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Baumann, Andreas N., Michael Eisold, Arif Music, Geoffrey Haas, Yu Min Kiw, and Dorian Didier. "Methods for the Synthesis of Substituted Azetines." Organic Letters 19, no. 20 (October 4, 2017): 5681–84. http://dx.doi.org/10.1021/acs.orglett.7b02847.
Hodgson, David M., Christopher I. Pearson, and Madiha Kazmi. "Generation and Electrophile Trapping of N-Boc-2-lithio-2-azetine: Synthesis of 2-Substituted 2-Azetines." Organic Letters 16, no. 3 (January 10, 2014): 856–59. http://dx.doi.org/10.1021/ol403626k.
Hodgson, David M., Christopher I. Pearson, and Madiha Kazmi. "ChemInform Abstract: Generation and Electrophile Trapping of N-Boc-2-lithio-2-azetine: Synthesis of 2-Substituted 2-Azetines." ChemInform 45, no. 29 (July 3, 2014): no. http://dx.doi.org/10.1002/chin.201429118.
Didier, Dorian, and Felix Reiners. "Uncommon Four‐Membered Building Blocks – Cyclobutenes, Azetines and Thietes." Chemical Record 21, no. 5 (March 18, 2021): 1144–60. http://dx.doi.org/10.1002/tcr.202100011.
Baumann, Andreas N., Michael Eisold, Arif Music, Geoffrey Haas, Yu Min Kiw, and Dorian Didier. "Correction to Methods for the Synthesis of Substituted Azetines." Organic Letters 19, no. 24 (November 22, 2017): 6763. http://dx.doi.org/10.1021/acs.orglett.7b03520.
Dejaegher, Yves, Sven Mangelinckx, and Norbert De Kimpe. "Rearrangement of 2-Aryl-3,3-dichloroazetidines: Intermediacy of 2-Azetines." Journal of Organic Chemistry 67, no. 7 (April 2002): 2075–81. http://dx.doi.org/10.1021/jo010914j.
Marichev, Kostiantyn O., Kan Wang, Kuiyong Dong, Nicole Greco, Lynée A. Massey, Yongming Deng, Hadi Arman, and Michael P. Doyle. "Synthesis of Chiral Tetrasubstituted Azetidines from Donor–Acceptor Azetines via Asymmetric Copper(I)‐Catalyzed Imido‐Ylide [3+1]‐Cycloaddition with Metallo‐Enolcarbenes." Angewandte Chemie International Edition 58, no. 45 (September 24, 2019): 16188–92. http://dx.doi.org/10.1002/anie.201909929.
Marichev, Kostiantyn O., Kan Wang, Kuiyong Dong, Nicole Greco, Lynée A. Massey, Yongming Deng, Hadi Arman, and Michael P. Doyle. "Synthesis of Chiral Tetrasubstituted Azetidines from Donor–Acceptor Azetines via Asymmetric Copper(I)‐Catalyzed Imido‐Ylide [3+1]‐Cycloaddition with Metallo‐Enolcarbenes." Angewandte Chemie 131, no. 45 (September 24, 2019): 16334–38. http://dx.doi.org/10.1002/ange.201909929.
Dejaegher, Yves, Sven Mangelinckx, and Norbert De Kimpe. "ChemInform Abstract: Rearrangement of 2-Aryl-3,3-dichloroazetidines: Intermediacy of 2-Azetines." ChemInform 33, no. 36 (May 20, 2010): no. http://dx.doi.org/10.1002/chin.200236110.
MacNevin, Christopher J., Rhonda L. Moore, and Dennis C. Liotta. "Stereoselective Synthesis of Quaternary Center Bearing Azetines and Their β-Amino Acid Derivatives." Journal of Organic Chemistry 73, no. 4 (February 2008): 1264–69. http://dx.doi.org/10.1021/jo7018202.
Luheshi, Abdul-Basset Nuri. "Cycloadditions to 1-azetines and 1-azetin-4-ones." Thesis, University of Salford, 1988. https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.327973.
Hemming, Karl. "Studies in the chemistry of 1-azetines and 1-azetin-4-ones." Thesis, University of Salford, 1993. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.334307.
O'Gorman, P. A. "Some aspects of the chemistry of small ring organic molecules : 1-azetines, 1-azetidinones, 3-oxo-β-sultams and cyclopropenones." Thesis, University of Huddersfield, 2009. http://eprints.hud.ac.uk/id/eprint/6310/.
The -lactams and the related -sultams are attractive targets for synthesis because of their central importance in antibiotics such as the penicillins. These heterocycles are of further interest because of their potential as inhibitors of the serine protease class of enzymes113, believed to be responsible for diseases such as rheumatoid arthritis and cystic fibrosis. This thesis will describe the synthesis of the 4-vinyl beta lactams (A)25, thiation of these compounds using Lawesson’s reagent to yield thio lactams (B) and subsequent conversion into the corresponding 1-azetine (C) using Meerwein’s reagent. Compound (C) provided a template for a series of cycloaddition reactions in order to produce a series of bicyclic heterocycles, represented by general structure (D). One reaction that was explored in this series was that between 1-azetines (C) and diphenylcyclopropenone (DPP) (E) which should have yielded the bicyclic adducts F). 93 In the event the products isolated were not the anticipated cycloadducts (F) but rather the ring expanded compounds (G)114 obtained via sigmatropic rearrangement, the nucleus of which is an isomer of the azabicyclononane system, present in many important72 alkaloids such as anatoxin-a (H) and pinnamine (I). The project subsequently evolved to look at the possibility of synthesising other alkaloid nuclei such as the pyrrolizidines, indolizidines and pyrroloazepines through the reaction of the appropriate imines with cyclopropenones. These bicyclic systems are present in many natural products72 such as pyrrolam A (J) and indolizidine 223AB (K) and are of great interest for synthesis because of the wide range of biological activities they possess, such as the ability to block the nicotinic receptor channels. This thesis will therefore describe an effective synthesis of the heterocycles shown in Scheme A (where n = 1, 2 or 3). Further research into the reactions of 4-vinyl -lactams (A) has also been conducted with a view to synthesising analogues of the pyrrolobenzodiazepine, antitumour, antibiotic natural products, of which DC-81 (L) is an example.115 Thus, reaction of (A) with o-azidobenzoylchloride gave the N-substituted -lactam (M). Ring closure via an azide-alkene cycloaddition and loss of nitrogen gave either the aziridine compound (N) or the methyl imine (O). Overall the work described in this thesis pioneers initial research into the reactions of electron rich imines with cyclopropenones, positively demonstrating their use in the synthesis of analogues of alkaloid natural products.
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Pitard, Arnaud. "1-azetines, 1,2-thiazetin-1,1-dioxides and isothiazol-1,1-dioxides as building blocks in heterocyclic synthesis : the attempted synthesis of bicyclic β-sultams." Thesis, University of Huddersfield, 2009. http://eprints.hud.ac.uk/id/eprint/7061/.
This thesis is concerned with the synthesis of β-sultams and the development of new routes for the synthesis of bicyclic versions of these molecules as potential anti-bacterials. The synthesis of 1-azetines, 1,2-thiazetin-1,1-dioxides and isothiazol-1,1-dioxides as precursors of bicyclic heterocycles is described. 1-Azetines were synthesised from azetidin-2-ones prepared via the [2+2] cycloaddition of alkenes with N-chlorosulfonyl isocyanate (CSI). They reacted with diphenylcyclopropenone or nitrile oxides to afford bicyclic systems whose reactivity was explored and afforded a range of heterocycles such as 1,2,4-oxadiazoles, pyridines or pyrimidines via novel reaction pathways. The synthesis of 1,2-thiazetin-1,1-dioxide through two routes will be discussed: the alkylation of 3-oxo-β-sultams to afford 3-ethoxy-1,2-thiazetin-1,1-dioxides, and the ring contraction of an isothiazol-1,1-dioxide to afford a 3-diethylamino-1,2-thiazetin 1,1-dioxide. The reactivity of these 1,2-thiazetin-1,1-dioxides towards diphenylcyclopropenone, 1,3-dipoles and dienes was studied and is fully described. In the course of chemistry mentioned above, a series of isothiazol-1,1-dioxides was synthesised. Their reaction with 1,3-dipoles to yield the corresponding bicyclic heterocycles is described.
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Losa, Romain. "Organocatalyse redox par les phosphines : découverte de nouvelles transformations et vers le développement d'une version électrocatalytique." Electronic Thesis or Diss., université Paris-Saclay, 2024. http://www.theses.fr/2024UPASF014.
Les recherches effectuées dans le cadre de cette thèse se sont portées sur l'organocatalyse par les phosphines trivalentes, des composés jouant un rôle crucial dans de nombreuses transformations chimiques et largement employées dans des synthèses organiques efficaces et variées. L'un des deux axes de recherche de cette thèse s'est concentré sur le développement de nouvelles méthodologies organocatalysées par les phosphines trivalentes. Notre intérêt s'est porté sur des procédés P(III)/P(III) ou P(III)/P(V) permettant la synthèse d'hétérocycles oxygénés ou azotés. Après avoir élaboré une version stœchiométrique en phosphine, nous avons optimisé la méthodologie en la rendant catalytique. Une étude plus approfondie permettant la synthèse de dérivés 2-azétines promue puis catalysée par les phosphines a été développée durant cette thèse. Les produits ainsi obtenus ont pu être valorisés en synthèse organique et testés biologiquement. Enfin, le second axe de recherche mené au cours de cette thèse s'est directement focalisé sur l'électroréduction des oxydes de phosphine cycliques. Dans le contexte environnemental actuel et à la vue des préoccupations écologiques, il est impératif de rendre catalytique en phosphore les réactions promues par les phosphines en introduisant un réducteur dans le milieu réactionnel. Afin d'aller vers le développement de réactions électro-catalytiques, nous avons donc utilisé l'électrochimie pour la réduction des oxydes de phosphine, inscrivant ainsi nos travaux dans une démarche de chimie plus vertueuse This thesis work focused on organocatalysis using trivalent phosphines, compounds which play a crucial role in many chemical transformations and widely used for several organic syntheses. One of the two research axes of this thesis focused on the innovative development of organocatalytic methodologies using trivalent phosphines. We focused on P(III)/P(III) or P(III)/P(V) processes for the synthesis of oxygen or nitrogen-containing heterocycles. After developing a version stoichiometric in phosphine, the methodology was optimized by making it catalytic. A more detailed study enabling the synthesis of 2-azetine derivatives, promoted and then catalysed by phosphines, was developed during this thesis. The products thus obtained were valued in organic synthesis and tested biologically. Finally, the second line of research in this thesis focused directly on the electroreduction of phosphine oxides. In today's environmental context, it is imperative to render the reactions promoted by phosphine catalytic in phosphine, by introducing a reducing agent into the reaction medium. In order to progress towards the development of electrocatalytic reactions, we used electrochemistry for the reduction of phosphine oxides, thus inscribing our work in a more virtuous chemistry approach
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Pearson, Christopher I. "Lithiated azetidine and azetine chemistry." Thesis, University of Oxford, 2014. http://ora.ox.ac.uk/objects/uuid:cf3c942f-80de-4092-a38d-11006ccbb9ce.
This work describes developments in new azetidine and azetine chemistry; specifically, methods developed for the introduction of functionality α- to nitrogen in both ring systems, with additionally in situ formation of the latter system, from azetidine substrates. Chapter 1 discusses the growing importance of azetidines, and the current methods available for making substituted azetidines by ring formation. Further discussion comprises of current sp3 C–H activation approaches α- to nitrogen in heterocyclic compounds as potential methods for sp3 C–H activation on azetidines to give substituted azetidines. Previous work by the Hodgson group in this area is detailed. Chapter 2 describes the advance made towards 2,3-disubstituted azetidines using the thiopivaloyl protecting/activating group, where the latter plays a key role. Optimisation, scope, selectivity and mechanistic insight into the α-deprotonation–electrophile trapping of a 3-hydroxy azetidine system is discussed, which successfully gives access to a range of 3-hydroxy-2-substituted azetidines. Preliminary investigations with 3-alkyl-2-substituted azetidines are also described. Chapter 3 describes the development of a straightforward protocol to make 2-substituted-2- azetines, a rarely studied and difficult to access 4-membered azacycle subclass, from readily accessible azetidine starting materials using α-deprotonation–in situ elimination followed by further α-lithiation–electrophile trapping. Extension of this methodology by transmetallation from the intermediate organolithium to the organocuprate, resulting in greater electrophile scope, is also described.
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Yoshizawa, Akina. "Azetidines for asymmetric synthesis." Thesis, University of Birmingham, 2018. http://etheses.bham.ac.uk//id/eprint/8719/.
The creation of asymmetric ligands with lower environmental impact is important, as such chiral N,N' ligands attract some attention. A new method for the synthesis of 1,2,4-trisubstituted amino azetidines with \(cis\) relative configuration across its two stereogenic centres was reported in 2013. Due to this \(cis\) conformation, the azetidine compounds are expected to be good chiral ligands for asymmetric catalysis. The nitro aldol (Henry) reaction is an established method for producing new carbon-carbon bonds and is a key reaction in the synthesis of many important compounds. Enantioselective Henry reactions generate carbon-carbon bonds and our azetidines are probed as ligands for that reaction. In this work, new azetidines and their palladium and platinum complexes were prepared and characterised by techniques including X-ray diffraction, confirming retention of the \(cis\) conformation. Furthermore, enantiopure \(cis\)-azetidines were used as chiral ligands for a range of transition metals including the use of Cu-azetidine complexes as catalysts for the Henry reaction, in up to >99.5% ee. New enantiopure amino azetidines and their transition metal complexes are demonstrated as asymmetric catalysts for the asymmetric Henry reaction.
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Thaxton, Amber. "Synthesis of Novel Azetidines." ScholarWorks@UNO, 2013. http://scholarworks.uno.edu/td/1764.
Azetidine is a four-membered nitrogen-containing heterocyclic ring that has recently received a great deal of attention as a molecular scaffold for the design and preparation of biologically active compounds. Structure-activity studies employing functionalized azetidines have led to the development of variety of drug molecules and clinical candidates encompassing a broad spectrum of biological activities.
Herein, the synthesis a novel series of 3-aryl-3-arylmethoxyazetidines is described. Selected 3-aryl-3-arylmethoxyazetidines were evaluated for their binding affinity to multiple monoaminergic transporters for the potential treatment of methamphetamine addiction. It was discovered that this scaffold exhibits high binding affinity (nM) for both the serotonin and dopamine transporters. In addition, a new method was developed for the synthesis of 3,3-diarylazetidines. This new approach provides a facile and efficient method to synthesize a variety of diaryl heterocycles including 3,3-diarylazetidines, 3,3-diarylpyrrolidines, and 4,4-diarylpiperidines in moderate to good yields.
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Kloesges, Johannes. "Novel Chemistry of aziridines and azetidines." Thesis, University of Oxford, 2009. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.509969.
Pancholi, Alpa Kishor. "Synthesis of substituted azetidines and spirocyclic diazetidines." Thesis, University of Warwick, 2017. http://wrap.warwick.ac.uk/102606/.
Chapter 1 begins with an introduction to azetidines, including a discussion of the methodologies for their synthesis, their applications, relevance in natural products and as building blocks in medicinal chemistry. It then describes the development of a new asymmetric route to 2-substituted azetidin-3-ones using Enders’ SAMP/RAMP auxiliary. A one-pot process was developed involving the metalation of SAMP hydrazones of N-Boc-azetidin-3-one, alkylation and subsequent in situ hydrolysis to give the substituted products. Various bases and reaction conditions were explored to find optimal conditions for maximal yield and enantioselectivity. A representative range of electrophiles were screened including alkyl, allyl and benzyl halides and carbonyl compounds, producing enantioselectivities of up to 85% ee. Multiple substitution on the azetidin-3-one ring was briefly explored by repetition of the alkylation/hydrolysis sequence. Derivitisation by way of Pictet-Spengler reactions was used to confirm the absolute configuration at the newly created stereocentre. Chapter 2 begins with an introduction to 1,2-diazetidines outlining methods for their synthesis, before introducing the relevance of these nitrogen spirocycles. This chapter then describes two routes for the synthesis of these novel spirocyclic 1,2- diazetidines by (i) formation of the diazetidine ring and (ii) functionalisation of a range of 3-methylene-1,2-diazetidines including differentially protected variants. The diazetidines were subjected to dichloro- and difluorocyclopropanation with the latter achieved in high yields. Additionally, reactions with tetracyanoethylene by way of highly asynchronous [2π+2π] cycloadditions proceeded in near quantitative yield. In this way, a range of novel 4,5-diazaspiro[2.3]hexane and 1,2- diazaspiro[3.3]heptane spirocycles were produced. Chapter 3 details the experimental procedure and characterisation for all the novel compounds synthesised.
Khlebnikov, Alexander F., and Mikhail S. Novikov. "Ring Expansions of Azirines and Azetines." In Topics in Heterocyclic Chemistry, 143–232. Cham: Springer International Publishing, 2015. http://dx.doi.org/10.1007/7081_2015_154.
Moore, James A., and Rita Seelig Ayers. "Azetidines." In Chemistry of Heterocyclic Compounds: A Series Of Monographs, 1–217. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2008. http://dx.doi.org/10.1002/9780470187197.ch1.
Li, Jie Jack, and Minmin Yang. "Azetidines." In Drug Discovery with Privileged Building Blocks, 29–32. Boca Raton: CRC Press, 2021. http://dx.doi.org/10.1201/9781003190806-3.
Couty, François, and Olivier R. P. David. "Ring Expansions of Nonactivated Aziridines and Azetidines." In Topics in Heterocyclic Chemistry, 1–47. Cham: Springer International Publishing, 2015. http://dx.doi.org/10.1007/7081_2015_146.
Ghorai, Manas K., Aditya Bhattacharyya, Subhomoy Das, and Navya Chauhan. "Ring Expansions of Activated Aziridines and Azetidines." In Topics in Heterocyclic Chemistry, 49–142. Cham: Springer International Publishing, 2015. http://dx.doi.org/10.1007/7081_2015_159.
Beatriz, Adilson, Mirta Gladis Mondino, and Dênis Pires de Lima. "Lactams, Azetidines, Penicillins, and Cephalosporins: An Overview on the Synthesis and Their Antibacterial Activity." In N-Heterocycles, 97–142. Singapore: Springer Nature Singapore, 2022. http://dx.doi.org/10.1007/978-981-19-0832-3_3.
Singh, G. S., M. D’hooghe, and N. De Kimpe. "Azetidines, Azetines and Azetes: Monocyclic." In Comprehensive Heterocyclic Chemistry III, 1–110. Elsevier, 2008. http://dx.doi.org/10.1016/b978-008044992-0.00201-7.
de Kimpe, Norbert. "Azetidines, Azetines, and Azetes: Monocyclic." In Comprehensive Heterocyclic Chemistry II, 507–89. Elsevier, 1996. http://dx.doi.org/10.1016/b978-008096518-5.00018-6.
Andresini, Michael, Leonardo Degennaro, and Renzo Luisi. "Azetidines, Azetines and Azetes: Monocyclic." In Reference Module in Chemistry, Molecular Sciences and Chemical Engineering. Elsevier, 2021. http://dx.doi.org/10.1016/b978-0-12-818655-8.00155-4.
Mehta, L. K., and J. Parrick. "Other Fused Azetidines, Azetines and Azetes." In Comprehensive Heterocyclic Chemistry III, 239–319. Elsevier, 2008. http://dx.doi.org/10.1016/b978-008044992-0.00204-2.
Kaufman, Teodoro, and Marcela Amongero. "ORGANOCATALYTIC APPROACH TO THE SYNTHESIS OF OPTICALLY ACTIVE 1,2,3-TRISUBSTITUTED AZETIDINES." In The 13th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2009. http://dx.doi.org/10.3390/ecsoc-13-00211.
