This first-of-its-kind four-volume book series, Amino Acids: Insights and Roles in Heterocyclic Chemistry, provides readers with up-to-date information on alpha-amino acids, the potential challenges in working with alpha-amino acids, the protecting groups for the carboxyl, amino and side chain groups of the amino acids, and the most popular heterocyclic compounds that are originating from alpha-amino acids. These heterocyclic compounds include hydantoins, thiohydantoins (including 2-thiohydantoins, 4-thiohydantoins, 2,4-dithiohydantoins), 2,5-diketopiperazines, N-carboxyanhydrides, N-thiocarboxyanhydrides, sydnones, sydnonimines, azlactones, pseudoazlactones, and oxazolidin-5-ones. This is the first resource to comprehensively collect all the heterocycles that can be directly prepared from alpha-amino acids. In addition, almost all kinds of synthetic methods for a particular type of heterocycles from alpha-amino acids are include, along with the detailed mechanistic discussions and experimental procedures.
Volume 4: Azlactones and Oxazolidin-5-ones discusses two types of simple heterocycles that can be prepared from alpha-amino acids, i.e., azlactones (also known as oxazolones, 4-unsaturated azlactones included) and oxazolidin-5-ones. These heterocyclic compounds behave differently in both biological and chemical properties, and their biological activities are presented in a well-organized manner in this volume
Author(s): Zerong Wang
Series: Amino Acids: Insights and Roles in Heterocyclic Chemistry
Publisher: CRC Press/Apple Academic Press
Year: 2023
Language: English
Pages: 432
City: Palm Bay
Cover
Half Title
Amino Acids: Insights and Roles in Heterocyclic Chemistry Series
Amino Acids: Insights and Roles in Heterocyclic Chemistry, Volume 4: Azlactones and Oxazolidin-5-ones
Copyright
About the Editors
Contents
Abbreviations
Acknowledgments
Preface
Preface for Amino Acids: Insights and Roles in Heterocyclic Chemistry
1. Azlactones
1.1 Introduction
1.2 Biological Activities
1.3 Preparative Methods
1.3.1 Preparation of Unsaturated Azlactones
1.3.1.1 Erlenmeyer Azlactone Synthesis
1.3.1.1.1 Erlenmeyer Azlactone Synthesis Under Basic Conditions
1.3.1.1.2 Erlenmeyer Azlactone Synthesis Under Neutral Conditions
1.3.1.1.3 Erlenmeyer Azlactone Synthesis Under Acidic Conditions
1.3.1.2 Alternative Methods for the Preparation of Unsaturated Azlactones
1.3.1.3 Configuration of the Exocyclic Double Bond in Unsaturated Azlactones
1.3.2 Preparation of Saturated Azlactones
1.3.3 Mechanisms for the Formation of Azlactones
1.4 Reactions
1.4.1 Chemical Reactivities of Saturated Azlactones
1.4.1.1 Reactions AT C2 of Azlactones
1.4.1.2 Reactions AT C4 of Azlactones
1.4.1.2.1 Alkylation of Azlactones
1.4.1.2.2 Allylic Alkylation of Azlactones
1.4.1.2.3 Benzylation of Azlactones
1.4.1.2.4 Arylation of Azlactones
1.4.1.2.5 Carboxylation of Azlactones, the Steglich Rearrangement
1.4.1.2.6 Acylation of Azlactones
1.4.1.2.7 Alkynylation of Azlactones
1.4.1.2.8 Aldol Condensation of Azlactones
1.4.1.2.9 Mannich Reaction
1.4.1.2.10 Michael Reaction
1.4.1.2.11 Addition to Isolated Alkenes or Ene Reactions
1.4.1.2.12 Addition to Alkynes
1.4.1.2.13 Addition to Diazo Compounds
1.4.1.2.14 Addition to Allenes
1.4.1.2.15 Miscellaneous Reactions at C4 of Azlactones
1.4.1.3 Reactions AT C5 of Azlactones
1.4.1.3.1 Reactions with Amines
1.4.1.3.2 Reactions with Alcohols
1.4.1.3.3 Reactions with Thiols
1.4.1.3.4 Reactions with Oximes
1.4.1.3.5 Miscellaneous Reactions at C5 of Azlactones
1.4.1.4 Cycloadditions
1.4.1.4.1 1,3-Dipolar Cycloaddition
1.4.1.4.2 [4+2] Cycloaddition
1.4.1.4.3 [8+2] Cycloaddition
1.4.2 Chemical Reactivities of Unsaturated Azlactones
1.4.2.1 Nucleophilic Vinylogous Reactivity of Olefinic Azlactones
1.4.2.2 Vinylogous Arylation of Azlactones
1.4.2.3 Reactions of Unsaturated Azlactones with Carbon Nucleophiles
1.4.2.4 Nucleophilic Addition of Benzimidamide to Unsaturated Azlactones
1.4.2.5 The Reaction of Unsaturated Azlactones with Water
1.4.2.6 The Reaction of Unsaturated Azlactones with Amines
1.4.2.7 Azidolysis of Unsaturated Azlactones
1.4.2.8 Reaction of Hydrazine with Unsaturated Azlactones
1.4.2.9 The Reaction of Alcohols or Thiols with Unsaturated Azlactones
1.4.2.10 Oxygenation of Unsaturated Azlactones
1.4.2.11 1,3-Dipolar Cycloaddition with Exocyclic Double Bond of Unsaturated Azlactones
1.4.2.12 [4+2] Cycloaddition with Exocyclic Double Bond of Unsaturated Azlactones
1.4.2.13 Cyclopropanation of Unsaturated Azlactones
1.4.2.14 Photodimerization of Unsaturated Azlactones
1.4.2.15 Miscellaneous Reaction of Unsaturated Azlactones
1.5 Applications
1.6 Pseudoazlactones
1.7 Final Comments
Keywords
References
2. Oxazolidin-5-ones
2.1 Introduction
2.2 Natural Occurrence
2.3 Biological Activities
2.3.1 Antibacterial and Antimicrobial Activities
2.3.2 Anticancer Activity and Cleavage of DNA
2.3.3 Signal Molecules
2.4 Preparative Methods
2.4.1 Preparation of Oxazolidin-5-Ones from α-Amino Acid Derivatives and Formaldehyde
2.4.2 Preparation of Oxazolidin-5-Ones from α-Amino Acid Derivatives and Acetaldehyde
2.4.3 Preparation of Oxazolidin-5-Ones from α-Amino Acid Derivatives and Benzaldehyde
2.4.4 Preparation of Oxazolidin-5-Ones from α-Amino Acid Derivatives and Pivalaldehyde (t-BuCHO)
2.4.5 Preparation of Oxazolidin-5-Ones from α-Amino Acid Derivatives and Other Aldehydes
2.4.6 Preparation of Oxazolidin-5-Ones from α-Amino Acid Derivatives and Acetone
2.4.7 Preparation of Oxazolidin-5-Ones from α-Amino Acid Derivatives and Hexafluoroacetone
2.4.8 Preparation of Oxazolidin-5-Ones from α-Amino Acid Derivatives and Other Ketones
2.4.9 Preparation of Oxazolidin-5-Ones from α-Amino Acid Derivatives and Alternative Compounds
2.5 Reactions of Oxazolidin-5-Ones
2.5.1 Oxazolidin-5-Ones in Alkylation AT C-4
2.5.2 Formation of N-Methyl Amino Acids
2.5.3 Oxazolidin-5-Ones in Nucleophilic Addition
2.5.4 Decarboxylation to Mesoionic Species for 1,3-Dipolar Cycloaddition
2.5.5 Proline Catalyzed Reactions
2.5.6 Temporary Protection of α-Amino and Carboxyl Groups
2.5.7 Preparation of Peptides
2.5.8 Reactions Occurring AT C5 of Oxazolidin-5-Ones
2.5.9 Miscellaneous Reaction of Oxazolidin-5-Ones
2.6 Applications
Keywords
References
Index
