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This dissertation, "Amine synthesis using tandem aza-witting/imine reduction reactions" by Qi, Meng, 孟琪, was obtained from The University of Hong Kong (Pokfulam, Hong Kong) and is being sold pursuant to Creative Commons: Attribution 3.0 Hong Kong License. The content of this dissertation has not been altered in any way. We have altered the formatting in order to facilitate the ease of printing and reading of the dissertation. All rights not granted by the above license are retained by the author. Abstract: Nowadays, both secondary and tertiary amines are playing vital roles in modern chemical industry as well as pharmaceutical industry. Various synthetic methods of amines have also been reported due to their promising applications. In this thesis, a simple and widely applicable one-pot aza-Wittig/reduction method is reported for synthesizing both secondary and tertiary amines. Firstly, we focused on tandem aza-Wittig/reduction reactions for synthesizing secondary amines. We noticed that an aza-Wittig reaction involving an iminophosphrane which is the product from a Staudinger reaction, followed by addition of an aldehyde can be used to construct a C=N double bond in the product. By making use of the PPh3O (byproduct of aza-Wittig reactions) as the catalyst along with trichlorosilane as the reducing agent, the imine products in the aza-Wittig reactions can be converted into amines in one pot. In addition to using PPh3, highly-efficient heterogeneous polystyrene-based rasta resin-supported PPh3 was also examined in our study. Secondly, in order to broaden the utility of this one-pot method, instead of using relatively dangerous organic azides as substrates, in situ azide formation reaction was added to the flow chart. By reacting alkyl bromides with sodium azide or tertabutylammonium azide can give various azides in one-pot. Thirdly, the secondary amines formed using our one-pot procedure can undergo reductive amination reaction with aldehyde to give diverse tertiary amines as the final products in one pot. In this reaction, trichlorosilane reduction was performed twice by utilizing the phosphine oxide byproduct from the aza-Wittig reaction as a catalyst. Finally, chemistry regarding tandem one-pot aza-Wittig reaction by using catalytic amount of phosphine oxide was discussed. Instead of using organic azides, various aryl isocyanates were used as substrates for the reaction, with the help of catalytic amount of a five-membered ring phosphine oxide to give high yields of secondary amines. Chemistry studied in the thesis stands as solid proof for the superiority of our method. Tandem one-pot reactions improved the efficiency of our method by avoiding lengthy workup and purification steps. Our chemistry may serve as a good alternative for both secondary and tertiary amine synthesis in the future. DOI: 10.5353/th_b5177335 Subjects: Amines - Synthesis
Discover a comprehensive overview of efficient synthetic routes to an important compound class in organic and pharmaceutical chemistry Methodologies in Amine Synthesis: Challenges and Applications delivers powerful and state-of-the-art methods for the efficient preparation of amines. The text summarizes recent advances in the electrophilic amination reaction, hydroamination, C-H amination and newly developed photocatalytic approaches. The distinguished editor has included resources that discuss organocatalytic and enzymatic routes to the generation of amines under mild and environmentally friendly conditions. The book also highlights the relevance of the amino function in bioactive molecules, drugs, and smart materials, as well as the palladium-catalyzed aromatic amination reaction. It presents efficient and practical synthetic methods, highlights the opportunities and challenges associated with each, and discusses their possible applications in pharmaceutical chemistry and materials science. Edited by the expert who wrote Modern Amination Methods and Amino Group Chemistry, the book includes a breadth and depth of material essential to the practice of academic and industrial chemists working in organic synthesis and catalysis. Readers will also benefit from the inclusion of: A thorough introduction to new openings and perspectives in the electrophilic amination Discussions of asymmetric catalysed hydroaminomethylation and amino organocatalysis A treatment of the synthetic application of transaminase or MAO biocatalysis to the synthesis of amines An exploration of recent developments in C-H amination, as well as photocatalytic approaches to the synthesis of amines An examination of primary amines from renewable bio-based resources Perfect for organic, natural product, catalytic, medicinal, and polymer chemists, Methodologies in Amine Synthesis: Challenges and Applications will also earn a place in the libraries of materials scientists and chemists working with organometallics who desire a one-stop reference edited by a well-known expert in the field.
Designed for practitioners of organic synthesis, this book helps chemists understand and take advantage of rearrangement reactions to enhance the synthesis of useful chemical compounds. Provides ready access to the genesis, mechanisms, and synthetic utility of rearrangement reactions Emphasizes strategic synthetic planning and implementation Covers 20 different rearrangement reactions Includes applications for synthesizing compounds useful as natural products, medicinal compounds, functional materials, and physical organic chemistry
Domino reactions enable you to build complex structures in one-pot reactions without the need to isolate intermediates- a dream comes true. In this book, the well-respected expert, Professor Lutz Tietze, summarizes the possibilities of this reaction type - an approach for an efficiant, economically benificial and ecological benign synthesis. A definite must for every organic chemist.
Kurti and Czako have produced an indispensable tool for specialists and non-specialists in organic chemistry. This innovative reference work includes 250 organic reactions and their strategic use in the synthesis of complex natural and unnatural products. Reactions are thoroughly discussed in a convenient, two-page layout--using full color. Its comprehensive coverage, superb organization, quality of presentation, and wealth of references, make this a necessity for every organic chemist. * The first reference work on named reactions to present colored schemes for easier understanding* 250 frequently used named reactions are presented in a convenient two-page layout with numerous examples* An opening list of abbreviations includes both structures and chemical names * Contains more than 10,000 references grouped by seminal papers, reviews, modifications, and theoretical works * Appendices list reactions in order of discovery, group by contemporary usage, and provide additional study tools* Extensive index quickly locates information using words found in text and drawings
This practical, well-organized reference delves deeply into functional group transformations, to provide all the detailed information that researchers need. Topics are organized into the following sections: oxidation, reduction, asymmetric synthesis, and functional group manipulations Each section includes a description of the functional group transformation, the historical perspective, mechanisms, variations and improvements on the reaction, synthetic utilities and applications for the reaction, experimental details, and references to the primary literature Contributors are well-known and respected for their work on the specific name reactions.
With the increase in volume, velocity and variety of information, researchers can find it difficult to keep up to date with the literature in their field. This invaluable volume contains analysed, evaluated and distilled information on the latest in carbohydrate research. The discovery and synthesis of novel carbohydrates and mimetics with diverse applications continues to be a major challenge for carbohydrate chemists. The understanding of the structure and function of carbohydrates and glycoconjugates remains vital in medicine and molecular biology. This volume collates modern carbohydrate research from theory to application and demonstrates the importance of carbohydrates in new lead generation. It is of benefit to any researcher who wishes to learn about the latest developments in the carbohydrate field.
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