More Synthetic Approaches to Nonaromatic Nitrogen Heterocycles, 2 Volume Set

Ana Maria M.M. Faisca Phillips, PhD, is Researcher at the Coordination Chemistry and Catalysis Group, Centro de Química Estrutural, Instituto Superior Técnico Universidade de Lisboa.

• List of ContributorsPrefaceList of Common Abbreviations  PART 1: CASCADE REACTIONS  1             Unity is Strength: The Case of Cascade Reactions Combined with C–H Activation  1Emanuele  Casali, Ervis Saraci and Giuseppe Zanoni               1.1         Introduction1.2         Rhodium Promoted Reactions1.3         Palladium Promoted Reactions1.4         Ruthenium Promoted Reactions1.5         Cobalt Promoted Reactions1.6         MiscellaneousReferences  2             Chemo-enzymatic Cascade Reactions for the Synthesis of Chiral Intermediatesand Nonaromatic Nitrogen HeterocyclesRodrigo 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         Introduction2.2         C–N Bond Construction Enzymes2.3         C–N Deracemization Enzymes2.4         Cascade Reactions2.4.1      Enzymatic Cascade Reactions2.4.2      Chemoenzymatic Cascade ReactionsReferences  3             Asymmetric Organocatalytic Cascade Reactions for the Synthesis of Nitrogen HeterocyclesA. M. M. M. Faisca Phillips  3.1 Introduction3.2 Three-membered Ring Heterocycles: Aziridines3.3 Four-membered Ring Heterocycles: The β-lactams3.4 Five-membered Rings3.4.1 Pyrrolidines3.4.2 Pyrrolidinones (-Lactams)3.4.3 Isoindolinones and Spirooxindoles3.5 Six-membered Rings3.5.1 Piperidines, Dihydropyridines and Tetrahydropyridines3.5.2 Piperidinones (-lactams)3.5.3 Dihydropyridinones3.5.4 Tetrahydroquinolines, Dihydroquinolines and Related Substances3.5.5 Hexahydropyridazines and Pyrimidinones3.6 Pyrrolo[3,2,1-ij]quinolines3.7 Cyclic Sulfamidates3.8 MiscellaneousConclusionReferences    PART 2: SELECTED REACTIONS FOR THE SYNTHESIS OF NITROGEN HETEROCYCLES  4             Synthesis of Nitrogen-Heterocycles Based on N-Heterocyclic Carbene OrganocatalysisHideto Miyabe                 4.1         Introduction4.2         NHC-catalyzed Cyclization4.3         NHC-catalyzed Annulation4.3.1      [3 + 2] Annulation4.3.2      [4 + 2] Annulation4.3.3      [3 + 3] Annulation4.3.4      [4 + 3] Annulation4.3.5      [2 + 2] Annulation4.4         Oxidative NHC-catalyzed Annulation4.4.1      Oxidative [3 + 2] Annulation4.4.2      Oxidative [4 + 2] Annulation4.4.3      Oxidative [3 + 3] Annulation4.4.4      Oxidative [4 + 3] Annulation4.4.5      Oxidative [2 + 2] Annulation4.5         Asymmetric Dearomatization4.6         Cooperative Catalysis of NHC and Transition-Metal Catalysts4.7         Other NHC-catalyzed Reactions4.8         Conclusion and OutlookReferences  5             Synthesis of N-Heterocycles via [3 + n] Cycloaddition Reactions of Vinyl Metal Carbene IntermediatesMing Bao, Su Zhou, and Xinfang Xu                 5.1         Introduction5.2         [3 + 1]-Cycloaddition5.3         [3 + 2]-Cycloaddition5.4         [3 + 3]-Cycloaddition5.4.1      [3 + 3]-Cycloaddition with Nitrone5.4.2      [3 + 3]-Cycloaddition with Azomethine Imines5.4.3      [3 + 3]-Cycloaddition with Other 1,3-Dipoles5.5         [3 + 4]-Cycloaddition5.5.1      [3 + 4]-Cycloaddition with N-Heterocycles5.5.2      [3 + 4]-Cycloaddition with α,-Unsaturated Imines5.5.        Other Types of [3 + 4]-Cycloadditions5.6         [3 + 5]-Cycloaddition5.7         Intramolecular Cyclization via Carbene/Alkyne Metathesis Process5.8         Summary and OutlookReferences  6             Recent Progress in the Synthesis of Amine-containing Heterocycles by Metathesis ReactionsZeyue Zhang, Damien Hazelard, and Philippe Compain                 6.1         Introduction6.2         Five-membered Cyclic Amines6.3         Six-membered Cyclic Amines6.3.1      Natural Products and Related Compounds6.3.2      Sugar Mimetics6.3.3      RCM of Phenylamines and Related Analogues6.3.4      Miscellaneous6.4         Seven-membered to Macrocyclic Amines6.5         Tandem Reactions6.6         ConclusionReferences  7             Metal-Catalyzed Synthesis of N-Heterocycles Via Borrowing-Hydrogen AnnulationA. Sofia Santos, Daniel Raydan, Nuno Viduedo, M. Manuel B. Marques, and Beatriz Royo  7.1         Introduction7.2         Metal-Catalyzed Borrowing Hydrogen Annulation Reactions7.2.1      Rh-Catalyzed Borrowing Hydrogen Reactions7.2.2      Ru-Catalyzed Borrowing Hydrogen Reactions7.2.3      Ir-Catalyzed Borrowing Hydrogen Reactions7.2.4      Fe-Catalyzed Borrowing Hydrogen Reactions7.2.5      Ni-Catalyzed Borrowing Hydrogen Reactions7.3         ConclusionsReferences  8             Synthesis of N-Heterocycles Via Metal-Catalyzed Intramolecular Buchwald-Hartwig C-N Cross Coupling ReactionsAuxiliadora Prieto  8.1         Introduction8.2.        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-Heterocycles8.2.4.     Synthesis of Seven-membered N-Heterocycles8.3.        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-Heterocycles8.3.3.     Application in the Synthesis of Seven-membered N-Heterocycles8.4.        Intramolecular Pd-Catalyzed Arylation of Sulfonamides.8.5         Applications of the Intramolecular Buchwald-Hartwig Amination in the Synthesis of Natural Products.8.6         ConclusionReferences  9             Synthesis of Nonaromatic Nitrogen Heterocycles Via Singlet OxygenJoão Tomé, Kelly A.D.F. Castro, Leandro M. O. Lourenço, Roberto Santana Da Silva,                 9.1         Introduction9.2         Singlet Oxygen on Organic Synthesis9.2.1      Oxidation of Bipyrroles9.2.2      Synthesis of (R)-methylnaltrexone9.2.3      Synthesis of Glochidine and Glochidicine9.2.4      Synthesis of γ-lactams via One-pot Synthesis9.2.5      Synthesis of the Melohenine B9.2.6      Synthesis of Pyrrolidine Derivatives by [2 + 3] Cycloaddition, via 1O2 Mediated 1,3-dipole9.2.7      Synthesis of Pandamarine9.2.8      Preparation of Bicyclic Lactam9.2.9      Synthesis of Alkaloids9.2.10   Synthesis of Azaspiro Frameworks9.2.11 Preparation of Tetrahydropyranopyrrolones9.2.12 Synthesis of 2-oxindoles9.2.13 Synthesis of Several Natural Products from an Amino Furan Derivative9.2.14 Synthesis of Peptide-fluorescent Probes9.2.15 Synthesis of Tetrahydroquinoline9.3         ConclusionReferences  10           Cobalt-catalysed Carbonylation for the Synthesis of N-Heterocyclic CompoundsAnup Paul and Armando J.L. Pombeiro                 1.            Introduction2.            Cobalt-catalysed Carbonylation for the Synthesis of N-heterocyclic Compounds Using CO Gas as CO source3.            Cobalt-catalysed Carbonylation for the Snthesis of N-heterocycles Using CO Surrogates4.            ConclusionsReferences  11           Enantioselective Synthesis of Nitrogen Heterocycles Using Chiral Hypervalent Iodine ReagentsAna Maria Faisca Phillips and Armando J.L. Pombeiro  11.1       Introduction11.2       The Historical Development of Chiral Hypervalent Iodine Reagents11.3       Synthesis with Chiral Hypervalent Iodine Reagents11.3.1   Difunctionalization of Alkenes11.3.2   Dearomatization Reactions11.3.3   α-Functionalization of Carbonyl Compounds11.4       ConclusionReferences  PART III. SPECIAL TECHNIQUES  12           Continuous Flow ChemistryMarcus Baumann                 12.1       Introduction To Modern Flow Chemistry12.2       Value of Heterocyclic Chemistry for Modern Drug Discovery Programs12.3       Case Studies of Flow Chemistry Applied to Heterocyclic Targets12.3.1    Flow Synthesis of Three-membered Saturated Heterocycles12.3.2    Flow Synthesis of Four-membered Saturated Heterocycles12.3.3    Flow Synthesis of Five-membered Saturated Heterocycles12.3.4    Flow Synthesis of Six-membered Saturated Heterocycles12.3.5    Flow Synthesis of Seven-membered Saturated Heterocycles12.3.6    Flow Synthesis of Macrocyclic Saturated Heterocycles12.4       Assessment of the Merits of Continuous Flow Processing for Heterocycle Synthesis12.5       Summary and ConclusionsReferences  13           The Electrochemical Synthesis of Non-Aromatic N-HeterocyclesOana R. Luca  13.1       Introduction13.2       Laws of Organic Electrosynthesis13.2.1    Types of Electrolyses13.2.2    Diagnostic Analytical Methods: Voltammetry13.3.      Construction of Three- and Four Membered Non-Aromatic Heterocycles13.3.1 Aziridines13.3.2 Epoxides13.3.3 Azetidines13.4       Construction of Five Six and Seven Membered Non-Aromatic Heterocycles13.4.1   Pyrrolidines13.4.2   Indolines and dihydrobenzofurans13.4.3   Pyrrolidinones, 5-membered Cyclic Carbamates and Derivatives13.4.4   Tetrahydrooxazole and Tetrahydrooxazine Derivatives13.4.5   6-membered Amides, Carbamates, and Derivatives13.5       Construction of Nonaromatic Heterocycles with Fused Polycyclic Systems13.5.1   Nonaromatic Heterocycles from Phtalimides and Succinimides13.5.2   Polyciclic Peptides13.5.3   Polyclic Ureas13.5.5   Ring-fused QuinonesConclusionReferences  14          Asymmetric Organocatalysis in Alternative MediaLuis C. Branco, Verônica Diniz, Karolina Zalewska, and Miguel M. Santos                 14.1       Introduction14.2       Water as Reaction Medium14.3       Ionic Liquids as Alternative Media14.4       Miscellaneous Alternative Reaction Media14.5       ConclusionsReferences  PART IV. SYNTHETIC METHODS FOR SPECIAL COMPOUND CLASSES  15           The Strained Aziridinium IonJala Ranjith and Hyun-Joon Ha                 15.1       Introduction15.2       Formation of Aziridinium Ions15.3       Ring Opening of Aziridinium Ion15.4       Synthetic Applications15.5       Bicyclic Aziridinium Ion and its ApplicationAckowledgmentsReferences  16           Recent advances on the synthesis of azepane-based compoundsMaria Assunta Chiacchio, Laura Legnani, Ugo Chiacchio, and Daniela Iannazzo  16.1       Introduction16.2       Azepane Synthesis16.2.1    Synthesis of Substituted Azepanes16.2.2 Synthesis of Ring-fused Azepanes16.2.3 Synthesis of Azepane-based AlkaloidsConclusion                17           1,4-Diazepane Ring-based SystemsEduarda M.P. Silva, Pedro A.M.M. Varandas, and Artur M.S. Silva  17.1       Introduction17.2       Reductive Amination17.3       Mitsunobu Amination17.4       1,3-Dipolar Cycloaddition17.5       Multicomponent Reactions17.6       Other MethodsConclusionsReferences  18           Transition Metal Promoted Synthesis of Isoindoline DerivativesLaura A. Aronica and Gianluigi Albano  18.1       Introduction18.2       Synthesis of Isoindolines18.2.1    [2+2+2] Cycloaddition Reactions18.2.2    Transition Metal-promoted Diels-Alder reactions18.2.3    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 Formation18.2.5    Miscellaneous18.2.6    Conclusions and PerspectivesReferences  19          1,2-Benzisothiazole 1,1-Dioxide (Saccharinate)-Based Compounds: Synthesis, Reactivity and    ApplicationsLuís M.T. Frija, André L. Fernandes, Bruno Guerreiro, and M. Lurdes S. Cristiano  19.1       Introduction19.2       Synthesis of Saccharinate-based Conjugates19.3       Applications19.3.1    Ionic Liquids19.3.2    Coordination Chemistry19.3.3    Biological Activity and Medical Uses19.4       Concluding RemarksReferences  20          Fused HeterocyclesArruje Hameed, Muhammad Abdul Qayyum, Abdur Rehman, Touseef Ur Rehman, Anwar Ahmad, and Tahir Farooq  20.1       Introduction20.1       Recent Developments for Facile Synthesis and Applications of 1,2,4-Triazole Fused Heterocycles20.1.1    1,2,4-Triazole-fused Heterocycles as Energetic Materials20.1.2    1,2,4-Triazole-fused Heterocycles as Building Blocks20.2       Recent Developments for Facile Synthesis of 1,2,3-Triazole-fused Heterocycles20.2.1    1,2,3-Triazole-fused Heterocycles as Bioactive Scaffolds20.2.2    1,2,3-Triazole-fused Heterocycles as Functional Materials20.3       ConclusionReferences    21          Recent Advances in the Design and Synthesis of Cyclic PeptidomimeticsArruje Hameed, Amjad Hameed, Ghulam Hussain, Hafiz Abdul Qayyum, Muhammad Fayyaz Farid, and Tahir Farooq  21.1       Introduction21.2       Click-mediated Approaches for Cyclic Peptidomimetics21.3       Enzyme-mediated Approaches for Cyclic Peptidomimetics21.4       Solid-phase Synthesis of Cyclic Peptidomimetics21.5       ConclusionReferences