New Synthetic Methods with Allylstannanes and Aziridines PDF Download
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Author: Joseph Bernard Sweeney
Publisher:
ISBN:
Category : Chemistry, Organic
Languages : en
Pages : 0
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Author: Joseph Bernard Sweeney
Publisher:
ISBN:
Category : Chemistry, Organic
Languages : en
Pages : 0
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Book Description
Author: Joseph Bernard Sweeney
Publisher:
ISBN:
Category : Organic compounds
Languages : en
Pages :
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Author: Andrei K. Yudin
Publisher: John Wiley & Sons
ISBN: 9783527312139
Category : Science
Languages : en
Pages : 532
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Book Description
Aziridines and epoxides are among the most widely used intermediates in organic synthesis, acting as precursors to complex molecules due to the strains incorporated in their skeletons. Besides their importance as reactive intermediates, many biologically active compounds also contain these three-membered rings. Filling a gap in the literature, this clearly structured book presents the much needed information in a compact and concise way. The renowned editor has succeeded in gathering together excellent authors to cover synthesis, applications, and the biological aspects in equal depth. Divided roughly equally between aziridines and epoxides, the twelve chapters discuss: * Synthesis of aziridines * Nucleophilic ring-opening of aziridines and epoxides * Organic synthesis with aziridine building blocks * Vinyl aziridines in organic synthesis * Diastereoselective aziridination reagents * Synthetic aspects of aziridinomitocene chemistry * Biosynthesis of biologically important aziridines * Organic catalysis of epoxide and aziridine ring formation * Metal-mediated synthesis of epoxides * Asymmetric epoxide ring opening chemistry * Epoxides in complex molecule synthesis * Biological activity of epoxide-containing molecules A high-quality reference manual for academic and industrial chemists alike.
Author: Iain David Glean Watson
Publisher:
ISBN: 9780494217894
Category :
Languages : en
Pages : 334
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Book Description
The reactivity of the synthesized non-activated aziridines was examined. Non-activated aziridines were found to be reactive to a number of different nucleophiles. In particular, the ring opening reactions of non-activated aziridines with amine nucleophiles was efficiently catalyzed by tris-(pentafluorophenyl)borane leading to derivatives of trans-1,2-diamines in high yields. A mechanistic investigation of the reaction suggests that in situ formed [(C 6F5)3B(OH2)]·H2O catalyses the opening through a Brensted acid manifold. Conversion of allyl aziridines into alpha-aziridino aldehydes creates reactive intermediates that react with nucleophiles without destruction of the aziridine ring. The conversion from allyl aziridines takes advantage of the high enantioselectivities and unique regioselectivities achieved by the palladium catalyzed process. Finally, the application of non-activated aziridines towards the synthesis of a number of radiolabelled beta-adrenergic agonists and antagonists was undertaken, providing a concrete example of the usefulness of aziridines as reactive intermediates in organic synthesis.*Investigations into the synthesis and reactivity of non-activated aziridines were undertaken. 1 New synthetic methodologies for the synthesis of non-activated aziridines were developed by the N-functionalization of NH-aziridines. In particular, the palladium-catalyzed allylic amination of N-unsubstituted aziridines has been carried out. The use of NH aziridines as nucleophiles favors formation of branched products in the case of aliphatic allyl acetates. The regioselectivity of this reaction is opposite to that observed when other amines are used as nucleophiles. These studies provide evidence for the palladium-catalyzed isomerization of the branched (kinetic) product formed with common secondary amines into the thermodynamic (linear) product. On the contrary, the branched allyl products obtained from N-unsubstituted aziridines do not undergo the isomerization process. The methodology addresses the important issue of forming quaternary carbon centers next to nitrogen. The new insights into the mechanism of palladium-catalyzed allylic amination obtained will facilitate the synthesis of complex heterocycles and the design of new ligands to control branched/linear ratio as well as absolute stereochemistry of allyl amines. 1 (a) Watson, I.D.G.; Yu, L.; Yudin, A.K. Advances in nitrogen transfer reactions involving aziridines. Acc. Chem. Res. 2006, 39, 194-206. (b) Watson, I.D.G.; Yudin, A.K. New insights into the mechanism of palladium-catalyzed allylic amination. J. Am. Chem. Soc. 2005, 127, 17516 - 17529. (c) Watson, I.D.G.; Styler, S.A.; Yudin, A.K. Unusual selectivity of unprotected aziridines in palladium-catalyzed allylic amination enables facile preparation of branched aziridines. J. Am. Chem. Soc. 2004, 126, 5086-5087. (d) Watson, I.D.G.; Yudin, A.K. Ring-opening reactions of nonactivated aziridines catalyzed by tris(pentafluorophenyl)borane. J. Org. Chem. 2003, 68, 5160-5167. (e) Watson, I.D.G.; Yudin, A.K. Selective functionalization of small organic molecules using electrophilic nitrogen sources. Curr. Opin. Drug Discovery Dev. 2002, 5, 906-917. *Please refer to dissertation for diagrams.
Author: Navjeet Kaur
Publisher: Elsevier
ISBN: 0443220603
Category : Science
Languages : en
Pages : 354
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Book Description
The smallest possible saturated azaheterocycle, aziridine, is well-known to organic chemists for its tremendous potential in pharmaceutical chemistry and organic synthesis. The general biological importance of aziridines is proven by the fact that they found several uses as subunits in pharmacologically active compounds such as antitumor agents, enzyme inhibitors, and antibiotics. Although aziridines are highly reactive, this framework occurs in many synthetic compounds and the natural products of biological interest also contain aziridine skeleton in their structures. The synthetic community is captivated with prospects of selective synthesis and conversions of aziridines. Several important advances in this area have been witnessed in recent years and discovering efficient novel methods for the synthesis of aziridines has been very active field of research. Its powerful synthetic utility has been described by an overpowering amount of documentation on the approaches for the formation of aziridine. Synthesis of Aziridines and Oxaziridines from Imines describes the new and old methods for the synthesis of aziridines from imines and covers an important and rapidly growing branch of heterocyclic chemistry. Readers will have access to different methods and information allowing them to evaluate which method is most suitable for particular cases. - Focuses on the biological importance of different heterocycles - Describes traditional and innovative methods for the synthesis of aziridines from imines - Includes comparison amongst different methods, reagents, reaction conditions in tabulated forms, advantages, disadvantages, and critical analysis of different methodologies with respect to their comparison with green technique
Author: Gang Greg Chen
Publisher:
ISBN: 9780494393925
Category :
Languages : en
Pages : 514
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This thesis contains three parts of research, all of which are focused on utilizing aziridines as the intermediates to synthesize valuable building blocks or bioactive structures. The aziridine functionality, a three-membered ring structure containing a nitrogen atom, is widely used in synthesis for chemical bond elaborations and functional group transformations. The most important synthetic application of aziridines is their ring opening reactions which take advantage of strain in the three-membered ring. Other special properties such as oxidative stability or weak basicity have seldom been considered as the rationale for synthetic methodology development or utilized in synthetic route design. In the first part of this thesis, the oxidative stability of aziridines was utilized to carry out a sequence of cyclization and aziridine-opening transformations. The process provides straightforward synthetic entries into a range of larger heterocyclic structures (such as five-membered ring pyrrolidine or six-membered ring piperidine) which are often found in the bioactive natural products or pharmaceuticals. This methodology is of significance in term of generating libraries of the nitrogen heterocycles. The broad scope of substrates used in this research demonstrates the potential value of this methodology. The second part of this thesis deals with an application of the above methodology towards the natural product ficellomycin. Ficellomycin is a naturally occurring antibiotic which shows in vivo antibacterial activity. Due to its rare chemical structure, no successful total synthesis has been reported. We noticed that our aziridine cyclization methodology can be applied to the synthesis of ficellomycin. In this thesis, two synthetic approaches were developed to construct the core structure of ficellomycin. The control of the relative stereochemistry provides an opportunity to synthesize the diastereomeric analogs of ficellomycin. In the third part of the thesis, synthesis of allyl amines from 2-ketoaziridines has been studied. Allyl amine structures are often found in natural products and pharmaceuticals. The hydrazinolysis of 2-ketoaziridines were found to afford allyl amines and pyrazoles. The reaction condition was optimized. The electronic and steric effects from the substituents were studied. A variety of 2-ketoaziridines were transformed into diversely substituted linear or cyclic allyl amines in good yields using this methodology.
Author: Eckehard V. Dehmlow
Publisher: Wiley-VCH
ISBN:
Category : Science
Languages : en
Pages : 260
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Author: Robert Arthur Clark
Publisher:
ISBN:
Category : Organic compounds
Languages : en
Pages : 204
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Author: Eric John Stoner
Publisher:
ISBN:
Category :
Languages : en
Pages : 424
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Author: Lorenzo Checchia
Publisher:
ISBN:
Category :
Languages : en
Pages :
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