Academic literature on the topic 'Pyrrole derive'
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Journal articles on the topic "Pyrrole derive"
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Cordero, Franca, Bhushan Khairnar, Anna Ranzenigo, and Alberto Brandi. "Cycloaddition of Benzyne with Alkoxy-Substituted Pyrroline-N-oxides: Unexpected Rearrangement to an N-Phenylpyrrole." SynOpen 02, no. 01 (January 2018): 0025–29. http://dx.doi.org/10.1055/s-0037-1609082.
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Reaction of enantiopure 3,4-dialkoxy-pyrroline N-oxides with benzyne affords the expected tetrahydrobenzo[d]pyrrolo[1,2-b]isoxazoles along with an unexpected 2,3-disubstitued-N-phenyl-pyrrole derived from an unprecedented rearrangement of the adduct of nitrone with two molecules of benzyne. A mechanism for the unusual rearrangement is proposed. The benzo[d]isoxazolidine derivatives are conveniently converted into 2-(2-hydroxyphenyl)-3,4-dialkoxypyrrolidines by reductive opening of the N–O bond.
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Hu, Nan, Li Jun He, and Li Hui Wang. "Study on Surface Chemical Composition and Structure of PVP/Al Composite Powder Using XPS Analysis." Advanced Materials Research 476-478 (February 2012): 1101–4. http://dx.doi.org/10.4028/www.scientific.net/amr.476-478.1101.
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XPS analysis is used in studying surface chemical composition and structure of ultrafine raw Al powder and PVP/Al composite powder, respectively. It shows that: in PVP/Al composite powder’s surface, comparing with raw Al powder, relative content of Al decrease and relative contents of C and N increase. New chemical bonds are formed in PVP/Al composite powder’s surface, and it is certain that, these new chemical bonds derive from N atom and O atom of PVP’s pyrrole with Al atom in Al powder surface.
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Bi, Wenzhao, Geeng-Fu Jang, Lei Zhang, John W. Crabb, James Laird, Mikhail Linetsky, and Robert G. Salomon. "The Adductomics of Isolevuglandins: Oxidation of IsoLG Pyrrole Intermediates Generates Pyrrole–Pyrrole Crosslinks and Lactams." High-Throughput 8, no. 2 (May 10, 2019): 12. http://dx.doi.org/10.3390/ht8020012.
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Isoprostane endoperoxides generated by free radical-induced oxidation of arachidonates, and prostaglandin endoperoxides generated through enzymatic cyclooxygenation of arachidonate, rearrange nonenzymatically to isoprostanes and a family of stereo and structurally isomeric γ-ketoaldehyde seco-isoprostanes, collectively known as isolevuglandins (isoLGs). IsoLGs are stealthy toxins, and free isoLGs are not detected in vivo. Rather, covalent adducts are found to incorporate lysyl ε-amino residues of proteins or ethanolamino residues of phospholipids. In vitro studies have revealed that adduction occurs within seconds and is uniquely prone to cause protein–protein crosslinks. IsoLGs accelerate the formation of the type of amyloid beta oligomers that have been associated with neurotoxicity. Under air, isoLG-derived pyrroles generated initially are readily oxidized to lactams and undergo rapid oxidative coupling to pyrrole–pyrrole crosslinked dimers, and to more highly oxygenated derivatives of those dimers. We have now found that pure isoLG-derived pyrroles, which can be generated under anoxic conditions, do not readily undergo oxidative coupling. Rather, dimer formation only occurs after an induction period by an autocatalytic oxidative coupling. The stable free-radical TEMPO abolishes the induction period, catalyzing rapid oxidative coupling. The amine N-oxide TMAO is similarly effective in catalyzing the oxidative coupling of isoLG pyrroles. N-acetylcysteine abolishes the generation of pyrrole–pyrrole crosslinks. Instead pyrrole-cysteine adducts are produced. Two unified single-electron transfer mechanisms are proposed for crosslink and pyrrole-cysteine adduct formation from isoLG-pyrroles, as well as for their oxidation to lactams and hydroxylactams.
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Pravardhan Reddy, E., A. Sumankumar, B. Sridhar, Y. Hemasri, Y. Jayaprakash Rao, and B. V. Subba Reddy. "1,5-Electrocyclization of conjugated azomethine ylides derived from 3-formyl chromene and N-alkyl amino acids/esters." Organic & Biomolecular Chemistry 15, no. 36 (2017): 7580–83. http://dx.doi.org/10.1039/c7ob00705a.
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A novel strategy has been developed for the synthesis of chromeno[3,4-b]pyrrol-4(3H)-one and substituted pyrrole derivatives. This is the first example of the preparation of highly substituted pyrrole derivatives from chromene-3-carboxaldehydes.
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Allen, Annette D., Jean-Marc Kwong-Chip, Wing Cheung Lin, Paul Nguyen, and Thomas T. Tidwell. "Formation and reactivity of 1-pyrrolyl-2,2,2-trifluoroethyl cations." Canadian Journal of Chemistry 68, no. 10 (October 1, 1990): 1709–13. http://dx.doi.org/10.1139/v90-265.
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1-(1-Methyl-2-pyrrolyl)-2,2,2-trifluoroethyl p-nitrobenzoate (3) reacts by carbocation formation with an m value for the dependence of rate on the solvent polarity parameter YOTs of 0.56, and a rate 41 times slower than (1-methyl-2-pyrrolyl)methyl p-nitrobenzoate. The products from 3 include significant amounts of material derived from solvent attack at the 5-position of the pyrrole ring. The results indicate a high degree of charge delocalization by the strongly donating pyrrolyl group, resulting in a low k(H)/k(CF3) rate ratio and nucleophilic attack on the ring. 1,1, l-Trifluoro-2-(1-methyl-2-pyrrolyl)propan-2-ol (10) reacted with CF3CO2H via a tertiary carbocation, which led to dimeric products resulting from electrophilic substitution on the pyrrole ring. Keywords: pyrrole, trifluoromethyl substituents, carbocations.
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Bagherzadeh, Mojtaba, Mohammad Adineh Jonaghani, Mojtaba Amini, and Anahita Mortazavi-Manesh. "Synthesis of dipyroromethanes in water and investigation of electronic and steric effects in efficiency of olefin epoxidation by sodium periodate catalyzed by manganese tetraaryl andtransdisubstituted porphyrin complexes." Journal of Porphyrins and Phthalocyanines 23, no. 06 (May 28, 2019): 671–78. http://dx.doi.org/10.1142/s108842461950038x.
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Condensation of pyrrole with various aldehydes in the presence of BF3•etherate as an acid catalyst in water provides good yield of some dipyrromethanes. Prolongation of the reaction time with aldehydes substituted by electron-donating (mesityl) or electron-withdrawing (2,6-dichlorophenyl) groups on the ortho positions of the phenyl did not lead to decomposition or scrambling. Manganese trans disubstituted porphyrin complexes which derive from various dipyrromethanes and manganese tetraaryl porphyrin complexes including various substituents with different steric and electronic properties show good catalytic activity in epoxidation of alkenes by NaIO4in the presence of imidazole (ImH). The study of steric and electronic effects of the catalysts on the epoxidation of olefins shows that Mn-porphyrin complexes with more bulky and electron-releasing groups on meso phenyls could increase the epoxidation yield of most alkenes.
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Huang, Wenbo, Kaimei Wang, Ping Liu, Minghao Li, Shaoyong Ke, and Yanlong Gu. "Three-component reactions of aromatic amines, 1,3-dicarbonyl compounds, and α-bromoacetaldehyde acetal to access N-(hetero)aryl-4,5-unsubstituted pyrroles." Beilstein Journal of Organic Chemistry 16 (November 30, 2020): 2920–28. http://dx.doi.org/10.3762/bjoc.16.241.
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N-(Hetero)aryl-4,5-unsubstituted pyrroles were synthesized from (hetero)arylamines, 1,3-dicarbonyl compounds, and α-bromoacetaldehyde acetal by using aluminum(III) chloride as a Lewis acid catalyst through [1 + 2 + 2] annulation. This new versatile methodology provides a wide scope for the synthesis of different functional N-(hetero)aryl-4,5-unsubstituted pyrrole scaffolds, which can be further derived to access multisubstituted pyrrole-3-carboxamides. In the presence of 1.2 equiv of KI, a polysubstituted pyrazolo[3,4-b]pyridine derivative was also successfully synthesized.
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Cozzi, Pier Giorgio, Sandro Gambarotta, Magda Monari, and Luca Zoli. "Convenient Preparation of Chiral Dipyrrolylmethanes Containing a Chiral Moiety." Collection of Czechoslovak Chemical Communications 72, no. 8 (2007): 1046–56. http://dx.doi.org/10.1135/cccc20071046.
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A variety of chiral bis-pyrroles have been made readily accessible via acid-catalyzed condensation of chiral ketones with pyrrole. Three representative chiral ketones 2-4 taken from the chiral pool were transformed into the corresponding bis-pyrrole derivatives in a straightforward acid-catalyzed condensation. Chiral β-hydroxy ketone derivatives, prepared through proline-catalyzed aldol condensation of acetone and an aldehyde, are readily transformed into the corresponding dipyrrolylmethane by the acid-catalyzed condensation carried out in the same conditions. The crystal structure of the chiral dipyrrolylmethane 2 derived from the (-)-menthone was determined.
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El Gamal, Abrahim, Vinayak Agarwal, Stefan Diethelm, Imran Rahman, Michelle A. Schorn, Jennifer M. Sneed, Gordon V. Louie, et al. "Biosynthesis of coral settlement cue tetrabromopyrrole in marine bacteria by a uniquely adapted brominase–thioesterase enzyme pair." Proceedings of the National Academy of Sciences 113, no. 14 (March 21, 2016): 3797–802. http://dx.doi.org/10.1073/pnas.1519695113.
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Halogenated pyrroles (halopyrroles) are common chemical moieties found in bioactive bacterial natural products. The halopyrrole moieties of mono- and dihalopyrrole-containing compounds arise from a conserved mechanism in which a proline-derived pyrrolyl group bound to a carrier protein is first halogenated and then elaborated by peptidic or polyketide extensions. This paradigm is broken during the marine pseudoalteromonad bacterial biosynthesis of the coral larval settlement cue tetrabromopyrrole (1), which arises from the substitution of the proline-derived carboxylate by a bromine atom. To understand the molecular basis for decarboxylative bromination in the biosynthesis of 1, we sequenced two Pseudoalteromonas genomes and identified a conserved four-gene locus encoding the enzymes involved in its complete biosynthesis. Through total in vitro reconstitution of the biosynthesis of 1 using purified enzymes and biochemical interrogation of individual biochemical steps, we show that all four bromine atoms in 1 are installed by the action of a single flavin-dependent halogenase: Bmp2. Tetrabromination of the pyrrole induces a thioesterase-mediated offloading reaction from the carrier protein and activates the biosynthetic intermediate for decarboxylation. Insights into the tetrabrominating activity of Bmp2 were obtained from the high-resolution crystal structure of the halogenase contrasted against structurally homologous halogenase Mpy16 that forms only a dihalogenated pyrrole in marinopyrrole biosynthesis. Structure-guided mutagenesis of the proposed substrate-binding pocket of Bmp2 led to a reduction in the degree of halogenation catalyzed. Our study provides a biogenetic basis for the biosynthesis of 1 and sets a firm foundation for querying the biosynthetic potential for the production of 1 in marine (meta)genomes.
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Ning, Jia, Ivonne M. C. M. Rietjens, and Marije Strikwold. "Integrating physiologically based kinetic (PBK) and Monte Carlo modelling to predict inter-individual and inter-ethnic variation in bioactivation and liver toxicity of lasiocarpine." Archives of Toxicology 93, no. 10 (September 11, 2019): 2943–60. http://dx.doi.org/10.1007/s00204-019-02563-x.
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Abstract The aim of the present study was to predict the effect of inter-individual and inter-ethnic human kinetic variation on the sensitivity towards acute liver toxicity of lasiocarpine in the Chinese and the Caucasian population, and to derive chemical specific adjustment factors (CSAFs) by integrating variation in the in vitro kinetic constants Vmax and Km, physiologically based kinetic (PBK) modelling and Monte Carlo simulation. CSAFs were derived covering the 90th and 99th percentile of the population distribution of pyrrole glutathione adduct (7-GS-DHP) formation, reflecting bioactivation. The results revealed that in the Chinese population, as compared to the Caucasian population, the predicted 7-GS-DHP formation at the geometric mean, the 90th and the 99th percentile were 2.1-, 3.3- and 4.3-fold lower respectively. The CSAFs obtained using the 99th percentile values were 8.3, 17.0 and 19.5 in the Chinese, the Caucasian population and the two populations combined, respectively, while the CSAFs were generally 3.0-fold lower at the 90th percentile. These results indicate that when considering the formation of 7-GS-DHP the Caucasian population may be more sensitive towards acute liver toxicity of lasiocarpine, and further point out that the default safety factor of 3.16 for inter-individual human kinetic differences may not be sufficiently protective. Altogether, the results obtained demonstrate that integrating PBK modelling with Monte Carlo simulations using human in vitro data is a powerful strategy to quantify inter-individual variations in kinetics, and can be used to refine the human risk assessment of pyrrolizidine alkaloids.
Dissertations / Theses on the topic "Pyrrole derive"
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Torres, Rodriguez Luz Maria. "Synthèses et caractérisations électrochimiques de films de polypyrrole fonctionnalisés par des unités biotine : étude de la reconnaissance biotine/avidine." Université Joseph Fourier (Grenoble), 2000. http://www.theses.fr/2000GRE10189.
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Ce travail decrit l'elaboration et la caracterisation d'un biocapteur compose d'une matrice polymere, un polymere conducteur electronique le polypyrrole, incluant des molecules de biotine greffees par un lien covalente covalente au polypyrrole. Ce biocapteur est obtenu par electyropolymerisation de monomere pyrrole pre-fonctionnalise par des molecules de biotine. Nous presentons dans une premiere partie la synthese de deux monomeres biotinyles qui sont formes par une unite pyrrole lie a la biotine par l'intermediaire d'un bras espaceur polyether. Ces deux monomeres se differencient par la longueur du bras espaceur qui lie le pyrrole et l'unite biotine, respectivement notes $$1 et $$2 pour la molecule a bras court (14 atomes) et long (21 atomes). Dans la deuxieme partie du travail nous abordons la synthese et la caracterisation electrochimique des films biotinyles en milieu aqueux. Les films sont prepares soit par electrohomopolymerisation des monomeres $$1 et $$2, soit par electrocopolymerisation de $$1 avec du pyrrole ou un n-alkyle pyrrole qui se differencie du monomere $$1 seulement par la substitution de l'entite biotine par un groupement acetamide. Les resultats montrent que la reponse voltamperometrique des films poly$$1 et poly$$2 depend de l'epaisseur du film. En effet, pour des films minces (71 nm) la reponse presente deux pics anodiques tandis que pour films plus epais (242 nm) un seul pic anodique est observe. Ce comportement differe de la reponse electrochimique des autres n-alkyle pyrroles. Dans la derniere partie de ce travail l'immobilisation des molecules d'avidine a ete mise en evidence par microgravimetrie (microbalance a quartz) et voltamperometrie cyclique. D'apres les resultats obtenus par microgravimetrie la longueur du bras espaceur qui lie le pyrrole et l'unite biotine joue un role importante sur la quantite d'avidine immobilisee puisque sur le film poly$$2 deux fois plus de molecules d'avidine sont ancrees par rapport au film poly$$1. D'autre part nous avons montre que la reponse voltamperometrique de ces deux films poly$$1 et poly$$2 est modifiee par l'immobilisation de l'avidine.
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Berlot, Isabelle. "Synthèse, caractérisation et étude électrochimique de tensioactifs dérivés du pyrrole." Université Joseph Fourier (Grenoble), 1998. http://www.theses.fr/1998GRE10087.
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Ce memoire est consacre a la synthese, la caracterisation et l'etude electrochimique de nouveaux tensioactifs derives du pyrrole, analogues du dodecyltrimethylammonium et associes aux contre-ions br#-, no#-#3, tso#-, bf#-#4. La plupart forment des micelles en solution aqueuse. Une electrode selective du cation dodecyltrimethylammonium a ete utilisee pour determiner leurs concentrations micellaires critiques (cmc). Nous avons aussi montre que la voltammetrie cyclique permet dans certains cas de determiner la cmc en milieu electrolytique, en depit du caractere irreversible de l'oxydation de la sonde redox que constitue le pyrrole. On constate que l'introduction d'un motif pyrrole a l'extremite de la chaine hydrocarbonee (series a1 et a2) ne modifie pas la cmc de ces tensioactifs par rapport a leurs analogues sans pyrrole. Par contre si le pyrrole est situe sur la tete polaire (serie b1), leur cmc est plus basse. L'etude par rmn#1h a eclaire ces constatations, en precisant la localisation des divers groupements dans la micelle : le pyrrole se place dans le cur hydrophobe dans le cas des a1 et a2, alors qu'il se replie vers l'interieur de la micelle pres de la tete polaire pour les b1. Dans le cas particulier des tensioactifs associes a l'anion tosylate, nous avons constate que le tosylate penetre dans la micelle et s'intercale entre les groupes ammonium. L'etude electroanalytique a montre que ces composes s'adsorbent fortement sur carbone et que des films de polypyrrole peuvent croitre sur ces electrodes par electrooxydation de solutions micellaires. Ces films sont electroinactifs, mais d'epaisseurs significatives (20 a 1000 couches monomoleculaires). Les rendements de depots sont faibles (5 a 10%) dans le cas des a1 et a2, mais nettement plus importants (50%) dans le cas des b1. L'electropolymerisation de solutions micellaires des series a1 et a2 conduit majoritairement a la formation d'oligomeres solubles, de type polypyrrole suroxyde.
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Mailley, Pascal. "Immobilisation d'enzymes dans des poly(pyrrole-amphiphiles) : caractérisation et application à la biodétection ampérométrique du glucose." Université Joseph Fourier (Grenoble ; 1971-2015), 1995. http://www.theses.fr/1995GRE10160.
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Les biocapteurs amperometriques decrits dans ce travail sont des dispositifs analytiques bases sur l'immobilisation d'une enzyme a la surface d'une electrode. Les performances du biocapteur sont fortement conditionnees par la methode d'immobilisation mise en uvre ainsi que par les caracteristiques de la matrice hote qui en resulte. Dans ce contexte, ce travail developpe une nouvelle technique d'immobilisation electrochimique d'enzyme basee sur les proprietes remarquables d'une famille de derives n-substitues amphiphiles du pyrrole. Les tres larges potentialites de cette technique, qui fait appel a l'electropolymerisation d'un depot adherent d'enzyme et de monomere, ont ete demontrees pour une serie de cinq enzymes presentant des tailles et des points isoelectriques tres differents. Les performances analytiques des differents biocapteurs ont ete comparees et correlees a la permeabilite des matrices polymeres hotes. Le monomere presentant les meilleures potentialites (12-(pyrrol, yl)dodecyltriethylammonium) a ensuite ete applique a l'immobilisation de la glucose oxydase. Apres optimisation des parametres operationnels (temperature, ph,) et structuraux (composition du bio-materiau), les caracteristiques metrologiques des biocapteurs a la glucose ont ete modulees grace a l'elaboration de structures multicouches. Finalement, trois strategies, basees sur l'optimisation de la detection amperometrique ou sur l'utilisation de membranes semi-permeables, ont ete etudiees de maniere a augmenter la selectivite des biocapteurs au glucose vis-a-vis des interferents
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Sayah, Ghassemi Babak. "Chimie et réactivité des hexahydropyrroloindolizines : application à la synthèse des myrmicarines." Université Joseph Fourier (Grenoble), 2001. http://www.theses.fr/2001GRE10114.
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Parmi les composes naturels ou synthetiques possedant des activites biologiques interessantes, les alcaloides tiennent une part importante. Recemment une nouvelle famille d'alcaloides bicycliques et oligocycliques, nommee myrmicarine, a ete isolee de glandes a poisons de fourmis d'afrique de type mirmicinae. La plupart de ces composes possedent en totalite ou en partie un motif hexahydropyrroloindolizine contenant un centre stereogene dont la configuration absolue n'est pas connue. Nous avons entrepris la synthese de ces alcaloides sous forme enantiopure. Dans un premier temps, suivant une strategie divergente basee sur des reactions de substitution electrophile regioselective sur un noyau pyrrolique nous avons synthetise un motif hexahydropyrroloindolizinone sous forme enantiopure, et par la suite les myrmicarines 217 et 215 (a et b). Dans un deuxieme temps, nous avons etudie la regioselectivite des reactions d'acylation de type vilsmeier-haack sur le tricycle quasi-symetrique hexahydropyrroloindolizine. Des conditions ideales ont ete mises au point permettant une substitution electrophile regiospecifique. Cette etude a ouvert une deuxieme voie d'acces aux myrmicarines 217 et 215 (a et b). Enfin nous avons propose deux voies d'acces a la myrmicarine 430 dont une est basee sur l'auto condensation des myrmicarines 215 (a et b) et pourrait etre assimilee a une synthese biomimetique de cet alcaloide.
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Jouaiti, Abdelaziz. "Activation electrochimique de petites molecules par des composes bi-metalliques et elaboration de films polymeres conducteurs." Université Louis Pasteur (Strasbourg) (1971-2008), 1989. http://www.theses.fr/1989STR13036.
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Reduction electrocatalytique de co::(2) dans le dmf en presence de ni(cyclam)**(2+) (bis cyclam)**(4+). Modification d'electrodes par polymerisation electrolytique de differents complexes de fe ii, co ii et ru ii avec le coordinat (p-pyrrolylmethylphenyl)-4' terpyridine-2,2:6',2". Ce nouveau type d'electrodes peut jouer le role de mediateur redox
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Martre, Agnès. "Polymérisation par voie photochimique et électrochimique de complexes trisbipyridine de ruthénium(II) : application à des systèmes supramoléculaires à propriétés photorédox." Université Joseph Fourier (Grenoble), 1999. http://www.theses.fr/1999GRE10197.
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Ce memoire est consacre a l'elaboration de polymeres solubles supramoleculaires modeles du systeme photosynthetique naturel. Ces modeles sont prepares a partir de monomeres constitues d'un photosensibilisateur redox ru(bpy) 3 2 + lie de maniere covalente a des accepteurs d'electron (viologene) et a des groupes polymerisables (pyrrole). Les polymeres obtenus par voie electrochimique de ces systemes de type diade etant peu solubles, la polymerisation par voie photochimique a ete exploree. Tout d'abord, les conditions de formation, par irradiation lumineuse en presence d'accepteurs d'electron irreversibles, d'un polymere soluble a partir de complexes simples du type ru(bpy) 3 2 + substitues par une ou plusieurs chaines alkyle-pyrrole de longueur variable ont ete determinees ; l'oxygene moleculaire ou un sel de diazonium ont ete utilises comme accepteurs d'electron. L'influence de la longueur de la chaine alkyle, de la reticulation des polymeres et de la voie de polymerisation sur les proprietes electrochimiques et photophysiques de ces complexes a ete etudiee. L'examen des constantes photophysiques s'avere etre une source d'information sur la structure des polymeres. Il ressort, en particulier, que la nature du processus de polymerisation (photo- ou electropolymerisation) gouverne le nombre moyen d'unites monomere dans les polymeres. L'application de la photopolymerisation a des complexes de type diade a alors montre que la formation du polymere est fortement dependante de la distance entre le photosensibilisateur et le groupe pyrrole : une faible distance entre ces deux entites est indispensable. Par ailleurs, les proprietes de separation de charges photoinduite des diades sont conservees apres polymerisation. Enfin, ces polymeres peuvent s'adsorber de maniere stable lors de leur reduction a la surface d'une electrode, rendant possible leur utilisation en tant que materiaux d'electrode.
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Innocent, Christophe. "Immobilisation de biomolécules dans des polypyrroles fonctionnalisés : application à l'électroanalyse." Université Joseph Fourier (Grenoble ; 1971-2015), 1995. http://www.theses.fr/1995GRE10152.
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L'utilisation de monomeres pyrroliques fonctionnalises electropolymerisables afin d'immobiliser des biomolecules (enzymes, metabolites) a conduit a la creation de nouveaux biomateriaux d'electrode. Les proprietes d'echange d'anions des films de poly(pyrrole ammonium) et poly(pyrroles viologene) ont ete utilisees pour l'immobilisation et l'activation electrochimiques d'un coenzyme ainsi que pour l'incorporation et la liberation electrochimiquement controlee d'adenosine triphosphate et d'acide 3 ;4 dihydroxyphenylacetique. Une nouvelle technique d'immobilisation d'enzymes a partir de monomeres pyrroles ammoniums amphiphiles a ete developpee grace a leurs proprietes de dispersion, d'adsorption et d'electropolymerisation sous leur forme adsorbe en milieu aqueux. Ces biomateriaux d'electrode ont ete appliques a la detection de phenols, galactosides et de l glutamate via l'immobilisation de poly phenol oxydase, galactose oxydase et de glutamate oxydase. Les performances analytiques des biocapteurs amperometriques ont ete modulees en modifiant la structure du biomateriaux. De plus, le transfert d'activite en milieu organique a ete exemplifie par la detection de phenol dans chc13. Par ailleurs, la miniaturisation des bio electrodes a ete entreprise avec succes pour le biocapteur a glutamate. La synthese de nouveaux amphiphiles pyrroliques fonctionnalises par un groupe viologene a permis la realisation d'un biocapteur a nitrate, grace a la connexion electrique directe entre la nitrate reductase et le polymere. La sophistication et la modulation de la composition du biomateriau ont permis son optimisation
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ARYA-MORTEZAEI, FARIBA. "Reactivite thermique de n-alcenyliminocetenes." Reims, 1987. http://www.theses.fr/1987REIMS010.
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Les composes du titre conduisent a differentes cetones heterocycliques : desazepinones-4, des aza-3bicyclo (3. 2. 0)heptenes-2ones-7, des formyl-3 pyridinones-4. Les azobicyclohepotenones conduisent a des pyrrolidines et a des oxaziridines polycylcliques
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呂幹雄 and Kon-hung Lui. "Complementary approaches to 2,2-disubstituted 1,4-diketones, and the preparation and properties of 3H- and 3H-pyrroles derived from them." Thesis, The University of Hong Kong (Pokfulam, Hong Kong), 1988. http://hub.hku.hk/bib/B31231299.
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Fabre, Bruno. "Synthèse et étude de films de polymères conducteurs électroniques dopés par des hétéropolyanions : application à la réduction électrocatalytique de NO2- et à la détection du NO in vivo." Université Joseph Fourier (Grenoble ; 1971-2015), 1994. http://www.theses.fr/1994GRE10158.
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Ce travail est consacre a la synthese, la caracterisation physico-chimique et l'application de films de polymeres conducteurs electroniques (pce) incluant des heteropolyanions (hpa). Ces entites minerales, connues pour leurs remarquables proprietes redox, sont immobilisees en tant qu'anion dopant lors de la synthese electrochimique des pce. Dans un premier temps, nous montrons qu'une electrode modifiee par un film de poly(3-methyl thiophene) dope par un hpa de structure de keggin xm#1#2o#4#0#n#- (x = p, si ; m = w, mo et n = 3, 4) presente l'electroactivite des deux partenaires. La reponse electrochimique associee a l'hpa n'est pas modifiee apres son immobilisation, pour peu que les conditions de l'electrosynthese du film soient optimisees (rapport monomere/hpa et valeur du potentiel impose). La geometrie particuliere de l'hpa n'induit pas une structure organisee dans le poly(3-methyl thiophene). Afin de remonter a une explication structurale du materiau, nous entreprenons, dans un second temps, l'etude d'un compose modele base sur un oligomere du thiophene (6t)#4#p#+/(pmo#1#2o#4#0)#p#- (6t represente l'hexamere du thiophene et 3 < p < 4). Malheureusement, la tres faible solubilite de ce sel ne permet pas des cristallisations adequates pour des etudes cristallographiques. Les films de pce/hpa peuvent realiser des electrocatalyses, a condition de choisir la bonne association. Dans ce sens, nous mettons en evidence qu'une electrode modifiee par un film de poly(n-methyl pyrrole) incluant un hpa mixte fepw#1#1o#3#9(h#2o)#4#- presente une remarquable stabilite electrochimique et activite electrocatalytique vis-a-vis de la reduction de no#2#-. Le mecanisme de reduction en phase immobilisee passe par un complexe fer-nitrosyl fepw#1#1o#3#9(no)#5#- qui assure la selectivite de cette catalyse chimique electroassistee. Cette electrode modifiee permet de la meme maniere la reduction catalytique du no dissous dans l'eau. Cette molecule, actuellement reconnue comme mediateur intercellulaire essentiel, peut etre detectee in vivo a partir d'une fibre de carbone modifiee par le depot catalytique precedent. Cette etude, realisee en collaboration avec r. Cespuglio (inserm, lyon) constitue un des rares exemples de detection fonctionnelle et en temps reel de cette molecule
Book chapters on the topic "Pyrrole derive"
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Talapatra, Sunil Kumar, and Bani Talapatra. "Camptothecin, A Novel Pyrrolo[3,4-b]quinoline Alkaloid: Derived by Modification of an Indole System." In Chemistry of Plant Natural Products, 909–13. Berlin, Heidelberg: Springer Berlin Heidelberg, 2014. http://dx.doi.org/10.1007/978-3-642-45410-3_29.
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Taber, Douglass F. "Heteroaromatic Construction: The Jia Synthesis of (-)- cis -Clavicipitic Acid." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0065.
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Simultaneously, Aaran Aponick of the University of Florida (Organic Lett. 2009, 11, 4624) and Shuji Akai of the University of Shizuoka (Organic Lett. 2009, 11, 5002) reported the Au-mediate conversion of a propargylic diol such as 1 to the furan 2. Pyrroles can also be prepared using the same protocol. Jason K. Sello of Brown University developed (Organic Lett. 2009, 11, 2984) the direct aldol condensation of an acetoacetate 3 with the protected 1,3-dihydroxy acetone 4 to give 5, the methyl ester of a methylenomycin furan (MMF) bacterial-signaling molecule from Streptomyces coelicolor. Nobuharu Iwasawa of the Tokyo Institute of Technology demonstrated (Angew. Chem. Int. Ed. 2009, 48, 8318) that the imine 6 was sufficiently nucleophilic to react with the Rh vinylidene derived from the alkyne 7, leading to the pyrrole 8. Min Shi of the Shanghai Institute of Organic Chemistry extended (J. Org. Chem. 2009, 74, 5983) the reactivity of methylene cyclopropanes to the condensation of the aldehyde 9 with an acyl hydrazide, to give the pyrrole 11. Xue-Long Hou, also of the Shanghai Institute of Organic Chemistry, described (Tetrahedron Lett. 2009, 50, 6944) the Au-mediated reorganization of the alkynyl aziridine 12 to the pyrrole 13. Masahiro Yoshida of the University of Tokushima carried out (Tetrahedron Lett. 2009, 50, 6268) a similar rearrangement under oxidative conditions, giving the iodinated pyrrole 15. André M. Beauchemin of the University of Ottawa showed (Angew. Chem. Int. Ed. 2009, 48, 8325) that under acid catalysis, the oxime 16 cyclized to the pyridine 17. Shunsuke Chiba of Nanyang Technological University developed (J. Am. Chem. Soc. 2009, 131, 12570) the Mn(III)-mediated fusion of a cyclopropanol 18 with an alkenyl azide 19 to deliver the pyridine 20. Kazuaki Shimada of Iwate University found (Tetrahedron Lett. 2009, 50, 6651) that an isotellurazole such as 21, easily prepared from the corresponding alkyne, condensed with another alkyne 22, delivering the pyridine 23 with high regiocontrol. Christopher J. Moody of the University of Nottingham devised (Organic Lett. 2009, 11, 3686) a new route to the 1,2,4-triazine 24 from an α-diazoacetoacetate. He carried 24 on to the pyridine 26 by condensation with norbornadiene 25.
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Singh, Keisham S., and Mahesh S. Majik. "Pyrrole-Derived Alkaloids of Marine Sponges and Their Biological Properties." In Studies in Natural Products Chemistry, 377–409. Elsevier, 2019. http://dx.doi.org/10.1016/b978-0-444-64185-4.00010-1.
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Hopkins, Paul B. "DNA sequence selectivity of the pyrrole-derived, bifunctional alkylating agents." In Advances in DNA Sequence-Specific Agents, 217–39. Elsevier, 1996. http://dx.doi.org/10.1016/s1067-568x(96)80011-9.
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Taber, Douglass F. "The Harran Synthesis of (+)-Roseophilin." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0107.
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Ansa-bridged prodiginines include (+)-roseophilin B 3 and streptorubin B. The observation that streptorubin B potentiated apoptopic signaling in cell culture led to the development of obatoclax, currently being evaluated for the treatment of leukemia. Patrick G. Harran of UCLA devised (J. Am. Chem. Soc. 2013, 135, 3788) what promises to be a general route to the prodiginines, a key step of which was the cyclization of 1 to 2. In planning the synthesis of 1, the authors took advantage of the relative inertness of a monosubstituted alkene. Friedel-Crafts acylation of 5 proceeded smoothly without affecting the distal double bond. Reduction then completed the preparation of 7. The preparation of 1 continued from the pyrrole 9, prepared from the pyridine 8. Addition of the derived enoate to the aldehyde 10 proceeded smoothly, to give, after oxidation and acid-mediated rearrangement, the furan 12. Selective metalation followed by carboxylation gave the acid 13, which was combined with 7 to give 15. Deprotonation of 15 gave an intermediate that reacted primarily on the pyrrole N. This intermediate was then reacted with diethylchlorophosphite to give, after oxidation, the phosphoramide 16. Advantage was then taken of the organometallic reactivity of the monosubstituted alkene of 16, as Ru-mediated cross metathesis with 17 followed by reduction completed the preparation of 1. The diheteroaryl ketone of 1 is not enolizable. On exposure to KHMDS, the dialkyl ketone will be deprotonated reversibly. Either enolate could add to the diheteroaryl ketone, but only the adduct from deprotonation of the methylene could go on to alkene formation. This net dehydration may likely be driven by phosphoryl transfer to the intermediate alkoxide. The enone 2 is prochiral. Hydrogenation with an enantiopure catalyst proceeded with high de and 67% ee. Remediated intramolecular Friedel-Crafts addition of the dialkyl ketone to the pyrrole followed by acid-mediated rearrangement then delivered (+)-roseophilin 3. There are several points along this synthesis at which diversity could be introduced. This should enable detailed structure–activity studies of the prodiginines.
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Taber, Douglass F. "Heteroaromatic Synthesis: The Tokuyama Synthesis of (−)-Rhazinilam." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0066.
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Mei-Huey Lin of the National Changhua University of Education rearranged (J. Org. Chem. 2014, 79, 2751) the initial allene derived from 1 to the γ-chloroenone. Displacement with acetate followed by hydrolysis led to the furan 2. A. Stephen K. Hashmi of Ruprecht-Karls-Universität Heidelberg showed (Angew. Chem. Int. Ed. 2014, 53, 3715) that the Au-catalyzed conversion of the bis alkyne 3, mediated by 4, proceeded selectively to give 5. Tehshik P. Yoon of the University of Wisconsin used (Angew. Chem. Int. Ed. 2014, 53, 793) visible light with a Ru catalyst to rearrange the azide 6 to the pyrrole 7. Cheol-Min Park, now at UNIST, found (Chem. Sci. 2014, 5, 2347) that a Ni catalyst reorganized the methoxime 8 to the pyrrole 9. A Rh catalyst converted 8 to the corresponding pyridine (not illustrated). In the course of a synthesis of opioid ligands, Kenner C. Rice of the National Institute on Drug Abuse optimized (J. Org. Chem. 2014, 79, 5007) the preparation of the pyridine 11 from the alcohol 10. Vincent Tognetti and Cyrille Sabot of the University of Rouen heated (J. Org. Chem. 2014, 79, 1303) 12 and 13 under microwave irradiation to give the 3-hydroxy pyridine 14. Tomislav Rovis of Colorado State University prepared (J. Am. Chem. Soc. 2014, 136, 2735) the pyridine 17 by the Rh-catalyzed combination of 15 with 16. Fabien Gagosz of the Ecole Polytechnique rearranged (Angew. Chem. Int. Ed. 2014, 53, 4959) the azirine 18, readily available from the oxime of the β-keto ester, to the pyridine 19. Matthias Beller of the Universität Rostock used (Chem. Eur. J. 2014, 20, 1818) a Zn catalyst to mediate the opening of the epoxide 21 with the aniline 20. A Rh catalyst effected the oxidation and cyclization of the product amino alcohol to the indole 22. Sreenivas Katukojvala of the Indian Institute of Science Education & Research showed (Angew. Chem. Int. Ed. 2014, 53, 4076) that the diazo ketone 23 could be used to anneal a benzene ring onto the pyrrole 24, leading to the 2,7-disubstituted indole 25.
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Taber, Douglass F. "Heteroaromatics: The Zhou/Li Synthesis of Goniomitine." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0067.
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Xin-Yan Wu of East China University of Science and Technology and Jun Yang of the Shanghai Institute of Organic Chemistry added (Tetrahedron Lett. 2014, 55, 4071) the Grignard reagent 1 to propargyl alcohol 2 to give an intermediate that could be borylated, then coupled under Pd catalysis with an anhydride, leading to the furan 3. Fuwei Li of the Lanzhou Institute of Chemical Physics constructed (Org. Lett. 2014, 16, 5992) the furan 6 by oxidizing the keto ester 4 in the presence of the enamide 5. Yuanhong Liu of the Shanghai Institute of Organic Chemistry prepared (Angew. Chem. Int. Ed. 2014, 53, 11596) the pyrrole 9 by reducing the azadiene 7 with the Negishi reagent, then adding the nitrile 8. Yefeng Tang of Tsinghua University found (Tetrahedron Lett. 2014, 55, 6455) that the Rh carbene derived from 11 could be added to an enol silyl ether 10 to give the pyrrole 12. Pazhamalai Anbarasan of the Indian Institute of Technology Madras reported (J. Org. Chem. 2014, 79, 8428) related results. Zheng Huang of the Shanghai Institute of Organic Chemistry established (Angew. Chem. Int. Ed. 2014, 53, 1390) a connection between substituted piperidines and pyridines by dehydrogenating 13 to 15, with 14 as the acceptor. Joseph P. A. Harrity of the University of Sheffield conceived (Chem. Eur. J. 2014, 20, 12889) the cascade assembly of the pyridine 18 by cycloaddition of 16 with 17 followed by Pd-catalyzed coupling. Teck-Peng Loh of Nanyang Technological University converted (Org. Lett. 2014, 16, 3432) the keto ester 19 into the azirine, then eliminated it to form an azatriene that cyclized to the pyridine 20. En route to a cholesteryl ester transfer protein inhibitor, Zhengxu S. Han of Boehringer Ingelheim combined (Org. Lett. 2014, 16, 4142) 21 with 22 to give an intermediate that could be oxidized to 23. Magnus Rueping of RWTH Aachen used (Angew. Chem. Int. Ed. 2014, 53, 13264) an Ir photoredox catalyst in conjunction with a Pd catalyst to cyclize the enamine 24 to the indole 25. Yingming Yao and Yingsheng Zhao of Soochow University effected (Angew. Chem. Int. Ed. 2014, 53, 9884) oxidative cyclization of 26 to 27.
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Taber, Douglass F. "Alkaloid Synthesis: Indolizidine 223AB (Cha), Lepadiformine (Kim), Kainic Acid (Fukuyama), Gephyrotoxin (Smith), Premarineosin A (Reynolds)." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0059.
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Jin Kun Cha of Wayne State University prepared (Org. Lett. 2014, 16, 6208) the allene 1 by SN2′ coupling of a cyclopropanol with a propargylic tosylate. Silver-mediated cyclization converted 1 into 2, that was reduced with diimide to the Dendrobates alkaloid indolizidine 223AB 3. Sanghee Kim of Seoul National University observed (Chem. Eur. J. 2014, 20, 17433) high diastereoselectivity in the Ireland–Claisen rearrangement of 4 to 5. The acid 5 was the key intermediate for the synthesis of the tunicate alkaloid lepadiformine 6. Tohru Fukuyama of Nagoya University also used (Eur. J. Org. Chem. 2014, 4823) an ester enolate Claisen rearrangement to set the relative and absolute configuration of 7. Pd-catalyzed cyclization then led to 8, that was carried on to the excitatory amino acid receptor agonist kainic acid 9. Gephyrotoxin 12 was so named because it incorporates structural elements from two different classes of the Dendrobates alkaloids. Martin D. Smith of the University of Oxford envisioned (Angew. Chem. Int. Ed. 2014, 53, 13826) the cascade cyclization of deprotected 10 to give, after reduction, the ketone 11. Zhen Yang of the Peking University Shenzhen Graduate School showed (Chem. Eur. J. 2014, 20, 12881) that the Rh carbene derived from 13 readily cyclized to an imine. The facial selectivity of the addition of the Grignard reagent 14 to that imine depended on the temperature of the reaction. At room temperature, 15 was formed. At low temperature, the other diastereomer predominated. Ring-closing metathesis was used for the elaboration of 15 to the Stemona alkaloid tuberostemospiroline 16. Kevin A. Reynolds of Portland State University prepared (J. Org. Chem. 2014, 79, 11674) 19 by condensation of the pyrrole 17 with the aldehyde 18. The biosynthetic enzyme, that they had overexpressed, oxidized 19 to the antimalarial alkaloid permarineosin A 20.
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Taber, Douglass F. "C–N Ring Construction: The Glorius Synthesis of ent-Monomorine." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0054.
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Ryan Gilmour of the Westfälische Wilhelms-Universität Münster employed (Chem. Eur. J. 2014, 20, 794) an organocatalyst to direct the enantioselective aziridination of 1 to 2. Vanessa Kar-Yan Lo and Chi-Ming Che of Hong Kong University devised (Angew. Chem. Int. Ed. 2014, 53, 2982) a Ru catalyst for the enantioselective aziridination (not illustrated) of terminal alkenes. Shu-Li You of the Shanghai Institute of Organic Chemistry and Aiwen Lei of Wuhan University described (Angew. Chem. Int. Ed. 2014, 53, 2443) the Pd-mediated carbonylation of 3 to the β-lactam 4. Professor You reported (J. Am. Chem. Soc. 2014, 136, 6590) the enantioselective allylation of a pyrrole 5 with 6 to give the imine 7. Maria-Paz Cabal and Carlos Valdés of the University of Oviedo showed (Eur. J. Org. Chem. 2014, 1672) that the cyclization of 8 to 9 proceeded with predictable high diastereocontrol. In one pot, Darren J. Dixon of the University of Oxford combined (ACS Catal. 2014, 4, 634) 10 and 11 to give 12 in high ee. The addition of 13 to 14 to give 15 described (Nature Chem. 2014, 6, 47) by Takashi Ooi of Nagoya University set two adjacent quaternary centers with control of both relative and absolute configuration. Scott E. Denmark of the University of Illinois devised (J. Am. Chem. Soc. 2014, 136, 8915) a catalyst for the enantioselective electrophilic cyclization of 16 to 17 with control of sidechain stereochemistry. Using commercial acetone cyanohydrin 19, Christian V. Stevens of Ghent University cyclized (Eur. J. Org. Chem. 2014, 1296) 18 to the nitrile 20. George W. J. Fleet, also of the University of Oxford, used (Eur. J. Org. Chem. 2014, 2053) similar conditions to convert the sugar-derived acetonide 21 into 22. Michael B. Tropak of the University of Toronto and Dilip P. Dhavale of the University of Pune showed (J. Org. Chem. 2014, 79, 4398) that the nitrone derived from 21 added to an alkene 23 with high facial selectivity, leading to the piperidine 24. In the course of a synthesis of syringolin A, Satoshi Ichikawa of Hokkaido University effected (Angew. Chem. Int. Ed. 2014, 53, 4836) intramolecular Ugi three-component coupling of the isonitrile 25, the acid 26, and the amine 27, leading to the macrolactam 28.
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Taber, Douglass. "Stereoselective C-N Ring Construction." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0054.
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Ryoichi Kuwano of Kyushu University showed (J. Am. Chem. Soc. 2008, 130, 808) that diastereomerically and enantiomerically pure pyrollidines such as 2 could be prepared by hydrogenation of the corresponding pyrrole. Victor S. Martín of Universidad de la Laguna found (Organic Lett. 2008, 10, 2349) that the stereochemical outcome of the pyrrolidine-forming Nicholas cyclization could be directed by the protecting group on the N. Jianbo Wang of Peking University established (J. Org. Chem. 2008, 73, 1971) a convenient route to diazo esters such as 6. N-H insertion led to the pyrrolidine, which Zhen-Jiang Xu of the Shanghai Institute of Organic Chemistry and Chi-Ming Che of the University of Hong Kong showed (Organic Lett. 2008, 10, 1529) could be reduced with high diastereoselectivity to the hydroxy ester 7. Alternatively, Professor Wang found that photochemical Wolff rearrangement of 6 delivered the pyrrolidone 8 . Martin J. Slater and Shiping Xie of GlaxoSmithKline optimized (J. Org. Chem. 2008, 73, 3094) the hydroquinine catalyzed enantioselective 3+2 cycloaddition of 9 and 10, leading to the pyrrolidine 11 with high diastereocontrol. Shu Kobayashi of the University of Tokyo developed (Adv. Synth. Cat. 2008, 350, 647) a practical protocol for the aza Diels-Alder construction of enantiomerically-pure piperidines such as 14 . Biao Yu of the Shanghai Institute of Organic Chemistry cyclized (Tetrahedron Lett. 2008, 49, 672) the product from the proline-catalyzed enantioselective aldol of 15 and 16, leading to the substituted piperidine 17 . Michael Shipman of the University of Warwick described (Tetrahedron Lett. 2008, 49, 250) the cyclization of the aziridine derived from 18, that proceeded to give 19 as a single diastereomer, apparently via kinetic side-chain protonation. Takeo Kawabata of Kyoto University found (J. Am. Chem. Soc. 2008, 130, 4153) that intramolecular alkylation to form four, five and six-membered rings from amino esters such as 21 proceeded with remarkable enantioretention. Géraldine Masson and Jieping Zhu of CNRS, Gif-sur-Yvette, condensed (Organic Lett. 2008, 10, 1509) cinnamaldehyde 23 with cyanide and an ω-alkenyl amine to give the intramolecular aza-Diels-Alder substrate 24. Hongbin Zhai of the Shanghai Institute of Organic Chemistry acylated (J. Org. Chem. 2008, 73, 3589) 26 with 27, leading to the ring-closing metathesis precursor 28.
Conference papers on the topic "Pyrrole derive"
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Goti, Andrea, Valentina Fedi, and Alberto Brandi. "A Straightforward Route to Enantiopure Pyrrolizidines by Cycloaddition to Pyrroline N-Oxides Derived from the Chiral Pool." In The 1st International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 1997. http://dx.doi.org/10.3390/ecsoc-1-02011.
Full textReports on the topic "Pyrrole derive"
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Shu, Ching-Fong, and Mark S. Wrighton. Synthesis and Charge Transport Properties of Polymers Derived from Oxidation of 1-H-1'(6-pyrrol-1-yl)-hexyl-4,4'-bipyridinium. Fort Belvoir, VA: Defense Technical Information Center, August 1988. http://dx.doi.org/10.21236/ada198070.
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