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Relevant bibliographies by topics / Aza-Heterocycles- Synthesis

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Academic literature on the topic 'Aza-Heterocycles- Synthesis'

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Published: 6 September 2023

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Journal articles on the topic "Aza-Heterocycles- Synthesis"

1

Chamberlain, Anna E. R., Kieran J. Paterson, Roly J. Armstrong, Heather C. Twin, and Timothy J. Donohoe. "A hydrogen borrowing annulation strategy for the stereocontrolled synthesis of saturated aza-heterocycles." Chemical Communications 56, no. 24 (2020): 3563–66. http://dx.doi.org/10.1039/d0cc00903b.

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Rulev, A. Yu, and A. R. Romanov. "Unsaturated polyfluoroalkyl ketones in the synthesis of nitrogen-bearing heterocycles." RSC Advances 6, no. 3 (2016): 1984–98. http://dx.doi.org/10.1039/c5ra23759a.

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Zonker, Benjamin, Ediz Duman, Heike Hausmann, Jonathan Becker, and Radim Hrdina. "[1,2]-Rearrangement of iminium salts provides access to heterocycles with adamantane scaffold." Organic & Biomolecular Chemistry 18, no. 26 (2020): 4941–45. http://dx.doi.org/10.1039/d0ob01156h.

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4

Singh, Deepak, and Hyun-Joon Ha. "Metal-free aza-Claisen type ring expansion of vinyl aziridines: an expeditious synthesis of seven membered N-heterocycles." Organic & Biomolecular Chemistry 17, no. 12 (2019): 3093–97. http://dx.doi.org/10.1039/c8ob03029d.

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5

Frontier, Alison J., Shukree Abdul-Rashed, and Connor Holt. "Alkynyl Prins and Alkynyl Aza-Prins Annulations: Scope and Synthetic Applications." Synthesis 52, no. 14 (April 9, 2020): 1991–2007. http://dx.doi.org/10.1055/s-0039-1690869.

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This review focuses on alkynyl Prins and alkynyl aza-Prins cyclization processes, which involve intramolecular coupling of an alkyne with either an oxocarbenium or iminium electrophile. The oxocarbenium or iminium species can be generated through condensation- or elimination-type processes, to achieve an overall bimolecular annulation that enables the synthesis of both oxygen- and nitrogen-containing saturated heterocycles with different ring sizes and substitution patterns. Also discussed are cascade processes in which alkynyl Prins heterocyclic adducts react to trigger subsequent pericyclic reactions, including [4+2] cycloadditions and Nazarov electrocyclizations, to rapidly construct complex small molecules. Finally, examples of the use of alkynyl Prins and alkynyl aza-Prins reactions in the synthesis of natural products are described. The review covers the literature through the end of 2019.1 Introduction1.1 Alkyne-Carbonyl Coupling Pathways1.2 Coupling/Cyclization Cascades Using the Alkynyl Prins Reaction2 Alkynyl Prins Annulation (Oxocarbenium Electrophiles)2.1 Early Work2.2 Halide as Terminal Nucleophile2.3 Oxygen as Terminal Nucleophile2.4 Arene as Terminal Nucleophile (Intermolecular)2.5 Arene Terminal Nucleophile (Intramolecular)2.6 Cyclizations Terminated by Elimination3 Synthetic Utility of Alkynyl Prins Annulation3.1 Alkynyl Prins-Mediated Synthesis of Dienes for a [4+2] Cyclo- addition-Oxidation Sequence3.2 Alkynyl Prins Cyclization Adducts as Nazarov Cyclization Precursors3.3 Alkynyl Prins Cyclization in Natural Product Synthesis4 Alkynyl Aza-Prins Annulation4.1 Iminium Electrophiles4.2 Activated Iminium Electrophiles5 Alkynyl Aza-Prins Cyclizations in Natural Product Synthesis6 Summary and Outlook

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Gusar, N. I. "Synthesis of heterocycles by the aza-Wittig reaction." Russian Chemical Reviews 60, no. 2 (February 28, 1991): 146–61. http://dx.doi.org/10.1070/rc1991v060n02abeh001036.

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7

Yang, Xu-Heng, Jian Huang, Fang Wang, Zhuoliang Liu, Yujiao Li, Cheng-an Tao, and Jianfang Wang. "Copper-catalyzed alkynylation/annulation cascades of N-allyl ynamides: regioselective access to medium-sized N-heterocycles." Organic Chemistry Frontiers 8, no. 1 (2021): 18–24. http://dx.doi.org/10.1039/d0qo00837k.

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A synthetic strategy based on sequential application of aza-Claisen rearrangement, C–H functionalization, C–N coupling and cyclization as key steps has been developed for the synthesis of 6-, 7-, 8-, and 9-membered rings N-heterocycles.

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Guin, Soumitra, Debashis Majee, and Sampak Samanta. "Unmasking the reverse reactivity of cyclic N-sulfonyl ketimines: multifaceted applications in organic synthesis." Chemical Communications 57, no. 72 (2021): 9010–28. http://dx.doi.org/10.1039/d1cc03439a.

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This feature article covers the recent status on the reactivities of α-alkyl cyclic N-sulfonyl ketimines as resourceful nucleophiles, targeting fused carbo- and heterocycles, aza-arenes etc. In addition, the mechanistic studies have been presented.

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Seath, Ciaran P., Kirsty L. Wilson, Angus Campbell, Jenna M. Mowat, and Allan J. B. Watson. "Synthesis of 2-BMIDA 6,5-bicyclic heterocycles by Cu(i)/Pd(0)/Cu(ii) cascade catalysis of 2-iodoaniline/phenols." Chemical Communications 52, no. 56 (2016): 8703–6. http://dx.doi.org/10.1039/c6cc04554e.

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A one-pot cascade reaction for the synthesis of 2-BMIDA 6,5-bicyclic heterocycles has been developed using Cu(i)/Pd(0)/Cu(ii) catalysis. The method provides efficient access to borylated indoles, benzofurans, and aza-derivatives, which can be difficult to access through alternative methods.

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Nguyen, Thi Thu Tram, Le Anh Nguyen, Quoc Anh Ngo, Marina Koleski, and Thanh Binh Nguyen. "The catalytic role of elemental sulfur in the DMSO-promoted oxidative coupling of methylhetarenes with amines: synthesis of thioamides and bis-aza-heterocycles." Organic Chemistry Frontiers 8, no. 7 (2021): 1593–98. http://dx.doi.org/10.1039/d0qo01654c.

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Dissertations / Theses on the topic "Aza-Heterocycles- Synthesis"

1

McGonagle, Alison Elizabeth. "Synthesis of nitrogen-containing heterocycles using novel aza-Wittig methodology." Thesis, University of Leeds, 2007. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.439563.

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Race, Nicholas J. "Development of aza-Heck cyclisations for the synthesis of chiral nitrogen heterocycles." Thesis, University of Bristol, 2015. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.681733.

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The synthesis of chiral N-heterocycles through palladium- and copper-catalysed aza-Heck cyclisations of oxime esters has been developed. Initial studies focussed on the development of a palladium-catalysed aza-Heck-π-allyl cascade with carbon, nitrogen and hydride nucleophiles. These reactions were limited to oxime esters bearing gem-α-disubstitution. Investigation into aza-Heck cyclisations involving 1,2-disubstituted alkenes was subsequently undertaken. Here, control of β-hydride elimination regioselectivity was crucial to obtaining chiral products. A series of oxygen-based, sulfur-based and aryl substituents were evaluated for their ability to promote regioselective β-hydride elimination. Both oxygen and sulfur substituents gave low selectivity, whereas aryl groups promoted β-hydride elimination in the direction of chiral products. Catalyst-controlled cyc1isation of alkyl-substituted alkenes provided chiral products and a selectivity model for this process was proposed. Highly diastereoselective manipulations of the dihydropyrrole products obtained from this chemistry allowed access to more complex N-heterocycles. A complementary copper-catalysed aza-Heck cyclisation was next developed. Mechanistic studies of both palladium- and copper-catalysed reactions revealed a mechanistic dichotomy. Reactions involving electron-deficient palladium catalysts proceed through the formation of imino-Pd(II) intermediates, whereas copper catalysts form an iminyl radical, or radical-like species. Reactions involving electron-rich palladium catalysts also resulted in the formation of an iminyl radical, and in the presence of a hydrogen-atom donor formed the product of a 'reductive' aza-Heck reaction. Finally, an enantioselective palladium-catalysed aza-Heck reaction has also been developed. Spirocyclic P,N-based SIPHOX ligands were privileged for this transformation and the synthesis of a series of SIPHOX derivatives allowed the aza-Heck reaction to proceed in high yield and enantioselectivity. A selectivity model was proposed for these reactions

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Faulkner, Adele. "Development of aza-Heck cyclisations and cascades for the synthesis of nitrogen heterocycles." Thesis, University of Bristol, 2015. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.687438.

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Palladium- and copper-catalysed aza-Heck cyclisations of oxime esters with pendant olefins, have been developed for the synthesis of chiral nitrogen heterocycles. Initial studies explored palladium-catalysed cyclisations onto 1,1-disubstituted alkenes to afford α,α-disubstituted dihydropyrroles. A wide range of functional groups are tolerated in this process, showcasing the versatility of this approach. A complementary copper-catalysed aza-Heck has also been developed. Mechanistic studies of these two processes revealed two distinct pathways. Cyclisations employing an electron deficient palladium catalyst proceed via oxidative addition of Pd(O) into the N-O bond of the oxime ester to generate a key imino-Pd(II) intermediate. Migratory insertion of the olefin into the Pd-N bond and subsequent β-hydride elimination delivers α,α-disubstituted dihydropyrroles. Under copper-catalysed conditions, cyclisations proceed via a radical type pathway, involving oxidative initiation at the N-O bonds of oxime esters to generate an iminyl radical or radical-like species. After cyclisation, an alkyl-radical is generated which undergoes oxidative elimination to afford the Nheterocyclic products. An enantioselective palladium-catalysed aza-Heck cyclisation is also described herein. Employment of spirocyclic P,N-based SIPHOX ligands is crucial for efficient cyclisation, which delivered enantioemiched α,α-disubstituted dihydropyrroles in high yield and enantioselectivity. In an alternative strategy for achieving alkene 1,2-carboaminations, cascade aza-Heck cyclisations have been developed. Aza-Heck cyclisation of oxime esters enables access to a versatile alkyl-Pd(II) species, which can be trapped with a variety ofnucleophiles. Olefin 1,2-amino-acylation -carboxylation, -arylation, -vinylation and -alkynylation reactions have been established. An ambitious palladium-catalysed aza-Heck cascade cyclisation has been proposed for the total synthesis of (+)-cylindricine C and studies have examined three key aspects: 1) azaHeck spirocyclisation of oxime esters, 2) asymmetric aza-Heck cyclisations and 3) a carbonylative cascade of oxime esters. Proof-of-concept has been achieved on model substrates and fmiher research is ongoing to realise this challenging total synthesis.

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Hazelden, Ian. "Development of new classes of aza-Heck cyclisation for the synthesis of nitrogen heterocycles." Thesis, University of Bristol, 2019. http://hdl.handle.net/1983/58bca1bd-9538-4c94-9295-6da0b49eb3b2.

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Two novel classes of aza-Heck reactions have been developed. These processes generate 2-alkenyl-N-heterocycles through the palladium-catalysed cyclisation of substrates containing an activated N-O bond and a pendant olefin. The first of these, based on the cyclisation of N-acyloxysulfonamides, is only the second reported class of aza-Heck reaction and is effective for the synthesis of complex bicyclic N-heterocycles commonly found in the core structures of natural products. Subsequently, an aza-Heck reaction of N-acyloxycarbamates was developed that provides considerable improvements in terms of efficiency compared to the sulfonamide-based reaction. Through the cyclisation of N-acyloxycarbamates, pyrrolidines and piperidines, as well as related 5- and 6-membered N-heterocycles, can be prepared in good to excellent yields. Furthermore, the diastereoselectivities achieved in these processes are generally much greater than those observed with aza-Heck cyclisations of N-acyloxysulfonamides. A number of mechanistic experiments have validated the aza-Heck pathway proposed for these transformations. A highly asymmetric variant of the aza-Heck reaction was also developed, based on the cyclisation of N-sulfonyloxycarbamates. Through the use of SPINOL-based phosphoramidite ligands, pyrrolidines and piperidines can be prepared in good yields and with high enantioselectivities from substrates containing a diverse range of alkenes. Additionally, palladium(0)-catalysed cascade reactions using the previously developed N-O bond donors have been demonstrated. These processes initiate with N-O oxidative addition and aminopalladation of a pendant alkene but terminate with trapping of the resulting organopalladium(II) intermediate, as opposed to b-hydride elimination. In collaboration with co-workers, a variety of alkene 1,2-aminofunctionalisation cascades have been achieved using this strategy. The application of these cascade reactions to the total synthesis of natural products has also been attempted.

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Lepitre, Thomas. "Modulation des Processus Domino au départ des Accepteurs de Michael en série Chromone : Diversité par aza-Cyclisation, Arylation et Aryloxylation Métallocatalysées : Diversité par aza-Cyclisation, Arylation et Aryloxylation Métallocatalysées." Thesis, Normandie, 2017. http://www.theses.fr/2017NORMLH31/document.

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Le concept de la DOS (Diversity-Oriented Synthesis) est une nouvelle approche qui vise à générer des collections de petites molécules avec des hauts degrés de diversité et de complexité structurale. Diverses stratégies ont été mises en place pour y parvenir de manière la plus efficace possible à partir de simples substrats de départ.Dans ce contexte, ce travail de thèse a permis de montrer comment un processus domino avait tout le potentiel à être exploité en tant que formidable outil dans le cadre d’une approche DOS, générateur à la fois de complexité mais également de diversité structurale. Un précurseur connu et largement étudié pour son caractère exceptionnellement versatile a été valorisé dans ce contexte : la 3-formylchromone. Dans ce manuscrit, nous montrerons comment il est possible de moduler le cours d’un processus domino pour atteindre de hauts degrés de diversité structurale, à partir des chromones accepteurs de Michael-1,6 et d’amines primaires. Nous verrons en particulier comment le contrôle d'une ou de plusieurs étapes clefs des séquences réactionnelles impliquées peut être réalisé selon :(I) la modulation pertinente d’une ou plusieurs unité(s) de structure au sein des substrats de départ, (II) la modulation des paramètres réactionnels (solvants, température, additifs), et(III) l’induction d’un changement de réactivité au sein d’un intermédiaire réactionnel par addition d’un agent externe
In the early 2000s a general consensus has emerged in which the molecular diversity within a given library of small molecules, rather than its size, has been recognized as a crucial requirement. Diversity-oriented synthesis (DOS) has emerged from this new paradigm. This novel approach aims to generate collections of small molecules with high degrees of structural diversity, in the most efficient way, starting from simple building-blocks. Since the generation of collections of structurally diverse small molecules in a DOS-driven approach constitutes a real challenge, diverse strategies have been set up for this purpose.In this line, this work has shed light on the great potential of a domino process as a valuable tool in a DOS-driven strategy, capable of generating both molecular diversity and architectural complexity. This study has been focused on the 3-formylchromone building block, a particular framework which has already proven being an exceptionally versatile precursor of molecular diversity. In this manuscript, we will highlight how it is possible to modulate the course of a domino process to achieve high degrees of molecular diversity, starting from the chromone based 1,6-Michael acceptors platform and primary amines as reaction partners. In particular we will show how it is feasible to control the course of particular steps involved in the domino process through: (I) the pertinent modulation of the Michael acceptors and the primary amines structures, (II) the modulation of the reaction parameters (solvent, temperature, additives), and (III) the tuning of the reactivity within a key reaction intermediate induced by the introduction of an external agent

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Jha, Abadh Kishor. "New strategies towards the functionalization of C-H and C-Cl bond of Aryls(Heteroaryls) and synthesis of Aza-Heterocycles." Thesis, 2018. http://eprint.iitd.ac.in:80//handle/2074/7941.

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Books on the topic "Aza-Heterocycles- Synthesis"

1

D’hooghe, Matthias, and Hyun-Joon Ha. Synthesis of 4- to 7-membered Heterocycles by Ring Expansion: Aza-, oxa- and thiaheterocyclic small-ring systems. Springer, 2015.

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2

D’hooghe, Matthias, and Hyun-Joon Ha. Synthesis of 4- to 7-membered Heterocycles by Ring Expansion: Aza-, oxa- and thiaheterocyclic small-ring systems. Springer, 2019.

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3

Ha, Hyun-Joon, and Matthias D'hooghe. Synthesis of 4- to 7-Membered Heterocycles by Ring Expansion: Aza-, Oxa- and Thiaheterocyclic Small-Ring Systems. Springer London, Limited, 2015.

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Book chapters on the topic "Aza-Heterocycles- Synthesis"

1

Fort, Yves, and Corinne Comoy. "Lithiated Aza-Heterocycles in Modern Synthesis." In Lithium Compounds in Organic Synthesis, 423–62. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2014. http://dx.doi.org/10.1002/9783527667512.ch15.

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2

Zwanenburg, Binne, and Peter ten Holte. "The Synthetic Potential of Three-Membered Ring Aza-Heterocycles." In Stereoselective Heterocyclic Synthesis III, 93–124. Berlin, Heidelberg: Springer Berlin Heidelberg, 2001. http://dx.doi.org/10.1007/3-540-44726-1_3.

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3

"Diastereoselective and Enantioselective Construction of Aza-Heterocycles." In Organic Synthesis, 138–39. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2006. http://dx.doi.org/10.1002/0470056312.ch70.

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4

"Recent Trends in Metal Nanoparticles (MNPs) Catalyzed Synthesis of Aza- and Oxa-Heterocycles." In Advanced Nanocatalysis for Organic Synthesis and Electroanalysis, edited by Tejas M. Dhameliya, Rutvi J. Patel, Normi D. Gajjar, Rajvi H. Amin, Kunjan B. Bodiwala, and Dipen K. Sureja, 114–57. BENTHAM SCIENCE PUBLISHERS, 2022. http://dx.doi.org/10.2174/9789815040166122010009.

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Singh, Girija S., and Tumelo H. Tabane. "Synthetic Approaches to Small- and Medium-Size Aza-Heterocycles in Aqueous Media." In Green Synthetic Approaches for Biologically Relevant Heterocycles, 163–84. Elsevier, 2015. http://dx.doi.org/10.1016/b978-0-12-800070-0.00007-4.

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Singh, Girija S. "An update on synthetic methods for small and medium aza-heterocycles in aqueous media." In Green Synthetic Approaches for Biologically Relevant Heterocycles, 505–35. Elsevier, 2021. http://dx.doi.org/10.1016/b978-0-12-820792-5.00011-1.

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Conference papers on the topic "Aza-Heterocycles- Synthesis"

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Rosa, Fernanda A., Michael J. V. da Silva, Davana S. Gonçalves, Daniela H. Arita, Camila S. S. Tozatti, and Gisele de F. G. Bandoch. "Synthetic Application of New Enaminodiketone: Regioespecific Synthesis of Aza-Heterocycles." In 15th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-bmos2013_2013101145054.

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