MCR 2009 (eBook)

Proceedings of the 4th International Conference on Multi-Component Reactions and Related Chemistry, Ekaterinburg, Russia

Maxim A. Mironov (Herausgeber)

eBook Download: PDF

2010 | 2011
X, 230 Seiten
Springer New York (Verlag)
978-1-4419-7270-5 (ISBN)

Infos

Multi-component reactions warrant ever-increasing attention, as they are ideally suited for combinatorial synthesis (either on solid support or in solution) of libraries of products relevant to catalysis, such as agrochemicals or pharmaceuticals. Therefore, the study and implementation of MCRs possesses a wide range of appeal and applicability. A broad and expanding audience of scientists and students continues to apply the concepts of multi-component chemistry to an array of disciplines-this collection of research offers an angle for each and brings together the vast scope of possibilities within the greater community.

Maxim A. Mironov is affiliated with Ural State Technical University, Ekaterinburg, Russian Federation

Inhalt

Contents 6
Introduction to the Proceedings of the Fourth International Conference on Multi-Component Reactions and Related Chemistry 8
Session 1: Catalysis and Multi-Component Reactions 12
Recent Progress in Asymmetric Two-Center Catalysis 13
Efficiency in Chemistry: From Hydrogen Autotransfer to Multi-component Catalysts 15
Multi-component Reactions by Microwave-Assisted, Continuous Flow Organic Synthesis 16
A Potpourri of Recent Microwave-Assisted 2(1H)-Pyrazinone Chemistry 18
Efficient Construction of (Hetero)Aryl Substituted (Aza)Indoles by Pd-Catalyzed Multi-component Reactions 20
Chlorotrimethylsilane is an Efficient Promoter for the Biginelli Reaction 22
Three-Component Synthesis of Dihydropyrimidobenzimidazol Derivatives in the Presence of MgO as a Highly Effective Heterogeneous Base Catalyst 
24 
[Hmim]TFA-Catalyzed Multi-component Reaction: Direct, Mild, and Efficient Procedure for the Synthesis of 1,2-Dihydroquinazolines 
26 
Synthesis of Benzofurans Catalyzed by 1,4-Diazabicyclo[2,2,2]Octane in Solventless System 28
Silica Sulfuric Acid: Highly Efficient Catalyst for the Synthesis of Imidazo[1,2-a]pyridines Using Trimethylsilylcyanide or Cyanohydrins 
29 
Efficient Construction of (Aza)Indolyl Ynones by Pd/Cu-Catalyzed Multi-component Reactions 31
Multi-component Synthesis of Pyridazine and Pyridazinoquinazoline Derivatives in the Presence of 12-Tungstophosphoric Acid 33
Research of Nanosized Metal Oxide Action on Regio- and Stereoselectivity of the Multi-component Hantzsch Reaction 35
Nanocrystalline Copper (II) Oxide-Catalyzed One-pot Synthesis of Polyfunctionalized Pyrans via a Three-Component Cyclocondensation 
 
38 
Reference 14
Session 2: Multi-Component Reactions in Heterocyclic Chemistry 39
Multi-component Synthesis of Heterocycles by Palladium-catalyzed Generation of Alkynones, Alkenones and Allenes 40
Multi-component Reactions as Useful Platforms to Explore the Chemical Space 42
Multi-component Heterocyclizations: Control of Chemo- and Regioselectivity 44
Multi-component Reactions of H2S with Aldehydes and Amines as an Efficient Route to Heterocycles and Thioaza-Crown Compounds 46
Cascade Recyclizations of 1H-Pyrrole-2, 3-diones: A Method of Unusual Heterocyclic Systems Construction 49
Alkyne-Induced Tandem Transformations of (Hetero)Annulated Five-, Six-, or Seven-Membered N-Heterocycles and a New MCR on This Motif 
51 
N–C and C–C Recyclizations of Pyrimidinium Salts 53
Synthetic Approach to Highly Functionalized Mesocyclic Heterocycles by Coupling an Ugi or Passerini Reaction (PADAM Strategy) with a Pd-Mediated Cyclocarbonylation 
55 
Solvent-Free Three-Component Condensation of Aldehydes and Malononitrile with Naphthols Affording 2-Amino-4H-chromenes 57
General Procedure for 2-Amino-4H-Chromenes 57
New Pyrido[3,2-c]pyridones and Pyrido[3,2-c]pyrazoles Accessible by a One-Step Multi-component Synthesis 59
Synthesis of 1-Hydroxyaryl-4-Acyl-5-Aryl-3-Hydroxy-3-Pyrrolin-2-Ones 61
Synthesis of Highly Stable, Unusual Charge-Separated Pyridinium-, Isoquinolinium-, Quinolinium-, and N-Methylimidazolium-Tetronic Acid Zwitterions 
63 
Synthesis of 4(5)-Imidazolecarboxylic Acid Derivatives 64
Polyfunctional U-MCR Reagents: Convenient Pathway to Novel Heterocyclic Systems 67
One-Pot Synthesis of Pyridines by Cyclocondensation of Acetyl- and Benzoylpyruvates, Trimethyl Orthoformate, and Enamines 69
Unprecedented Multi-component Approach to 1,4-Diazepine- and 1,4-Benzodiazepine Ring Formation 71
Synthesis and Interaction with Butylamine of Methyl 6-Acyl-7-Phenyl-4,7-Dihydrotetrazolo[1,5-a]Pyrimidine-5-Carboxylates 72
One-Pot Synthesis of 5-Oxo-1,3,4,5-Tetrahydro-Pyrrolo[4,3,2-de]Isoquinoline-3-Carboxamides 74
Synthesis of 4-Acyl-5-Aryl-1-(2,2-dimethoxyethyl)-3-Hydroxy-3-Pyrrolin-2-Ones 76
Synthesis and Structure of Isopropyl 5-Methyl-7-aryl-4,7-Dihydrotetrazolo[1,5-a]Pyrymidine-6-Carboxylates 78
References 41
Session 3: Multi-Component Reactions in Drug Discovery 80
Multi-component Reactions and Drug Discovery 83
Building Molecular Shape Diversity via Post-Ugi Annulations 84
A Fast and Efficient Approach to Small Molecular Weight Protein-Protein Interaction Antagonists Using MCR Chemistry 86
Molecular Diversification and Solid-Phase Synthesis of N-Acylpeptides for Antibiotic Screening 88
Convertible Products of Ugi Reaction Involving Azole Carboxylic Acids and tert-Butyl Isocyanide 90
Applications of Quinoxaline Synthesis via Isocyanide-Based MCR 92
Continued Evidence for the Utility of TMSCl as Promoter for Groebke-Blackburn Reactions: Synthesis of Imidazo[2,1-b][1,3]benzothiazoles 
94 
Systematic Diversity-Oriented Synthesis Based on Ugi Reaction Products 96
Priaxon AG, a New Dimension in Drug Discovery 99
Isocyanide-Based Multi-component Reaction of Diamines: An Efficient Strategy for Assembling of Unique Heterocyclic Scaffolds 100
A Convenient Synthesis of Novel Heterocyclic Structures Containing 11-Oxo-6,11,12,13-tetrahydrodibenzo[b,g][1,5]oxazonine Fragment 
101 
Synthesis of Substituted 3-Methyl-1-oxo-2,3,4,5-tetrahydro-1H-benzo[C]azepino-3-carboxamides 103
New Approach of Some Bifunctional Initials in U-4MCR 105
One-Step Assembly of Novel Carbamoyl-Substituted Heterocycle-Fused 1-Oxo-2,3-dihydro-1H-benzo[c]azepines 106
A Facile One-Pot Greener Synthesis and Antibacterial Activity of 2-Amino-4H-pyran Derivatives 108
Session 4: Novel Reagents for Multi-Component Reactions 109
Pluripotent Substrates in Diversity-Oriented Synthesis 112
New Polyfunctional Reagents for Isocyanide-Based Multi-component Reactions 114
Products of Ugi Reaction Among Acid Hydrazides, Aldehydes, and Isocyanides with Added Diversity 116
Highly Functionalized Tricyclic N-Heterocycles by Coupling an Ugi MCR with a Tandem Pd(0)-Promoted SN2'-Heck Reaction 
118 
Cascade Transformations of N-(1-Aryl-2-polychloroethyl)sulfonamides 120
New Strategy for the Synthesis of Fluorinated Compounds: Multi-component Reactions Including Fluoro-containing Building Blocks 122
A Multi-component Reaction Leading to a Phenalenone Derivative 124
Heteropoly Acids in One-Pot, Three-Component Synthesis of 4-Aminoquinazolines 125
Passerini Multi-component Reaction of Indane-1,2,3-trione, Isocyanides and 2-Furancarboxylic Acid 127
A Novel Route to the Synthesis of Fluoroalkylated Hexahydroimidazo[1,2-a]Pyridines 128
Exploiting the Secondary Amines and the Glycolaldehyde Dimer in the Ugi Reaction: Formation of a Novel Passerini–Ugi Chimera Scaffold 
130 
Three-Component Synthesis of 4´H-spiro [Adamantane-2,3´-isoqunolines] 131
Nonracemizable Isocyanoacetates for Multi-component Reactions 133
References 111
Short Communication: Synthesis 135
Three-Component Synthesis of 2-Aza-spiro[4.5]decane Derivatives 136
Session 5: Design of Multi-Component Reactions 138
From Ugi–Smiles Couplings to Nef Reaction of Isocyanides 140
The Importance of Being a Secondary Amine: From the N-Split Ugi Reaction of the Reshuffling of the Ugi and Passerini Products 
142 
Rebuilding a Forgotten MCR: Studies on the Interaction of Isocyanides with Alkylboranes and Aldehydes 144
Diversity-Oriented Synthesis of Various Benzo-Fused Oxaza Heterocycles by Coupling the Ugi Reaction with Nucleophilic Substitutions 
145 
New Multi-Component Reactions Based on Electrophilic Activation of Azines 147
Multi-Component Synthesis of New Heterocyclic Compounds from Propynals 149
Synthesis of Partially Hydrogenated Heterocycles: 3,4-Dihydroisoqunolines, Spiropyrrolines, Polyhydroindols 151
Development of Bi- and Multi-component Reactions for the Synthesis of Some Fused Hexahydropyrimines 153
Isocyanide-Based Multi-component Reactions with CF3-Carbonyl Compounds 155
The Investigation of Three-Component Reaction Based on Isocyanides with Olefins and (Thio)phenols 157
Improving the Isocyanide-Based Nef Synthesis: Reaction Between Acyl Chlorides and a-Isocyanoacetamides 159
Cascade Reactions of N-(1-Aryl-2-Polychloroethyl)-Sulfonamides with Mercaptoethanol 161
A New Type of Cascade Reactions, Proceeding in the Presence of Diazocarbonyl Compounds 163
Multistep Process of Nucleophilic Vinylic Substitution of Captodative Halogeno(Carbonyl)Alkenes 165
Postreaction Modifications of U-4CR-Diels-Alder Products 168
Session 6: Multi-Component Reactions in Supramolecular Chemistry and Material Science 170
Derivatization of Readily Available meso-Tetraarylporphyrins 173
Synthesis of 7H-Thiazolo[3,2-a]pyridines by Three-Component Reaction of Thioamides of Malonic Acid with Acrylonitriles and Dimethyl Acetylenedicarboxylate 
175 
Multivariance of New Three-Component System Dicarbonyl Compound: Fullerene C60-tris(dialkylamido)phosphite 177
One-Pot Synthesis of Nitrogen Heterocycles Under Mannich Reaction Conditions 179
Multi-component Synthesis of Pyrrol-Containing Podands Under Heterogeneous Catalysis Conditions 181
Analysis on Hydrogen and Methane Combustion Reactions and Particle Transport in Premixed Flame Reactor 183
Plasma Reactions of NO and SO2 Removal in Dielectric Barrier Discharge: Photocatalysts Hybrid System 184
Chemical Modification of Chitin and Chitosan by Formaldehyde and H2S 186
Structure Diversification and Combinatorial Synthesis of Cyclodecapeptides Based on Natural Laterocidin 188
Modification of Small Chitosan Particles via Multi-Component Reactions 190
Solid-State Synthesis of Chitosan-Polyester Systems for Biomedical Applications 193
Amberlyst A-15: An Efficient Reusable Catalyst for the Synthesis of 2,4,5-tri-Arylimidazole and 1,2,4,5-tetra-Arylimidazole Derivatives 
 
195 
References 172
Conference Program 196
List of Participants 200
Index 213

Produkt-Details

• Erscheint lt. Verlag: 26.10.2010
• Reihe/Serie: Advances in Experimental Medicine and Biology
• Reihe/Serie: Advances in Experimental Medicine and Biology
• Zusatzinfo: X, 230 p.
• Verlagsort: New York
• Sprache: englisch
• Themenwelt: Studium ► 1. Studienabschnitt (Vorklinik) ► Biochemie / Molekularbiologie
• Themenwelt: Naturwissenschaften ► Chemie ► Organische Chemie
• Themenwelt: Technik
• ISBN-10: 1-4419-7270-6 / 1441972706
• ISBN-13: 978-1-4419-7270-5 / 9781441972705