Tesi sul tema "Diels-Alder cycloaddition reactions"
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Chumachenko, Natasha. "[Beta]-acryloyloxysulfonyl tethers for intramolecular Diels-Alder cycloaddition reactions". [Kent, Ohio] : Kent State University, 2005. http://rave.ohiolink.edu/etdc/view?acc%5Fnum=kent1135392557.
Testo completoTitle from PDF t.p. (viewed July 28, 2005). Author's first name appears on the abstract page as: Nataliya. Advisor: Paul Sampson. Keywords: b-hydroxysulfones; [beta]-hydroxysulfones; epoxide opening; intramolecular Diels-Alder reaction; vinylsulfones. Includes bibliographical references (p.194- 202).
Chumachenko, Nataliya. "b-Acryloyloxysulfonyl Tethers for Intramolecular Diels-Alder Cycloaddition Reactions". Kent State University / OhioLINK, 2005. http://rave.ohiolink.edu/etdc/view?acc_num=kent1135392557.
Testo completoShengxian, Zhao. "Cycloaddition reactions of meso-tetraarylporphyrins". Doctoral thesis, Universidade de Aveiro, 2005. http://hdl.handle.net/10773/4871.
Testo completoO trabalho apresentado nesta dissertação descreve o comportamento de meso-tetra-arilporfirinas em reacções de ciclo-adição e suas possíveis aplicações na síntese de novas porfirinas com grupos policíclicos aromáticos (“π-extended porphyrins”). No capítulo 1 apresenta-se uma revisão das aplicações de porfirinas e compostos afins e também das reacções de ciclo-adição que envolvem ligações duplas (periféricas) do macrociclo. O capítulo 2 descreve o trabalho feito em reacções de cicloadição 1,3-dipolar de meso-tetra-arilporfirinas com iletos de azometino. Considerou-se primeiramente a reactividade de meso-tetra-arilporfirinas simétricas perante iletos de azometino. Em seguida estudaram-se as reacções de meso-tetra-arilporfirinas de tipo A3B também com iletos de azometino. Seguidamente consideraram-se estudos similares mas desta vez visando reacções de cicloadição 1,3-dipolar, intramolecular, com meso-(o-formilfenil)porfirinas. O capítulo 3 descreve os estudos efectuados sobre transformações de Diels-Alder de meso-tetra-arilporfirinas com orto-quinodimetano de tipo pirazínico. Os novos produtos (“π-extended porphyrins”) obtiveram-se por ciclização intramolecular entre grupos meso-arilo e o anel quinoxalínico fundido em β. No capítulo 4 descrevem-se os estudos de ciclo-adição 1,3-dipolar de iletos N-piridínicos contendo o macrociclo porfirínico. As reacções de tais iletos com quinonas e com acetilenodicarboxilato de dimetilo originaram porfirinas subsituidas em posição meso com grupos de tipo indolizina. Essas quinonas foram usadas em excesso, actuando como dipolarófilos iniciais e depois como oxidantes. Obtiveram-se novos compostos aromáticos policíclicos nas reacções daqueles iletos com alcenos electronicamente deficientes e na ausência de oxidante. O capítulo 5 relata os resultados dos estudos de síntese de porfirinas com grupos policíclicos aromáticos através de reacções electrocíclicas. Isso foi conseguido a partir das reacções de porfirinas contendo grupos cetónicos com iletos de fósforo. A caracterização estrutural destes novos derivados fez-se recorrendo ao uso de técnicas espectroscópicas modernas, especialmente através de estudos de RMN. Estes métodos de RMN incluíram métodos mono e bidimensionais (1D: 1H, 13C, DEPT; 2D: COSY, NOESY, HSQC, HMBC).
The work presented in this dissertation describes the cycloaddition reaction studies concerning meso-tetraarylporphyrins and also their applications in the synthesis of novel π-extended porphyrins. Chapter 1 is a review on the applications of porphyrin derivatives and also on the cycloaddition reactions involving the peripheral double bonds of porphyrins. Chapter 2 is related with the 1,3-dipolar cycloaddition reactions of meso-tetraarylporphyrins with azomethine ylides. Firstly, the reactivities of symmetrical meso-tetraarylporphyrins in the reactions with azomethine ylides were investigated; secondly, the 1,3-dipolar cycloaddition reactions of A3B type meso-tetraarylporphyrins with azomethine ylides were also carried out; thirdly, the intramolecular 1,3-dipolar cycloaddition reactions of meso-(o-formylphenyl)porphyrins were also studied. Chapter 3 is related with Diels-Alder reactions of meso-tetraarylporphyrins with pyrazine ortho-quinodimethane. The novel π-extended porphyrins were obtained from the intramolecular ring closure reactions between the meso-aryl group and the β-fused quinoxaline ring. Chapter 4 is related with 1,3-dipolar cycloaddition reactions of porphyrinic pyridinium N-ylides. The reactions of porphyrinic pyridinium N-ylides with quinones and dimethyl acetylenedicarboxylate afford meso-substituted indolizine porphyrins. The quinones were used in excess, acting as dipolarophiles and as oxidants. The novel polycyclic aromatic compounds were obtained from the reactions of porphyrinic pyridinium N-ylides with the electron-deficient alkenes in the absence of any oxidant. Chapter 5 is related with the synthesis of polycyclic aromatic porphyrin analogues via electrocyclic reactions.These novel analogues were synthesized from the reactions of ketone-bridged porphyrins with phosphorus ylides. For the structural characterizations of the new compounds modern analytical techniques were used, with a special emphasis on NMR spectroscopic studies. These NMR methods include 1D: 1H, 13C, DEPT; 2D: COSY, NOESY, HSQC, HMBC.
MacNevin, Christopher J. "Reactivity of substituted 4-Pyridones in normal and inverse demand Diels-Alder cycloaddition /". Electronic version (PDF), 2003. http://dl.uncw.edu/etd/2003/macnevinc/christophermacnevin.pdf.
Testo completoNagare, A. S. "Physical - organic aspects of diels - alder reactions in eutectic and other environmental benign media". Thesis(Ph.D.), CSIR-National Chemical Laboratory, Pune, 2016. http://dspace.ncl.res.in:8080/xmlui/handle/20.500.12252/5884.
Testo completoCompain-Batissou, Cudel Muriel. "SYNTHESE DE NOUVELLES QUINONES HETEROCYCLIQUES PAR APPLICATION DES REACTIONS DE CYCLOADDITIONS DE DIELS-ALDER ET 1,3-DIPOLAIRE. EVALUATION IN VITRO DE LEUR ACTIVITE SUR TOXOPLASMA GONDII". Phd thesis, Université Claude Bernard - Lyon I, 2007. http://tel.archives-ouvertes.fr/tel-00281991.
Testo completoBanert, Klaus, Sandra Bochmann, Andreas Ihle, Oliver Plefka, Florian Taubert, Tina Walther, Marcus Korb, Tobias Rüffer e Heinrich Lang. "Synthesis with Perfect Atom Economy: Generation of Furan Derivatives by 1,3-Dipolar Cycloaddition of Acetylenedicarboxylates at Cyclooctynes". Universitätsbibliothek Chemnitz, 2014. http://nbn-resolving.de/urn:nbn:de:bsz:ch1-qucosa-152891.
Testo completoAlves, Jessica. "Advanced photochemical reaction systems for molecular design". Thesis, Queensland University of Technology, 2022. https://eprints.qut.edu.au/227734/1/Jessica_Alves_Thesis.pdf.
Testo completoBennes, Raphael Michel. "Recognition-induced control and acceleration of Diels-Alder cycloadditions". Thesis, University of Birmingham, 2000. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.368517.
Testo completoWijnen, Jan Willem. "Cycloadditions in aqueous media". [S.l. : [Groningen] : s.n.] ; [University Library Groningen] [Host], 1997. http://irs.ub.rug.nl/ppn/159343356.
Testo completoPepper, Adrian Gordon. "Asymmetric synthesis using acyl-nitroso cycloadditions : applications to natural product synthesis". Thesis, University of Salford, 2000. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.314011.
Testo completoSchmitt, Gérard. "Réactions de l'hydrofluoroborate d'un composé de Reissert sur divers alcenes : Compétition entre cycloaddition dipolaire-1,3 et cycloaddition de Diels-Alder". Besançon, 1987. http://www.theses.fr/1987BESA2041.
Testo completoWeisbrod, Samuel Hieronymus [Verfasser]. "Catalyst-free chemoselective DNA conjugation by the Staudinger ligation and Diels Alder cycloaddition reaction / Samuel Hieronymus Weisbrod". Konstanz : Bibliothek der Universität Konstanz, 2010. http://d-nb.info/1022323741/34.
Testo completoSancibrao, Pierre. "Cycloadditions de nitroso Diels-Alder asymétriques et régiosélectives : une nouvelle voie synthétique d'hétérospirocycles". Thesis, Paris 11, 2012. http://www.theses.fr/2012PA112417.
Testo completoDuring this research, we were interested in the synthesis of enantiopur heterospiranic bicycles. We therefore developed a new synthetic route towards the synthesis of molecules with different spirocyclic structures. This novel synthetic route features a nitroso Diels-Alder cycloaddition as key step. The total control of the stereoselectivity and the regioselectivity of the reaction, rarely described in the literature, have been specifically studied during this work. This study allows us to have a better understanding of this reaction. Two different approaches have been developed in this work. They both led to total control of the regioselectivity of this cycloaddition. Cycloadditions performed by reactions using a nitrosopyridine dienophile and catalyzed by a chiral source of copper allows the synthesis of cycloadducts precursor of azaspirocycles with a modest enantioselectivity. Cycloadditions using a chloronitroso chiral dienophile derived from xylose allowed the synthesis of oxaspiraniques precursors with enantioselective excess of at least 95%. The last approach was finally validated by the synthesis of various spiroethers and spirolactones through N-O bond cleavage an intramolecular cyclizations. Finally, the vinyl triflate function of the spirolactones and spiroethers was engaged in Suzuki couplings to introduce molecular diversity at a late stage allowing the synthesis of 9 different spiranic structures including 5 enantioenriched
Yu, Jianguo. "Novel chiral phosphonium ionic liquids as solvents and catalysts for cycloadditions : investigation of the Diels-Alder reaction of a series of dienes and dienophiles in novel chiral phosphonium ionic liquids". Thesis, University of Bradford, 2009. http://hdl.handle.net/10454/4307.
Testo completoChabour, Ihssene. "1,3-Dipolar cycloadditions using catalysts with double chirality and novel multicomponent [4+2] processes". Doctoral thesis, Universidad de Alicante, 2021. http://hdl.handle.net/10045/114674.
Testo completoSultan, Nisrine. "Preparations selectives de derives du 7-oxanorborna-2,5-diene : utilisation comme formes masquées de composés acetyleniques". Thesis, Paris 11, 2011. http://www.theses.fr/2011PA112132.
Testo completoIn order to selectively prepare heterocyclic compounds, a study of the synthesis and reactivity of 7-oxanorborna-2,5-dienes with different electron-withdrawing groups on the 2 and 3 positions was performed. These compounds are masked forms of unsymmetrical acetylenic compounds. At first, we have optimized a new method for the selective synthesis of unsymmetrical diesters by transesterification of symmetrical dialkyl acetylenedicarboxylates in the presence of Candida rugosa lipase. This unexpectedly highly selective method allowed us to obtain unsymmetrical acetylenedicarboxylates in good yields.In a second part, we have developed a regioselective synthesis of 7-oxanorborna-2,5-diene-2,3-dicarboxylic acid derivatives according to two strategies. In one approach, an intramolecular Diels-Alder reaction between a furan and an acetylenic compound connected by silicon-containing tethers was performed, followed by a cleavage of the Si-C bonds. This [4+2] cycloaddition was carried in the presence of a Lewis acid, only MeAlCl2 gave the expected product and so in moderate yields. In most cases, the cleavage of Si-C bonds leads to the desired diesters. In a second approach, a mono-saponification of dialkyl oxanorbornadiene-2,3-dicarboxylates provided access regioselectively to mono-acids and coupling reactions with amines or alcohols selectively led to poly-functionalized products containing two different electron-withdrawing groups.In the last part, we have regioselectively prepared 3-pyrrolines by [2+3] cycloaddition of an azomethine ylide to 7-oxanorbornadienes bearing electroattracting groups followed by a retro-Diels-Alder reaction. An easy synthesis of previously unknown condensed 3-pyrrolines was obtained by formation of an unexpected succinimide pattern from amidoesters. In conclusion, it appears that the presence of an ethyl group on the bridgehead carbon atom of 7-oxanorborna-2,5-dienes seems sufficient to control the regioselectivity of these cycloadditions
Filho, Luiz Carlos da Silva. "Pentacloreto de nióbio como ácido de Lewis em reações de cicloadição [2+2] e [4+2]". Universidade de São Paulo, 2006. http://www.teses.usp.br/teses/disponiveis/59/59138/tde-22122006-124222/.
Testo completoThe aim of this work was to investigate the use of NbCl5 as Lewis acid in cycloadittion reactions. We have studied [2 + 2] cycloaddition reactions, Diels-Alder reactions between enonas and cyclopentadiene and aza-Diels-Alder reactions with Schiff bases. The effects of the temperature and of the molar concentration of NbCl5 were also evaluated. Comparasion of reaction yields, obtained products as well as reation time with NbCl5 were also a key point on this work. The [2 + 2] cycloaddition reactions were performed using propiolic ester and different types of alkenes (silyl enol ethers and aliphatic alkenes). In the reactions with silyl enol ethers, formation of the corresponding cyclobutene aductts was not verified, since the NbCl5 promotes the rupture of oxygen-silicon bonds, and the desired product is not obtained. In the reactions with aliphatic alkenes, it was possible to obtain the adduct, however, in lower yields as compared to those obtained with others Lewis acids. Regarding the Diels-Alder reactions, we have investigated reactions using different cycloenones (dienophiles of low reactivity) with cyclopentadiene (diene) with NbCl5. The obtained results indicate that NbCl5 is a good Lewis acid to activate these Diels-Alder reactions, resulting in shorter reaction times and higher diastereoselectivity at lower temperatures than other Lewis acids. The possibility of carrying out Diels-Alder reaction at -78 0C is another remarkable aspect of this work. Besides demonstrating the strong activation of the enone system by NbCl5, it opens the possibility of obtaining high stereoselectivity. We have also performed studies of complete structural elucidation of some compounds by using different NMR techniques (uni and bidimensional), with the help of theoretical calculations. In the aza-Diels-Alder reactions between Schiff bases and dihydropyran, the NbCl5 was an excellent catalyst for the synthesis of pyranoquinoline derivatives. These derivatives are an importante class of natural products that exhibit wide range of biological activity. The reactions were carried out at low concentration of niobium and in relatively short times, resulting in yields varying from 72 to 96 %. Another aspect that should be remarked is the high diastereoselectivity found in these reactions. We have also carried out studies of tripanocydal activity of pyranoquinoline derivatives prepared through aza-Diels-Alder reactions catalyzed by NbCl5.
Duflos, Jack. "Synthèse et réactions de cycloadditions sur des systèmes pyrroliques à noyaux condensés". Rouen, 1987. http://www.theses.fr/1987ROUES003.
Testo completoFerroud, Clotilde. "Étude de la réaction de Diels-Adler intra et intermoléculaire sous haute pression : application à la synthèse stéréosélective d'alcaloïdes de l'indole du groupe des yohimbanes". Paris 6, 1986. http://www.theses.fr/1986PA066023.
Testo completo(14010168), Mirta Golic. "The preparation of dienes and dienophiles containing nucleic acid bases". Thesis, 1999. https://figshare.com/articles/thesis/The_preparation_of_dienes_and_dienophiles_containing_nucleic_acid_bases/21397758.
Testo completoThe work presented in this thesis deals initially with the synthesis of rigid polyalicyclic dienes and dienophiles with pyrimidine moieties inbuilt in a rigid fashion (building BLOCKS). This work has allowed the production of a new class of ribbon molecules with precisely defined size, shape and position of the pyrimidine ring. In the second stage of the project, an assessment of their ability to participate in cycloaddition reactions as pyrimidine building BLOCK* components was investigated.
2,4-Dimethoxy-1,3-diazaanthracene (I) has acted as the pyrimidine transfer reagent for preparing building BLOCKs. The Diels-Alder adducts IV and V (Scheme I), prepared by reaction of I with norbomadiene, are new pyrimidine dienophilic BLOCKs. Both I and 2,4-dichloro-1,3-diazaanthracene (II) were active in photochemical [4π+4π] cycloaddition reactions with cyclopentadiene to form a second class of building BLOCKs VII and VIII (Scheme I). In addition, the photodimerisation of I and II was studied and structures IX-XII assigned on the basis of spectral and X-ray method.
The 2,4-dichloro-photoadduct VIII is of particular importance for this work since it is easily hydrolysed (2M NaOH, 60 °C, overnight) to the corresponding uracil XIII In contrast, thermal adducts IV and V were very difficult to hydrolyse (NaOH fusion) to uracils XIV and XV (Figure I).
The availability of pyrimidine BLOCKs which contain a reactive π-bond, e.g. (IV, V, VII and VIII) has enabled us to employ 3,6-di(2'-pyridyl)-s-tetrazine (XVI) and ACE (Alkene plus Cyclobutene Epoxide) coupling methods to obtain precisely functionalised ribbon molecules in a direct, convergent synthetic strategy.
The synthesis of the bis-pyrimidines by coupling norbornene reagents using 3,6-di(2'-pyridyl)-s-tetrazine is illustrated in Scheme II. In the first step, s-tetrazine XVI was reacted with pyrimidine BLOCK V under basic conditions to generate the dihydropyridazine XVII. This diaza-1,3-diene was reacted with a further equivalent of V under high pressure conditions to yield the bis-pyrimidines XVIII and XIX, which were separated by radial chromatography. The same procedure was used to link pyrimiclines to other effectors by using alternative alkenes in the second step.
The ACE coupling protocol is illustrated by the reaction of alkene VIII with the dimethoxynaphthalene-containing epoxide XX (Scheme III). The reaction can be conducted under thermal or photochemical conditions and is considered to proceed via 1,3-dipolar intermediate formed by ring-opening of the epoxide C-C bond of XX (See Chapter 4).
Each class of coupled adduct could be hydrolysed to the corresponding uracil by using either acid (XXII) or base (XXIII) hydrolysis conditions, the choice depending on the structure of the molecule in question and its substituents.
The work presented in this thesis involves a deal of new work and has been instrumental in the development of the Lego®-based BLOCK assembly protocol for ribbon molecules construction.
Lording, William James. "A deeper understanding of the Diels–Alder reaction". Phd thesis, 2010. http://hdl.handle.net/1885/11776.
Testo completoChen, Shang-Hong, e 陳尚鴻. "1. Approach to the kempane skeleton via intramolecular Diels-Alder cycloaddition of fulvene 2. Application of organocatalysts in Baylis-Hillman reaction and related cycloaddition". Thesis, 2006. http://ndltd.ncl.edu.tw/handle/51860899827903256040.
Testo completo國立中正大學
化學所
94
Part 1: Approach to the kempane skeleton via intramolecular Diels-Alder cycloaddition of fulvene The Kempane skeletons can be prepared rapidly via intramolecular Diels-Alder cycloadditions (IMDA) of fulvenes. The chemistry upon both intramolecular Diels-Alder cycloadditions and Prins reaction. Part 2: Application of organocatalysts in Baylis-Hillman reaction and related cycloaddition A highly enantioselective proline catalyzed intramolecular Baylis–Hillman reaction of hept-2-enedial is reported. Addition of imidazole to the mixture results in an unusual inversion of enantioselectivity. The organocatalyzed [3 + 3] and [4+2] cycloaddition of ?β-unsaturated aldehydes affored aromatic aldehydes.