The Chemistry of Ynamides in the Synthesis of Chiral Biaryls and Heterocycles
Author : Whitney Leanne Johnson
Publisher :
Page : 208 pages
File Size : 42,85 MB
Release : 2008
Category :
ISBN :
Author : Whitney Leanne Johnson
Publisher :
Page : 208 pages
File Size : 42,85 MB
Release : 2008
Category :
ISBN :
Author : Gwilherm Evano
Publisher : CRC Press
Page : 733 pages
File Size : 42,58 MB
Release : 2024-06-14
Category : Medical
ISBN : 1003831524
Ynamides contain a triple bond directly connected to a nitrogen atom that bears an electron-withdrawing group. They represent an especially useful and emerging class of reagents, notably because of their strongly polarized triple bond, which enables the development of unique chemical transformations. While they were discovered by Viehe in 1972, their chemistry has remained little investigated and the renaissance of ynamide chemistry started at the dawn of the 20th century with the development of efficient methods for their synthesis. Since then, ynamide chemistry has developed at a remarkably high rate, notably in the past 20 years. Although there are several reviews on ynamide chemistry, most of them are out of date or only focus on special aspects of ynamide chemistry and there is no book about ynamide chemistry yet. Thus, a comprehensive book on ynamide chemistry would be timely and is highly needed. This book covers all aspects of ynamide chemistry, including their discovery, their syntheses, their application in heterocyclic chemistry, natural product synthesis, and organometallic chemistry, and their use as coupling reagents. It provides a systematic and comprehensive overview on ynamide chemistry for the researchers in this field, general readers interested in synthesis, and those who want to enter this field and need a comprehensive and up-to-date overview. Undoubtedly, this book will play a key role in connecting the past with the future to further foster the development of ynamide chemistry.
Author : Tim Wezeman
Publisher : Logos Verlag Berlin GmbH
Page : 253 pages
File Size : 13,5 MB
Release : 2016-12-31
Category : Science
ISBN : 383254397X
Sulfonyl ynamides are highly versatile and synthetically useful reagents. This thesis details the modular synthesis and use of sulfonyl ynamides in order to access N-heterocyclic scaffolds, such as quinolines and pyrazoles. The synthesis of a wide array of sulfonyl ynamides can be realized via copper-catalyzed amidative cross-couplings or by elimination of dichloroenamide precursors. Additionally the use of Sonogashira chemistry to further diversify terminal ynamides and the synthesis of solid-supported ynamides was investigated. Electrophilically-activated amides can be reacted with sulfonyl ynamides in order to access highly functionalized 4-aminoquinolines. The straightforward amide activation procedure with triflic anhydride and 2-chloropyridine was found to tolerate a wide range of substrates, which allowed for the development of a library of 4-aminoquinolines with ease. Moreover, 4-aminopyrazoles can be prepared by reacting terminal sulfonyl ynamides with sydnones under copper catalysis. However, as the copper catalysts were also found to promote the degradation of the ynamides, a copper-free strain-promoted alternative was developed. An in situ prepared 3-azacyclohexyne was found to tolerate a wide array of C-4 substituted sydnones, producing a mixture of both the 3,4- and 4,3-fused pyrazoles in good yields. Additional investigations into heterocyclic methodology led to the development of highly sophisticated, non-symmetrical and axially-chiral dibenzo-1,3-diazepines, -oxazepines and -thiazepines from simple, commercially available anilines. The anilines were coupled to their corresponding reaction partners via a chloromethyl intermediate and the 7-membered ring was subsequently formed using direct arylation.
Author : Jose M Lassaletta
Publisher : World Scientific
Page : 676 pages
File Size : 31,52 MB
Release : 2019-05-23
Category : Science
ISBN : 1786346478
Chapter contribution from Ben Feringa, Nobel Laureate in Chemistry 2016.Atropisomerism and Axial Chirality provides a global survey of the chemistry of axially chiral compounds including biaryls, heterobiaryls, non-biaryl atropisomers, allenes and spyrocyclic derivatives. From the perspective of a synthetic organic chemist, this book provides a unique compilation of the available methodologies for their synthesis, with emphasis on the most efficient and modern strategies, a review of the huge amount of practical applications in the field of asymmetric catalysis, either as transition metal ligands or as organocatalysts, and an overview of their occurrence as bioactive compounds and natural products.The first of its kind, this book serves as a general introduction and a practical reference to advanced chemistry students and researchers, while also offering creative ideas for further developments in the field.
Author : Bin Tan
Publisher : John Wiley & Sons
Page : 338 pages
File Size : 42,77 MB
Release : 2021-11-22
Category : Science
ISBN : 3527347127
Axially Chiral Compounds Explore this comprehensive and current volume summarizing the characteristics, synthesis, and applications of axial chirality Appearing widely in natural products, biologically active molecules, asymmetric chemistry, and material science, axially chiral motifs constitute the core backbones of the majority of chiral ligands and organocatalysts in asymmetric catalysis. In a new work of particular relevance to synthetic chemists, Axially Chiral Compounds: Asymmetric Synthesis and Applications delivers a clearly structured and authoritative volume covering the classification, characteristics, synthesis, and applications of axial chirality. A must read for every synthetic chemist practicing today, the book follows the development history, research status, and applications of axial chirality. An introductory chapter familiarizes the reader with foundational material before the distinguished authors describe the different classes and the synthesis of axial chiral compounds used in asymmetric synthesis. The book concludes with a focus on the applications of chiral ligands, chiral catalysts, and materials. Readers will also benefit from the inclusion of: A thorough introduction to asymmetric synthesis, including biaryls atropisomers, heterobiaryls atropisomers, and non-biaryls atropisomers Explorations of chiral allene, spiro skeletons, and natural products Practical discussions of asymmetric transformation, chiral ligands, and chiral catalysts An examination of miscellaneous applications of axially chiral compounds Perfect for organic chemists, chemists working with or on organometallics, catalytic chemists, and materials scientists, Axially Chiral Compounds: Asymmetric Synthesis and Applications will also earn a place in the libraries of natural products chemists who seek a one-stop reference for compounds exhibiting axial chirality.
Author : Eric F.V. Scriven
Publisher : Elsevier
Page : 296 pages
File Size : 33,51 MB
Release : 2023-02-07
Category : Science
ISBN : 0443193150
Advances in Heterocyclic Chemistry, Volume 139, the latest release in this definitive series on the field of heterocyclic chemistry, combines descriptive synthetic chemistry and mechanistic insights to yield an understanding on how chemistry drives the preparation and useful properties of heterocyclic compounds. Topics in this new release include Application of the Fischer indole synthesis in medicinal chemistry, Oxindole Synthesis via C-H Activation Methods, Ring-Closing Metathesis in the Synthesis of Fused Indole Structures, Synthesis of fuller heterocycles, The Literature of Heterocyclic Chemistry, Part XX, 2020, and Heterocyclic Zwitterions Based on Coupled Polymethines. - Presents what is considered to be the definitive serial in the field of heterocyclic chemistry - Serves as the go-to reference for organic chemists, polymer chemists and many biological scientists - Provides the latest comprehensive reviews written by established authorities in the field - Combines descriptive synthetic chemistry and mechanistic insights to enhance understanding on how chemistry drives the preparation and useful properties of heterocyclic compounds
Author : Christian Wolf
Publisher : Royal Society of Chemistry
Page : 534 pages
File Size : 41,3 MB
Release : 2008
Category : Education
ISBN : 0854042466
A comprehensive overview of fundamental concepts of asymmetric synthesis along with in-depth discussion. Recent developments that address important synthetic challenges are presented and highlighted with hundreds of examples.
Author : Thomas Wirth
Publisher : Springer Science & Business Media
Page : 275 pages
File Size : 11,66 MB
Release : 2003-02-12
Category : Medical
ISBN : 3540441077
T. Wirth: Introduction and General Aspects.- M. Ochiai: Reactivities, Properties and Structures.- A. Varvoglis: Preparation of Hypervalent Iodine Compounds.- V.V. Zhdankin: C-C-Bond Forming Reactions.- G.F. Koser: C- Heteroatom-Bond Forming Reactions.- G.F. Koser: Heteroatom- Heteroatom-Bond Forming Reactions.- T. Wirth: Oxidations and Rearrangements.- H. Tohma, Y. Kita: Synthetic Applications (Total Synthesis and Natural Product Synthesis).
Author : Charles K. Zercher
Publisher : John Wiley & Sons
Page : 1606 pages
File Size : 47,73 MB
Release : 2015-10-19
Category : Science
ISBN : 1118117824
Continuing the tradition of providing significant and interesting procedures, Organic Syntheses, Collective Volume XII is a compilation of revised editions of Annual Volumes 85 through 89. The contents of this volume are organized by primarily by reaction type, with the precise classification made according to the bias of the editor, who attempted to ascertain the primary purpose or utility of the procedure.
Author : Tsutomu Ishikawa
Publisher : John Wiley & Sons
Page : 336 pages
File Size : 31,48 MB
Release : 2009-01-26
Category : Science
ISBN : 9780470740866
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.