11           Enantioselective Synthesis of Nitrogen Heterocycles Using Chiral Hypervalent Iodine Reagents                Ana Maria Faisca Phillips and Armando J.L. Pombeiro   11.1       Introduction 11.2       The Historical Development of Chiral Hypervalent Iodine Reagents 11.3       Synthesis with Chiral Hypervalent Iodine Reagents 11.3.1   Difunctionalization of Alkenes 11.3.2   Dearomatization Reactions 11.3.3   α-Functionalization of Carbonyl Compounds 11.4       Conclusion References   PART III. SPECIAL TECHNIQUES   12           Continuous Flow Chemistry                Marcus Baumann                  12.1       Introduction To Modern Flow Chemistry 12.2       Value of Heterocyclic Chemistry for Modern Drug Discovery Programs 12.3       Case Studies of Flow Chemistry Applied to Heterocyclic Targets 12.3.1    Flow Synthesis of Three-membered Saturated Heterocycles 12.3.2    Flow Synthesis of Four-membered Saturated Heterocycles 12.3.3    Flow Synthesis of Five-membered Saturated Heterocycles 12.3.4    Flow Synthesis of Six-membered Saturated Heterocycles 12.3.5    Flow Synthesis of Seven-membered Saturated Heterocycles 12.3.6    Flow Synthesis of Macrocyclic Saturated Heterocycles 12.4       Assessment of the Merits of Continuous Flow Processing for Heterocycle Synthesis 12.5       Summary and Conclusions References   13           The Electrochemical Synthesis of Non-Aromatic N-Heterocycles Oana R. Luca   13.1       Introduction 13.2       Laws of Organic Electrosynthesis 13.2.1    Types of Electrolyses 13.2.2    Diagnostic Analytical Methods: Voltammetry 13.3.      Construction of Three- and Four Membered Non-Aromatic Heterocycles 13.3.1 Aziridines 13.3.2 Epoxides 13.3.3 Azetidines 13.4       Construction of Five Six and Seven Membered Non-Aromatic Heterocycles 13.4.1   Pyrrolidines 13.4.2   Indolines and dihydrobenzofurans 13.4.3   Pyrrolidinones, 5-membered Cyclic Carbamates and Derivatives 13.4.4   Tetrahydrooxazole and Tetrahydrooxazine Derivatives 13.4.5   6-membered Amides, Carbamates, and Derivatives 13.5       Construction of Nonaromatic Heterocycles with Fused Polycyclic Systems 13.5.1   Nonaromatic Heterocycles from Phtalimides and Succinimides 13.5.2   Polyciclic Peptides 13.5.3   Polyclic Ureas 13.5.5   Ring-fused Quinones Conclusion References   14          Asymmetric Organocatalysis in Alternative Media                Luis C. Branco, Verônica Diniz, Karolina Zalewska, and Miguel M. Santos                  14.1       Introduction 14.2       Water as Reaction Medium 14.3       Ionic Liquids as Alternative Media 14.4       Miscellaneous Alternative Reaction Media 14.5       Conclusions References   PART IV. SYNTHETIC METHODS FOR SPECIAL COMPOUND CLASSES   15           The Strained Aziridinium Ion                Jala Ranjith and Hyun-Joon Ha                  15.1       Introduction 15.2       Formation of Aziridinium Ions 15.3       Ring Opening of Aziridinium Ion 15.4       Synthetic Applications 15.5       Bicyclic Aziridinium Ion and its Application Ackowledgments References   16           Recent advances on the synthesis of azepane-based compounds                Maria Assunta Chiacchio, Laura Legnani, Ugo Chiacchio, and Daniela Iannazzo   16.1       Introduction 16.2       Azepane Synthesis 16.2.1    Synthesis of Substituted Azepanes 16.2.2 Synthesis of Ring-fused Azepanes 16.2.3 Synthesis of Azepane-based Alkaloids Conclusion                 17           1,4-Diazepane Ring-based Systems                Eduarda M.P. Silva, Pedro A.M.M. Varandas, and Artur M.S. Silva   17.1       Introduction 17.2       Reductive Amination 17.3       Mitsunobu Amination 17.4       1,3-Dipolar Cycloaddition 17.5       Multicomponent Reactions 17.6       Other Methods Conclusions References   18           Transition Metal Promoted Synthesis of Isoindoline Derivatives                Laura A. Aronica and Gianluigi Albano   18.1       Introduction 18.2       Synthesis of Isoindolines 18.2.1    [2+2+2] Cycloaddition Reactions 18.2.2    Transition Metal-promoted Diels-Alder reactions 18.2.3    Transition Metal-promoted Cyclization of Ortho-substituted Benzyl Amines (and Derivatives) 18.2.4    Transition Metal-promoted 5-exo-dig Cyclization by C-C Bond Formation 18.2.5    Miscellaneous 18.2.6    Conclusions and Perspectives References   19          1,2-Benzisothiazole 1,1-Dioxide (Saccharinate)-Based Compounds: Synthesis, Reactivity and    Applications                Luís M.T. Frija, André L. Fernandes, Bruno Guerreiro, and M. Lurdes S. Cristiano   19.1       Introduction 19.2       Synthesis of Saccharinate-based Conjugates 19.3       Applications 19.3.1    Ionic Liquids 19.3.2    Coordination Chemistry 19.3.3    Biological Activity and Medical Uses 19.4       Concluding Remarks References   20          Fused Heterocycles                Arruje Hameed, Muhammad Abdul Qayyum, Abdur Rehman, Touseef Ur Rehman, Anwar Ahmad, and Tahir Farooq   20.1       Introduction 20.1       Recent Developments for Facile Synthesis and Applications of 1,2,4-Triazole Fused Heterocycles 20.1.1    1,2,4-Triazole-fused Heterocycles as Energetic Materials 20.1.2    1,2,4-Triazole-fused Heterocycles as Building Blocks 20.2       Recent Developments for Facile Synthesis of 1,2,3-Triazole-fused Heterocycles 20.2.1    1,2,3-Triazole-fused Heterocycles as Bioactive Scaffolds 20.2.2    1,2,3-Triazole-fused Heterocycles as Functional Materials 20.3       Conclusion References     21          Recent Advances in the Design and Synthesis of Cyclic Peptidomimetics                Arruje Hameed, Amjad Hameed, Ghulam Hussain, Hafiz Abdul Qayyum, Muhammad Fayyaz Farid, and Tahir Farooq   21.1       Introduction 21.2       Click-mediated Approaches for Cyclic Peptidomimetics 21.3       Enzyme-mediated Approaches for Cyclic Peptidomimetics 21.4       Solid-phase Synthesis of Cyclic Peptidomimetics 21.5       Conclusion References