Microwave-assisted Synthesis of Small Ring Thia-Aza Mixed-donor Ligands PDF Download
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Author: Aaron M. Lineberry
Publisher:
ISBN:
Category : Chemistry
Languages : en
Pages : 153
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Book Description
Given the continued interest in the use of enantioselective metal-catalyzed asymmetric reactions in organic synthesis, there have been considerable research efforts in the development of new chiral ligands consisting of mixed-donor heteroatoms. This dissertation involves the microwave-assisted synthesis of amino acid-derived pyrrolidine thioethers, as well as a thiolane-based analogue consisting of meso frameworks as opposed to the conventional C2 symmetry found in most chiral ligands. Chapter I of this work gives a brief literature review in the synthesis and applications of pyrrolidine-based ligand systems. Also discussed is a review of 3-pyrroline derivatives, which are an important class of heterocycles used as precursors in the synthesis of 3,4-disubstituted pyrrolidines, as well as several synthetic approaches towards their preparation. Chapter II of this work describes the microwave-assisted synthesis of a series of chiral amino acid-derived pyrrolidine diols, from the appropriate L-amino acid methyl ester hydrochlorides (Leu, Val, Phe) or benzyl esters (Gly, Ala, Ser) and cis-1,4-dichloro-2-butene. The enantiopurity of the chiral 3-pyrroline intermediates have been established through Mosher ester synthesis and by comparison of optical rotation of the amino acid esters. Also, the attempted conversion of the diols into thioethers is discussed. The multi-step synthesis of thiolane analogues, as well as approaches towards novel heterobicyclo[4.3.0]nonanes is discussed. Finally, a modified approach towards the tripodal ligand system [9]aneN2S and a microwave-assisted cyclization of [9]aneN3 are discussed.
Author: Aaron M. Lineberry
Publisher:
ISBN:
Category : Chemistry
Languages : en
Pages : 153
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Book Description
Given the continued interest in the use of enantioselective metal-catalyzed asymmetric reactions in organic synthesis, there have been considerable research efforts in the development of new chiral ligands consisting of mixed-donor heteroatoms. This dissertation involves the microwave-assisted synthesis of amino acid-derived pyrrolidine thioethers, as well as a thiolane-based analogue consisting of meso frameworks as opposed to the conventional C2 symmetry found in most chiral ligands. Chapter I of this work gives a brief literature review in the synthesis and applications of pyrrolidine-based ligand systems. Also discussed is a review of 3-pyrroline derivatives, which are an important class of heterocycles used as precursors in the synthesis of 3,4-disubstituted pyrrolidines, as well as several synthetic approaches towards their preparation. Chapter II of this work describes the microwave-assisted synthesis of a series of chiral amino acid-derived pyrrolidine diols, from the appropriate L-amino acid methyl ester hydrochlorides (Leu, Val, Phe) or benzyl esters (Gly, Ala, Ser) and cis-1,4-dichloro-2-butene. The enantiopurity of the chiral 3-pyrroline intermediates have been established through Mosher ester synthesis and by comparison of optical rotation of the amino acid esters. Also, the attempted conversion of the diols into thioethers is discussed. The multi-step synthesis of thiolane analogues, as well as approaches towards novel heterobicyclo[4.3.0]nonanes is discussed. Finally, a modified approach towards the tripodal ligand system [9]aneN2S and a microwave-assisted cyclization of [9]aneN3 are discussed.
Author: Tia Louise Walker
Publisher:
ISBN:
Category : Chemistry
Languages : en
Pages : 287
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Book Description
Following the structural characterization and analysis of Blue Copper Proteins (BCP's), macrocyclic ligands have attracted much interest as simple models for naturally occurring metal-macrocycle centers. Presented in this dissertation are the syntheses and characterization of small, simple organic analogs of BCP's. Chapter I of this work gives a brief literature review of Blue Copper Proteins, including their unique spectral characteristics. The synthesis and characterization of several linear and cyclic molecular analogs will be discussed including polythiaethers,3 polyazacycloalkanes,4 thia-aza5 and trithiaethers. The macrocyclic effect will be explained and why cyclic molecular analogs are of current interest. Presented in the second chapter are the syntheses of two 14-membered rings with a 2,3,2,3 altering carbon chain arrangement for 1,8-dithia-4,11-diazacyclotetradecane and 1,11-dithia-4,8-diazacyclotetradecane. The 1,8-dithia-4,11-diazacyclotetradecane is complexed to both Cu2+ and Cu+ and fully characterized using UV-Vis, EPR and CV. The 1,11-dithia-4,8-diazacyclotetradecane was synthesized for structural X-ray comparison of the Cu2+ metal ion. The 1,8-dithia-4,11-diazacyclotetradecane having two nitrogen atoms also makes it attractive for functionalization. Presented in the third chapter of this dissertation is the expansion of these ligands for use as cryptands. The syntheses of two cryptands are fully described and include crystallographic data. One of the cryptand ligands, 1,8-dithia-4,11,18,21-tetraazatricyclo[10.6.6]pentacosane-25-one was successfully complexed to Cu2+ and those results are also discussed. To further conclude this research is a pendant arm derivative and its synthesis. Each nitrogen atom of 1,8-dithia-4,11-diazacyclotetradecane is functionalized with a four carbon chain connecting to 1,4-diaza-7-thiacyclononane.
Author: Wilhelm S. Malasi
Publisher:
ISBN:
Category : Cancer
Languages : en
Pages : 210
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Book Description
"Six ligands of mixed thia-aza donor atoms 40, 90, 100, 107, 110 and 112 have been synthesized and characterized. The metal complexes of Copper 114, Rhodium 116, and Nickel 115 with 1,8-dithia-4,11-diazacyclotetradecane 40 have been made and crystal structures grown in appropriate solvents to give good crystals suitable for X-ray crystallographic analysis. Other molecules whose crystals have been made and analyzed by X-ray crystallography are the secondary amine 82, tosylated double ligand tertiary amine 91, the seven member ring ester 100 and the perchlorate salt of the double nine member ligand tertiary amine 110. All these crystals have their analysis data in the appendix D. The seventh ligand 113 has been adapted, and complexed with rhodium and its crystal structure 117 has been analyzed. The curative activity of the rhodium complex 116 was tested against ovarian cancer cells Nutu-19 at 1.54 mM concentrations. The results showed that the cells became detached with extreme morphological changes and extreme internal vesicle formation causing the cells to die. Ovarian normal cells, tested at the same concentration, showed that the cells remain attached, with no morphological changes and only slightly vesicle formation. Table 4 in chapter 2 shows 87% of the cancer cells died while only 30% of the normal ovarian cells died. If the toxicity of this complex can be further controlled and minimized, it may be very useful in the treatment of cancer in the future. The ligand 40 was functionalized through carboxylic acid derivatives to give rise to the new ligand 90. Also ligand 107 was functionalized in the same way to give the new ligand 110, while the liands 82 and 107 were successfully joined by a butane chain to form a new ligand 112. In an attempt to synthesize the carbon bridged functionalized fourteen membered ring, ligand 99, the functionalized seven membered ring molecule 100 was isolated instead."--Abstract.
Author: Cai Huang
Publisher: BoD – Books on Demand
ISBN: 9535107372
Category : Medical
Languages : en
Pages : 482
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Book Description
15 chapters on protein phosphorylation and human health written by expert scientists. Covers most important research hot points, such as Akt, AMPK and mTOR. Bridges the basic protein phosphorylation pathways with human health and diseases. Detailed and comprehensive text with excellent figure illustration.
Author: Peter G. M. Wuts
Publisher: John Wiley & Sons
ISBN: 1118589327
Category : Science
Languages : en
Pages : 1108
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Book Description
The Fourth Edition of Greene's Protective Groups in Organic Synthesis continues to be an indispensable reference for controlling the reactivity of the most common functional groups during a synthetic sequence. This new edition incorporates the significant developments in the field since publication of the third edition in 1998, including... New protective groups such as the fluorous family and the uniquely removable 2-methoxybenzenesulfonyl group for the protection of amines New techniques for the formation and cleavage of existing protective groups, with examples to illustrate each new technique Expanded coverage of the unexpected side reactions that occur with protective groups New chart covering the selective deprotection of silyl ethers 3,100 new references from the professional literature The content is organized around the functional group to be protected, and ranges from the simplest to the most complex and highly specialized protective groups.
Author: Tsutomu Ishikawa
Publisher: John Wiley & Sons
ISBN: 9780470740866
Category : Science
Languages : en
Pages : 336
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Book Description
Guanidines, amidines and phosphazenes have been attracting attention in organic synthesis due to their potential functionality resulting from their extremely strong basicity. They are also promising catalysts because of their potential for easy molecular modification, possible recyclability, and reduced or zero toxicity. Importantly, these molecules can be derived as natural products – valuable as scientists move towards “sustainable chemistry”, where reagents and catalysts are derived from biomaterial sources. Superbases for Organic Synthesis is an essential guide to these important molecules for preparative organic synthesis. Topics covered include the following aspects: an introduction to organosuperbases physicochemical properties of organic superbases amidines and guanidines in organic synthesis phosphazene: preparation, reaction and catalytic role polymer-supported organosuperbases application of organosuperbases to total synthesis related organocatalysts: proton sponges and urea derivatives amidines and guanidines in natural products and medicines Superbases for Organic Synthesis is a comprehensive, authoritative and up-to-date guide to these important reagents for organic chemists, drug discovery researchers and those interested in the chemistry of natural products.
Author: Takahiko Akiyama
Publisher: John Wiley & Sons
ISBN: 1119736412
Category : Science
Languages : en
Pages : 798
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Book Description
Catalytic Asymmetric Synthesis Seminal text presenting detailed accounts of the most important catalytic asymmetric reactions known today This book covers the preparation of enantiomerically pure or enriched chemical compounds by use of chiral catalyst molecules. While reviewing the most important catalytic methods for asymmetric organic synthesis, this book highlights the most important and recent developments in catalytic asymmetric synthesis. Edited by two well-qualified experts, sample topics covered in the work include: Metal catalysis, organocatalysis, photoredox catalysis, enzyme catalysis C–H bond functionalization reactions Carbon–carbon bond formation reactions, carbon–halogen bond formation reactions, hydrogenations, polymerizations, flow reactions Axially chiral compounds Retaining the best of its predecessors but now thoroughly up to date with the important and recent developments in catalytic asymmetric synthesis, the 4th edition of Catalytic Asymmetric Synthesis serves as an excellent desktop reference and text for researchers and students, from upper-level undergraduates all the way to experienced professionals in industry or academia.
Author: Rajender Boddula
Publisher: Elsevier
ISBN: 0128198516
Category : Technology & Engineering
Languages : en
Pages : 242
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Book Description
Green Sustainable Process for Chemical and Environmental Engineering and Science: Switchable Solvents explores the preparation, properties, chemical processes and applications of this class of green solvents. The book provides an in-depth overview on the area of switchable solvents in various industrial applications, focusing on the purification and extraction of chemical compounds utilizing green chemistry protocols that include liquid-liquid, solid-liquid, liquid-gas and lipids separation technologies. In addition, it includes recent advances in greener extraction and separation processes. This book will be an invaluable guide to students, professors, scientists and R&D industrial specialists working in the field of sustainable chemistry, organic, analytical, chemical engineering, environmental and pharmaceutical sciences. - Provides a broad overview of switchable solvents in sustainable chemical processes - Compares the use of switchable solvents as greener solvents over conventional solvents - Outlines eco-friendly organic synthesis and chemical processes using switchable solvents - Lists various industrial separations/extraction processes using switchable solvents
Author: Catherine E. Housecroft
Publisher: MDPI
ISBN: 3036514635
Category : Science
Languages : en
Pages : 264
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Book Description
This Special Issue is one of the first for the new MDPI flagship journal Chemistry (ISSN 2624-8549) which has a broad remit for publishing original research in all areas of chemistry. The theme of this issue is Supramolecular Chemistry in the 3rd Millennium and I am sure that this topic will attract many exciting contributions. We chose this topic because it encompasses the unity of contemporary pluridisciplinary science, in which organic, inorganic, physical and theoretical chemists work together with molecular biologists and physicists to develop a systems-level understanding of molecular interactions. The description of supramolecular chemistry as 'chemistry beyond the molecule' (Jean-Marie Lehn, Nobel Lecture and Gautam R. Desiraju, Nature, 2001, 412, 397) addresses the wide variety of weak, non-covalent interactions that are the basis for the assembly of supramolecular architectures, molecular receptors and molecular recognition, programed molecular systems, dynamic combinatorial libraries, coordination networks and functional supramolecular materials. We welcome submissions from all disciplines involved in this exciting and evolving area of science.
Author: Piet W.N.M. van Leeuwen
Publisher: Springer Science & Business Media
ISBN: 0306469472
Category : Science
Languages : en
Pages : 291
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Book Description
In the last decade there have been numerous advances in the area of rhodium-catalyzed hydroformylation, such as highly selective catalysts of industrial importance, new insights into mechanisms of the reaction, very selective asymmetric catalysts, in situ characterization and application to organic synthesis. The views on hydroformylation which still prevail in the current textbooks have become obsolete in several respects. Therefore, it was felt timely to collect these advances in a book. The book contains a series of chapters discussing several rhodium systems arranged according to ligand type, including asymmetric ligands, a chapter on applications in organic chemistry, a chapter on modern processes and separations, and a chapter on catalyst preparation and laboratory techniques. This book concentrates on highlights, rather than a concise review mentioning all articles in just one line. The book aims at an audience of advanced students, experts in the field, and scientists from related fields. The didactic approach also makes it useful as a guide for an advanced course.
