Relevant bibliographies by topics / Indolizine

Academic literature on the topic 'Indolizine'

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Published: 4 June 2021
Last updated: 4 May 2024

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Journal articles on the topic "Indolizine"

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Albota, Florin, Mino R. Caira, Constantin Draghici, Florea Dumitrascu, and Denisa E. Dumitrescu. "Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin indolizine synthesis." Beilstein Journal of Organic Chemistry 12 (November 23, 2016): 2503–10. http://dx.doi.org/10.3762/bjoc.12.245.

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The synthesis of sydnones heteroarylated at C-4 with an indolizine was achieved by Chichibabin (Tschitschibabin) indolizine synthesis starting from the corresponding sydnone-N-pyridinium bromides. The latter compounds were also transformed to sydnone-indolizines connected through a keto group at the C-4 position by refluxing them in 1,2-epoxybutane with an activated alkyne. The structures of the new compounds were assigned by FTIR, NMR spectroscopy and X-ray analysis.
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Guidotti, Bruno Boni, Thiago Sabino da Silva, José Tiago Menezes Correia, and Fernando Coelho. "Brønsted-acid-catalyzed selective Friedel–Crafts monoalkylation of isatins with indolizines in water." Organic & Biomolecular Chemistry 18, no. 37 (2020): 7330–35. http://dx.doi.org/10.1039/d0ob01714k.

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Chan, Siu-Chung, Chi-Fung Yeung, Hau-Lam Shek, Sze-Wing Ng, Sheung-Ying Tse, Man-Kit Tse, Shek-Man Yiu, and Chun-Yuen Wong. "Iron(ii)-induced cycloisomerization of alkynes via “non-vinylidene” pathways for iron(ii)-indolizine and -indolizinone complexes." Chemical Communications 56, no. 83 (2020): 12644–47. http://dx.doi.org/10.1039/d0cc05081d.

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Botezatu (Dediu), Andreea Veronica, Georgiana Horincar, Ioana Otilia Ghinea, Bianca Furdui, Gabriela-Elena Bahrim, Vasilica Barbu, Fanica Balanescu, Lidia Favier, and Rodica-Mihaela Dinica. "Whole-Cells of Yarrowia lipolytica Applied in “One Pot” Indolizine Biosynthesis." Catalysts 10, no. 6 (June 5, 2020): 629. http://dx.doi.org/10.3390/catal10060629.

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A series of yeast strains was tested in order to evaluate their catalytic potential in biocatalysis of one-pot indolizine’s synthesis. Yeast cultivation was performed in a submerged system at 28 °C for 72 h at 180 rpm. An assessment of the reagents’ toxicity on yeast viability and metabolic functionality concluded that the growth potential of three Yarrowia lipolytica strains were least affected by the reactants compared to the other yeast strains. Further, crude fermentation products (biomass and cell-free supernatant)—obtained by submerged cultivation of these yeasts—were used in multistep cascade reactions for the production of fluorescent indolizine compounds with important biologic activities. A whole–cell catalyzed multicomponent reaction of activated alkynes, α-bromo-carbonyl reagents and 4,4′-bipyridine, at room temperature in buffer solution led to the efficient synthesis of bis-indolizines 4a, 4b and 4c, in good-to-excellent yields (47%–77%). The metabolites of the selected Y. lipolytica strains can be considered effective biocatalysts in cycloaddition reactions and the high purity and bioconversion yields of the synthesized indolizines indicates a great potential of this type of “green” catalysts. Seeds of Triticum estivum L. were used to investigate the impact of the final products on the germination and seedling growth. The most sensitive physiological parameters suggest that indolizines, at the concentrations tested, have non-toxic effect on germination and seedling growth of wheat, fact also confirmed by confocal laser scanning microscopy images.
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Venugopala, Katharigatta N., Sandeep Chandrashekharappa, Subhrajyoti Bhandary, Deepak Chopra, Mohammed A. Khedr, Bandar E. Aldhubiab, Mahesh Attimarad, and Bharti Odhav. "Efficient Synthesis and Characterization of Novel Substituted 3-Benzoylindolizine Analogues via the Cyclization of Aromatic Cycloimmoniumylides with Electrondeficient Alkenes." Current Organic Synthesis 15, no. 3 (April 27, 2018): 388–95. http://dx.doi.org/10.2174/1570179414666171024155051.

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Background: Indolizine pharmacophore is known to exhibit various promising pharmacological properties such as analgesic, anticancer, antihistaminic, antidiabetic, anti-inflammatory, antileishmanic, antimicrobial, antimutagenic, antioxidant, antitubercular, antiviral, larvicidal and herbicidal activities. Objective: In the present investigation, it was envisaged to synthesize a series of novel ethyl-7-substituted-3-(4- substituted benzoyl)-2-substituted indolizine-1-carboxylates by employing chromium(IV)oxide as dehydrogenating agent with triethylamine combination. Method: Synthesis of a series of proposed polysubstituted indolizines by employing chromium(IV)oxide as dehydrogenating agent with triethylamine combination. Final compounds were characterized by spectroscopic techniques viz fourier-transform infrared spectroscopy, nuclear magnetic resonance spectroscopy, liquid chromatography- mass spectrometry, elemental analysis and selected title compound diethyl-3-(4- cyanobenzoyl)indolizine-1,2-dicarboxylate by single crystal X-ray method. Results: Aromatic cycloimmoniumylides undergo smooth cyclization with electron-deficient alkenes in the presence of triethylamine and DMF at room temperature to afford intermediates ethyl 7-substituted-2- substituted-3-(4-substituted benzoyl)-1,2,3,8a-tetrahydroindolizine-1-carboxylates, which on dehydrogenation with chromium(IV)oxide to obtain the title compounds ethyl-7-substituted-3-(4-substituted benzoyl)-2- substituted indolizine-1-carboxylates. Conclusion: The research was focused on developing an efficient protocol for the synthesis of a novel series of ethyl 3-substituted benzoyl-7-substituted-2-substituted indolizine-1-carboxylates with suitable pharmacological properties in good to excellent yields.
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Ma, Lanchao, Bing Chen, Yunlong Guo, Yongri Liang, Dongmei Zeng, Xiaowei Zhan, Yunqi Liu, and Xingguo Chen. "NIR polymers and phototransistors." Journal of Materials Chemistry C 6, no. 47 (2018): 13049–58. http://dx.doi.org/10.1039/c8tc03917h.

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A novel bisthiophene-fused diketopyrrolopyrrole unit (4,11-bis(2-octyldodecyl)-7H,14H-thieno[3′,2′:7,8]indolizino[2,1-a]thieno[3,2-g]indolizine-7,14-dione, BTI) has been designed as an electron acceptor and used to copolymerize with thiophene and bithiophene as electron donors to construct two D–A conjugated polymers, P1 and P2via Stille coupling, respectively.
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Chudík, Miloslav, Štefan Marchalín, and Katarína Havrilová. "Synthesis and Spectral Properties of Methyl 6-Acetyl- or 6-Cyano-3-amino-2-benzoyl-7-furyl-5-methylindolizine-8-carboxylates." Collection of Czechoslovak Chemical Communications 63, no. 6 (1998): 826–34. http://dx.doi.org/10.1135/cccc19980826.

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Good yields of methyl 6-acetyl- or 6-cyano-3-amino-2-benzoyl-5-methyl-7-(5-substituted-2-furyl)indolizine-8-carboxylates (5a-5f) were obtained in the reaction of corresponding 5-acetyl- or 5-cyano-2-formyl-4-(5-substituted-2-furyl)-6-methyl-1,4-dihydropyridine-3-carboxylated (4a-4f) with 3-phenyl-3-oxopropanenitrile. Spectral properties of the indolizines 5 are discussed.
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Venugopala, Katharigatta N., Christophe Tratrat, Melendhran Pillay, Fawzi M. Mahomoodally, Subhrajyoti Bhandary, Deepak Chopra, Mohamed A. Morsy, et al. "Anti-Tubercular Activity of Substituted 7-Methyl and 7-Formylindolizines and In Silico Study for Prospective Molecular Target Identification." Antibiotics 8, no. 4 (December 3, 2019): 247. http://dx.doi.org/10.3390/antibiotics8040247.

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Novel series of diversely substituted indolizines were designed, synthesized, and evaluated for their in vitro anti-mycobacterial activity against H37Rv and multi-drug-resistant (MDR) strains of Mycobacterium tuberculosis (MTB). Many compounds exhibited significant inhibitory activity against MTB H37Rv strains. Indolizines 2d, 2e, and 4 were also found to be active against MTB clinical isolates with multi-resistance to rifampicin and isoniazid. Indolizine 4 was identified as the most promising anti-mycobacterial agent, displaying minimum inhibitory concentration (MIC) values of 4 and 32 μg/mL against H37Rv and MDR strains, respectively. Furthermore, an in silico study was carried out for prospective molecular target identification and revealed favorable interactions with the target enzymes CYP 121, malate synthase, and DNA GyrB ATPase. None of the potent molecules presented toxicity against peripheral blood mononuclear (PBM) cell lines, demonstrating their potentiality to be used for drug-sensitive and drug-resistant tuberculosis therapy.
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Matsumoto, Kiyoshi, Yukio Ikemi, Motoo Shiro, Takane Uchida, and James William Lown. "Reactions of 5-cyano-1,4-diphenylpyridazino[4,5-a]indolizines with dimethyl acetylenedicarboxylate: regioselective formation of 1:2 Michael type adducts." Canadian Journal of Chemistry 71, no. 4 (April 1, 1993): 529–33. http://dx.doi.org/10.1139/v93-075.

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Reactions of 5-cyano-1,4-diphenylpyridazino[4,5-a]indolizines with dimethyl acetylenedicarboxylate afforded the 1:2 adducts regioselectively and, unexpectedly, in a Michael fashion rather than in a 1,3-dipolar manner. The structure of the products was established by X-ray crystallography. Regiospecific formation of the observed product 3 can be explained by the higher nucleophilicity of the nitrogen at the 2 position than at the 3 position of the 5-cyano-1,4-diphenylpyridazino[4,5-a]indolizine 1 owing to the contribution of a resonance structure 5 to the hybrid. This favors two successive Michael additions to two equivalents of dimethyl acetylenedicarboxylate affording the observed 1:2 adducts 3.
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Kim, Sunmi, Jeong Hwa Lee, Seok Hyun Yoon, and Ikyon Kim. "A regioselective [4 + 2] annulation approach to 5-acylindolizine-7-carbonitriles: generation of poly-substituted pyridines." Organic & Biomolecular Chemistry 19, no. 26 (2021): 5806–17. http://dx.doi.org/10.1039/d1ob00788b.

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A highly efficient [4 + 2] annulation approach to poly-functionalized indolizine-7-carbonitriles enables us to install nitrile, (hetero)aryl/alkyl, and acyl groups regioselectively on the pyridine unit of indolizine.
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Dissertations / Theses on the topic "Indolizine"

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Bode, Moira Leanne. "Synthetic and spectroscopic studies of indolizine derivatives." Thesis, Rhodes University, 1994. http://hdl.handle.net/10962/d1005050.

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The crystalline compound resulting from thermal cyclization of the Baylis-Hillman product, methyl 3-hydroxy-2-methylene-3-(2-pyridyl)propanoate, has been identified as the indolizine derivative, methyl indolizine-2-carboxylate, and this approach involving the reaction of pyridine-2-carboxaldehydes and acrylate analogues has been established as a general route to 2-substituted indolizines. The ease of cyclization the Baylis-Hillman products to indolizines has been shown to increase by converting the hydroxy group to an acetoxy group, and a range of acetylated Baylis-Hillman products were prepared and cyc1ized to the corresponding 2-substituted indolizines, generally in good overall yield. In the reaction of pyridine-2-carboxaldehyde and methyl vinyl ketone, the intermediate cyclized readily and directly to the corresponding indolizine. One- and two-dimensional ¹H and ¹³C NMR analysis of the 2-substituted indolizine products has permitted complete assignment of all ¹H and ¹³C NMR signals, as well as the measurement of all coupling constants for these compounds. A kinetic and mechanistic study has been conducted on the Baylis-Hillman reaction using ¹H NMR spectroscopy. A range of substrates has been examined and the reaction has been found to be third-order overall. A mechanism involving an addition - elimination sequence is proposed, which fits the kinetic data and accounts for observed substituent effects. Reaction of N,N-dimethylacrylamide with pyridine-2-carboxaldehyde in the presence of the tertiary amine catalyst, DABCO, in chloroform, yielded an unexpected product which has been identified by single crystal X-ray diffraction analysis as 1-(2,2,2-trichloro-1-hydroxyethyl)pyridine. Attempted extension of the general indolizine route to the preparation of chromene systems by reacting salicylaldehyde with methyl acrylate in the presence of DABCO, also led to an unexpected, crystalline material, identified by single crystal X-ray diffraction analysis as the coumarin derivative, 3-[(2-formylphenoxy)methyl]coumarin.A series of chloroquine analogues have been prepared from indolizine-2-carboxylic acid, pyrrolo[I,2-a]quinoline-2-carboxylic acid and imidazo[I,2-a]pyridine-2-carboxylic acid by reaction with suitable amines in the presence of the coupling reagent 1, I' -carbonyldiimidazole. This route has been shown to be a vast improvement on earlier procedures and has provided access to both secondary and tertiary indolizine-2-carboxamides. A range of N,N-dialkylindolizine-2-carboxamides have been prepared by this route, and the influence of substituents on their N-CO rotational energy barriers has been determined using variable temperature ¹H and ¹³C NMR techniques. Intercalation with natural DNA by both chloroquine and the synthesized chloroquine analogues has been examined using UV spectrophotometry, and ¹H and ³¹P NMR spectroscopy. The pyrrolo[I,2-a]quinolines have been shown to be DNA intercalators with binding affinities similar to that of the known antimalarial intercalator, chloroquine. In a preliminary study the synthesis of a short oligonucleotide has been undertaken and changes have been observed in the ¹H and ³¹P NMR spectra of the oligonucleotide on addition of the intercalator, chloroquine.
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Sevrain, Nicolas. "Synthèse de nouveaux systèmes phosphorés à chiralité axiale et leurs applications." Thesis, Montpellier, Ecole nationale supérieure de chimie, 2017. http://www.theses.fr/2017ENCM0019.

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La demande croissante de molécules énantiopures pour la chimie pharmaceutique et agrochimique est l'un des enjeux majeurs actuels de l'industrie chimique. De plus, les nouvelles réglementations environnementales récentes forcent l'émergence de procédés efficaces, rentables et respectueux de l'environnement pour la fabrication de ces nouvelles entités chimiques. Les méthodes impliquant l'utilisation de catalyseurs présentent des avantages évidents par rapport à des méthodes stœchiométriques. À ce titre, les ligands phosphorés ont joué un rôle clé dans l'évolution de la catalyse asymétrique. Leur activité catalytique est une balance entre leurs propriétés électroniques et stériques et il n’existe pas à l’heure actuelle d’inducteur chiral universel. De plus, leur modification est loin d’être triviale au regard des procédures complexes nécessaires pour en modifier la structure.Ces travaux de thèse s’inscrivent dans le développement de nouveaux systèmes phosphorés à chiralité axiale, dont le BINAP en est l’exemple le plus représentatif. Notre premier objectif a été la synthèse et l’étude de systèmes bihétéroaromatiques à 5 chaînons basés sur le motif bis-indolizine, dont le motif hétérocyclique est connu pour la richesse électronique de son noyau aromatique à 10 électrons π. Le second objectif est l’utilisation d’oxydes de bis-triazolylphosphines pour des réactions énantiosélectives d’Abramov, d’allylation d’aldéhydes et pour finir d’aldolisation réductrice
The growing demand of enantiopure molecules for applications in life sciences (pharmaceutical and agrochemical chemistry) or in new fragrances is one of the major issue of the late decades in chemical industry. Moreover, recent environmental regulations pushed the emergence of efficient, cost-effective and environmental-friendly processes for the manufacture of these new chemical entities. The methods involving the use of catalysis have clear advantages over those requiring stoichiometric amounts of reagents and phosphine ligands has played a key role in the evolution of catalysis. However fine tuning of the catalytic activity by modification of the electronic/steric properties of the ligand systems is far from trivial mainly because of the difficulty and cumbersome procedures for structural modification of the ligand scaffolds.This work was focused on the development of new axial chiral phosphorus structures, of which BINAP is the most representative example. The first objective was the synthesis of 5-membered biheteroaromatic systems based on the bis-indolizine scaffold, whose the heterocyclic system is known for the electronic richness of the 10-π electron aromatic core. The second objective was the application of bis-triazolylphosphine oxides in enantioselective Abramov, allylation of aldehydes and finally reductive aldolisation reactions
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Stegarescu-Furdui, Bianca. "Synthèse en série bipyridine. Etude de l'interaction avec l'ADN." Phd thesis, Université Joseph Fourier (Grenoble), 2006. http://tel.archives-ouvertes.fr/tel-00166634.

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Nous avons développé la synthèse d'hétérocycles indoliziniques fonctionnalisés par un cation pyridinium et étudié leur interaction avec L'ADN. L'étape-clé pour accéder aux indolizines est la cycloaddition [3+2]-dipolaire des ylures dérivés des sels quaternaires de la 4,4'-bipyridine avec des dipolarophiles. La synthèse a été effectuée par la voie classique (chauffage en solvant) et par irradiation avec des micro-ondes (“chimie verte”). Nous avons étudié les propriétés acido-basiques des sels diquaternaires et leur activité biologique sur une série de microorganismes. Par ailleurs les propriétés électriques et optiques ainsi que la photoluminescence des indolizines se sont révélées prometteuses pour des applications comme les traceurs biomédicaux. L'interaction des indolizines avec l'ADN a aussi été étudiée. Finalement, nous avons évalué les propriétés antioxydantes des indolizines, qui ont montré une activité inhibitrice de la peroxydation des huiles végétales in vitro.
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Martinez, Thibaut. "Cyclisation de 2-pyridylallènes : vers de nouveaux dérivés d’indolizines et ligands carbéniques chiraux." Thesis, Sorbonne université, 2019. https://accesdistant.sorbonne-universite.fr/login?url=http://theses-intra.upmc.fr/modules/resources/download/theses/2019SORUS273.pdf.

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Les travaux réalisés dans le cadre de cette thèse sont consacrés à l’étude de réactions de cyclisations de 2-pyridylallènes à l’aide de différentes espèces électrophiles. Des 2-pyridylallènes tétrasubstitués ont ainsi été synthétisés et cyclisés en conditions acides, avec différents halogènes électrophiles, des chalcogènes ainsi que de l’or (I) pour donner de nouveaux motifs indoliziniums. Des indolizines 1,3-substitués iodées en position 2 ont également été obtenues permettant une post-fonctionnalisation par couplage croisé. L’utilisation d’or (I) comme électrophile mène à de nouveaux complexes dont les ligands rassemblent les critères structuraux pour être considérés comme des NHCs. Les propriétés électroniques (σ-donation et π-acidité) de ce type de ligand ont été évaluées théoriquement et expérimentalement : si ces composantes électroniques se sont toutes deux révélées très élevées, la σ-donation semble surpasser celle des NHCs décrits dans la littérature. Certains complexes chiraux ont pu être efficacement utilisés en catalyse énantiosélective. Il apparaît clairement que la présence du groupement oxyde de phosphine est nécessaire pour obtenir une énantiosélectivité élevée dans le cas de l’hydroxyalkoxylation intramoléculaire d’un y-allénol. Ainsi, un très bon rapport énantiomérique de 91:9 et un rendement quantitatif ont été obtenus
This PhD work focused on the electrophile-induced cyclisation of 2-pyridylallenes. Various tetrasubstituted 2-pyridylallenes were synthesized and cyclized in acidic conditions, using electrophilic halogens, chalcogens and gold (I) species to afford new indoliziniums scaffolds. The synthesis of 1,3-indolizines bearing an iodine atom in position 2 was also performed, allowing a further late 2-functionnalization step by cross coupling reactions. Using gold (I) as an electrophile gave access to new gold complex bearing NHC type ligands. The electronic properties (σ-donation et π acidity) of this type of ligand were theoretically and experimentally investigated: if both of them were found especially strong, the σ-donation seems to overcome that of the NHCs described since then. Some chiral complexes have been used efficiently in enantioselective catalysis. It appeared clearly that the presence of the phosphine oxyde moiety is necessary to obtain a high enantioselectivity during the intramolecular hydroxyalkoxylation of γ-allenol. An excellent enantiomeric ratio of 91:9 and a quantitative yield were obtained
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Stegarescu-Furdui, Bianca. "Synthèse en série bipyridine. Etude de l'interaction avec l'ADN." Phd thesis, Grenoble 1, 2006. http://www.theses.fr/2006GRE10187.

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Nous avons développé la synthèse d’hétérocycles indoliziniques fonctionnalisés par un cation pyridinium et étudié leur interaction avec L’ADN. L’étape-clé pour accéder aux indolizines est la cycloaddition [3+2]-dipolaire des ylures dérivés des sels quaternaires de la 4,4’-bipyridine avec des dipolarophiles. La synthèse a été effectuée par la voie classique (chauffage en solvant) et par irradiation avec des micro-ondes (“chimie verte”). Nous avons étudié les propriétés acido-basiques des sels diquaternaires et leur activité biologique sur une série de microorganismes. Par ailleurs les propriétés électriques et optiques ainsi que la photoluminescence des indolizines se sont révélées prometteuses pour des applications comme les traceurs biomédicaux. L’interaction des indolizines avec l’ADN a aussi été étudiée. Finalement, nous avons évalué les propriétés antioxydantes des indolizines, qui ont montré une activité inhibitrice de la peroxydation des huiles végétales in vitro
We have developped the synthesis of heterocycles derived from indolizines and carrying a cationic pyridinium substituent, and studied their interaction with DNA. The key-step of the synthesis of the indolizines is a [3+2] dipolar cycloaddition of ylides formed from quaternary 4,4'-bipyridinium salts with dipolarophiles. The synthesis was done either in classical conditions (solvent, temperature) or by microwave irradiation ("green chemistry"). We have studied the acid-base properties of the bipyridinium salts and their biological activities. The electrical and optical properties along with the photolumiscence of theindolizines are promissing for potential applications as biomedical markers. The interaction of indolizines with DNA was also studied. Finally, we have evaluated the antioxidant properties of indolizines, that have shown an inhibition of peroxidation of vegetal oils in vitro
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Beck, Daniel Antony Speedie, and beckautomatic@gmail com. "Stereoselective intramolecular Michael addition reactions of pyrrole and their application to natural product syntheses." The Australian National University. Research School of Chemistry, 2006. http://thesis.anu.edu.au./public/adt-ANU20070130.130009.

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Chapter one; “(-)-Rhazinilam and (-)-Rhazinal: Alkaloids with Anti-mitotic Properties Derived from Kopsia teoi”, provides the background information behind the motives that initiated this research project. The plant alkaloid (-)-rhazinilam [(-)-1] and its naturally-occurring derivative (-)-rhazinal [(-)-13] both exhibit potent anti-mitotic activities and, as such, are interesting targets for total synthesis. Chapter one is a review of the literature regarding these two compounds and discusses the occurrence, proposed biosynthetic origins, structural elucidation and biological activites of compound (-)-1 and that of its analogues including alkaloid (-)-13. Previous total syntheses of these two compounds are then examined, concluding with the only reported total synthesis of compound (-)-13. Developed within the Banwell research group, this total synthesis produced the racemic modification of alkaloid (-)-13 due to a lack of any stereocontrol in the key intramolecular Michael addition step. This unprecedented key step, involving cyclisation of the C2 of pyrrole onto an N-tethered and ?,?-disubstituted acrylate to produce a quaternary-carbon stereogenic centre, would be of greatly enhanced utility if it could be achieved in a catalytic-enantioselective fashion. The realisation of this goal is the central aim of the research conducted within this thesis. ¶ Chapter two; “Investigating Asymmetric Induction in the Intramolecular Michael Addition of pyrrole to N-Tethered Acrylates and Related Species”, introduces the model study used to direct research towards achieving the goal of asymmetric induction in the title process. The model is a somewhat simplified version of the original process used in the total synthesis of compound (-)-13 involving cyclisation of the C2 of pyrrole onto an N-tethered and ?-monosubstituted Michael acceptor, to produce a tertiary-carbon stereogenic centre. This simplification allows the rapid synthesis of a broad range of potential substrates for use in the title process, thus enabling the investigation of various different approaches to inducing asymmetry therein. High levels of asymmetric induction are observed with the use of chiral substrates or catalysts, facilitating the synthesis of both 6- and 7-membered rings annulated to pyrrole with construction of the relevant tertiary-carbon stereogenic centre in enantio-enriched form. For the reactions producing a 6-membered ring annulated to pyrrole, unambiguous proof of the absolute sense of asymmetric induction observed in the intramolecular Michael addition event is established using a chemical correlation study involving elaboration of a key indolizine-type cyclisation product, to the plant alkaloid of known absolute stereochemistry, (-)-tashiromine [(-)-75]. For the reaction producing a 7-membered ring annulated to pyrrole, the same information is obtained via X-ray crystallographic analyses of a dibrominated derivative of a key pyrroloazepine-type cyclisation product. ¶ Chapter three “An Enantioselective Total Synthesis of the Alkaloid (-)-Rhazinal: An Anti-mitotic Agent Isolated from Kopsia teoi.”, focuses on the application of methodology developed in the previous chapter, to the original goal of inducing asymmetry in the intramolecular Michael addition reaction, involving cyclisation of the C2 of pyrrole onto an N-tethered and ?,?-disubstituted acrylate to produce a quaternary-carbon stereogenic centre. This is ultimately achieved in a catalytic-enantioselective fashion, resulting in the first such total synthesis of the anti-mitotic alkaloid (-)-rhazinal [(-)-13]. ¶ Chapter four “Extending the Reaction Manifold to the Syntheses of Related Natural Products: A Formal Total Synthesis of (+)-Aspidospermidine and Syntheses of (-)-Rhazinilam and (-)-Leuconolam from (-)-Rhazinal”, describes three extensions to the reaction manifold used in the enantioselective total synthesis of alkaloid (-)-13: The acquisition in an enantioselective manner, of an intermediate previously obtained in racemic form, en route to the racemic modification of the natural product (±)-aspidospermidine [(±)-134], constitutes a formal and enantioselective total synthesis of (+)-aspidospermidine [(+)-134]. The direct deformylation of (-)-rhazinal [(-)-13], is carried out, to produce the parent alkaloid (-)-rhazinilam [(-)-1]. The pyrrole ring present in (-)-rhazinilam [(-)-1] is oxidised, to produce the related natural product (-)-Leuconolam [(-)-12] which has not, hitherto, been prepared by total synthesis. ¶Chapter five contains the experimental procedures and characterisation data associated with compounds described in chapters two to four.
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Gizolme, Marie. "Réactions multicomposants et isonitriles." Phd thesis, Ecole Polytechnique X, 2007. http://pastel.archives-ouvertes.fr/pastel-00003258.

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Les couplages de Passerini et de Ugi, réactions multicomposants impliquant des isonitriles, ont suscité un grand intérêt ces dernières années. En effet elles permettent d'obtenir en une étape, avec de bons rendements globaux, des produits complexes et diversifiés. Tout d'abord, une nouvelle méthode de synthèse d'indolizines a été développée à partir d'un couplage entre réaction d'Ugi et cycloaddition [3+2] de sel de pyridinium. Cette étape-clé s'insère dans une cascade Sonogashira/cycloaddition/oxydation qui permet d'accéder de manière rapide à des systèmes hétérocycliques d'une grande complexité structurale, présents dans de nombreux alcaloïdes. Récemment le couplage Ugi-Smiles, équivalent du couplage de Ugi, impliquant un phénol pauvre en électrons comme composé acide, a été développé au laboratoire. Dans ce travail, nous avons étudié la possibilité d'introduire ces composés dans un couplage de Passerini. L'o-nitrophénol ainsi que des phénols hétérocycliques ont été couplés, donnant accès à une grande diversité d'aryloxyamides. Le mécanisme implique un réarrangement de Smiles final – transfert d'aryle d'un atome d'oxygène vers un autre. Nous nous sommes ensuite intéressés à l'introduction de composés soufrés dans le couplage Ugi-Smiles, permettant l'obtention en une étape de thioamides fonctionnalisés. Des produits de couplage avant réarrangement de Smiles ont pu être obtenus à différentes occasions, donnant ainsi un nouvel éclairage au mécanisme de cette réaction. En outre, des hétérocycles soufrés très divers ont été couplés avec succès donnant accès à des composés originaux.
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8

Tukulula, Matshawandile. "The design and synthesis of novel HIV-1 protease inhibitors." Thesis, Rhodes University, 2009. http://eprints.ru.ac.za/1563/.

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Delattre, François. "Nouveaux senseurs fluorescents à base de β-cyclodextrine incorporant l'unité pyridinoindolizinique : synthèse, détermination structurale et étude de l'inclusion." Littoral, 2003. http://www.theses.fr/2003DUNK0097.

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Ce travail concerne la synthèse et la caractérisation d'une série de nouveaux senseurs fluorescents, à base de β-cyclodextrine, incorporant l'unité pyridinoindolizinique. Ces dispositifs macromoléculaires ont pour caractéristiques d'induire une variation d'intensité de leurs émissions de fluorescence lors de l'inclusion de molécules invitées, à l'intérieur de leur partie macrocyclique. Dans une première partie, nous avons mis au point deux voies de synthèse dont le principe général repose sur des réactions de cycloadditions-1,3 dipolaires, à partir de sels quaternaires de 4,4'-bipyridinium et de dipolarophiles acétyléniques. Les structures des composés synthétisés ont été validées par les méthodes classiques d'analyse élémentaire et d'expériences de spectroscopies de RMN, SM, IR. Dans un second temps, nous avons étudié les phénomènes liés à l'inclusion de dérivés d'adamante et de Composés Organiques Volatils (COV), dans la cavité de la partie cyclodextrine, par spectroscopie de RMN 2D, de Dichroi͏̈sme Circulaire et de fluorescence. Cette étude met en évidence l'influence du positionnement du chromophore, de ces composés, par rapport à leur cavité hydrophobe. Les expériences de complexation ont permis la détermination de la sensitivité de ces capteurs, en solution aqueuse, vis-à-vis de leurs invités et de valider l'aspect "sensitif" de ces composés. Enfin, l'utilisation de la modélisation moléculaire, par des méthodes de Mécaniques Moléculaires et Semi-Empiriques, a contribué à mettre en évidence la structure tridimensionnelle de ces dérivés fluorescents
The present work concerns the synthesis and characterisation a series of new fluorescent molecular sensors containing β-cyclodextrin and incorporating a pyridinoindolizinic unit. These molecular devices are characterised by their ability to induce a variation of fluorescence intensity when they are incorporated a molecule in the cavity of macrocycle. In a first part, two synthesis methods where developed whose general principle is based on 1,3-cycloaddition reactions from a quaternary salts of 4,4'-bipyridinium and acetylenics dipolarophiles. Structures of the synthesized compounds were validated by the traditional methods elemental analysis and spectroscopic experiments NMR, MS, IR. In the second section, a study was made of the phenomena related to the inclusion of adamante derivatives and Volatils Organics Compounds (VOC), in the cavity of cyclodextrin, by the spectroscopic techniques of 2D NMR, CD and fluorescence. This study highlights the influence of chromophoric positioning, of these compounds, compared to their hydrophobic cavity. The complexation experiments have lead to the determination of sensitivity factors with respect to their guests, in aqueous solution, and to validate the "sensitive" aspect of these compounds. Finally, the use of molecular modeling, by molecular mechanistic and semi-empiricals methods, contributed to highlight the dynamic aspects related to the phenomena of complexation
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Granger, Devin B. "ACENES, HETEROACENES AND ANALOGOUS MOLECULES FOR ORGANIC PHOTOVOLTAIC AND FIELD EFFECT TRANSISTOR APPLICATIONS." UKnowledge, 2017. http://uknowledge.uky.edu/chemistry_etds/76.

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Polycyclic aromatic hydrocarbons composed of benzenoid rings fused in a linear fashion comprise the class of compounds known as acenes. The structures containing three to six ring fusions are brightly colored and possess band gaps and charge transport efficiencies sufficient for semiconductor applications. These molecules have been investigated throughout the past several decades to assess their optoelectronic properties. The absorption, emission and charge transport properties of this series of molecules has been studied extensively to elucidate structure-property relationships. A wide variety of analogous molecules, incorporating heterocycles in place of benzenoid rings, demonstrate similar properties to the parent compounds and have likewise been investigated. Functionalization of acene compounds by placement of groups around the molecule affects the way in which molecules interact in the solid state, in addition to the energetics of the molecule. The use of electron donating or electron withdrawing groups affects the frontier molecular orbitals and thus affects the optical and electronic gaps of the molecules. The use of bulky side groups such as alkylsilylethynyl groups allows for crystal engineering of molecular aggregates, and changing the volume and dimensions of the alkylsilyl groups affects the intermolecular interactions and thus changes the packing motif. In chapter 2, a series of tetracene and pentacene molecules with strongly electron withdrawing groups is described. The investigation focuses on the change in energetics of the frontier molecular orbitals between the base acene and the nitrile and dicyanovinyl derivatives as well as the differences between the pentacene and tetracene molecules. The differences in close packing motifs through use of bulky alkylsilylethynyl groups is also discussed in relation to electron acceptor material design and bulk heterojunction organic photovoltaic characteristics. Chapter 3 focuses on molecular acceptor and donor molecules for bulk heterojunction organic photovoltaics based on anthrathiophene and benzo[1,2-b:4,5-b’]dithiophene central units like literature molecules containing fluorene and dithieno[2,3-b:2’,3’-d]silole cores. The synthetic strategies of developing reduced symmetry benzo[1,2-b:4,5-b’]dithiophene to study the effect of substitution around the central unit is also described. The optical and electronic properties of the donors and acceptors are described along with the performance and characteristics of devices employing these molecules. The final two data chapters focus on new nitrogen containing polycyclic hydrocarbons containing indolizine and (2.2.2) cyclazine units. The optical, electronic and other physical properties of these molecules are explored, in addition to the synthetic strategies for incorporating the indolizine and cyclazine units. By use of alkylsilylethynyl groups, crystal engineering was investigated for the benzo[2,3-b:5,6-b’]diindolizine chromophore described in chapter 4 to target the 2-D “brick-work” packing motif for application in field effect transistor devices. Optical and electronic properties of the cyclazine end-capped acene molecules described in chapter 5 were investigated and described in relation to the base acene molecules. In both cases, density functional theory calculations were conducted to better understand unexpected optical properties of these molecules, which are like the linear acene series despite the non-linear attachment.
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Books on the topic "Indolizine"

1

Lee, Youngjun. Systematic Exploration of Indolizine-Based Small Fluorescent Molecules. Singapore: Springer Singapore, 2018. http://dx.doi.org/10.1007/978-981-13-1645-6.

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Jaecques, Ryan Patrick. Studies toward the synthesis of indolizidine alkaloids and analogues using ring-closing metathesis. Ottawa: National Library of Canada, 2003.

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Lee, Youngjun. Systematic Exploration of Indolizine-Based Small Fluorescent Molecules: Synthesis, Analysis and Application. Springer, 2018.

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Lee, Youngjun. Systematic Exploration of Indolizine-Based Small Fluorescent Molecules: Synthesis, Analysis and Application. Springer, 2018.

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Book chapters on the topic "Indolizine"

1

Lee, Youngjun. "Introduction." In Systematic Exploration of Indolizine-Based Small Fluorescent Molecules, 1–20. Singapore: Springer Singapore, 2018. http://dx.doi.org/10.1007/978-981-13-1645-6_1.

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Lee, Youngjun. "A Comprehensive Studies of an Indolizine-Based Seoul-Fluor System." In Systematic Exploration of Indolizine-Based Small Fluorescent Molecules, 21–42. Singapore: Springer Singapore, 2018. http://dx.doi.org/10.1007/978-981-13-1645-6_2.

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Lee, Youngjun. "Tetrazine-Containing Colorful Bioorthogonal Probes Based on the Indolizine Core Skeleton." In Systematic Exploration of Indolizine-Based Small Fluorescent Molecules, 43–84. Singapore: Springer Singapore, 2018. http://dx.doi.org/10.1007/978-981-13-1645-6_3.

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Lee, Youngjun. "Rational Development of Furoindolizine Core Skeleton Guided by Oscillator Strength." In Systematic Exploration of Indolizine-Based Small Fluorescent Molecules, 85–121. Singapore: Springer Singapore, 2018. http://dx.doi.org/10.1007/978-981-13-1645-6_4.

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Blewitt, H. L. "Indolizine and Aza Derivatives With Additional Nitrogens in the 5-Membered Ring." In Chemistry of Heterocyclic Compounds: A Series Of Monographs, 117–78. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2008. http://dx.doi.org/10.1002/9780470187005.ch2.

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Brandi, Alberto, Francesca Cardona, Stefano Cicchi, Franca M. Cordero, and Andrea Goti. "Enantiopure Pyrroline-N-Oxides for the Synthesis of Pyrrolizine and Indolizine Alkaloids." In Current Trends in Organic Synthesis, 213–20. Boston, MA: Springer US, 1999. http://dx.doi.org/10.1007/978-1-4615-4801-0_27.

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Shelke, R. N., A. B. Kanagare, S. U. Deshmukh, S. R. Bembalkar, D. N. Pansare, Keshav Lalit Ameta, and R. P. Pawar. "An Overview of the Synthesis of Pyrroline, Indolizine, and Quinolizinium Derivatives Using Different Nanocatalysts." In Nanocatalysis, 53–74. New York: CRC Press, 2022. http://dx.doi.org/10.1201/9781003141488-3.

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Babaev, Eugene V. "Fluorinated Indolizines." In Fluorine in Heterocyclic Chemistry Volume 1, 157–80. Cham: Springer International Publishing, 2014. http://dx.doi.org/10.1007/978-3-319-04346-3_4.

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Seigler, David S. "Pyrrolizidine, Quinolizidine, and Indolizidine Alkaloids." In Plant Secondary Metabolism, 546–67. Boston, MA: Springer US, 1998. http://dx.doi.org/10.1007/978-1-4615-4913-0_30.

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Sahoo, Basudev. "Transition Metal Free Visible Light-Mediated Synthesis of Polycyclic Indolizines." In Visible Light Photocatalyzed Redox-Neutral Organic Reactions and Synthesis of Novel Metal-Organic Frameworks, 81–107. Cham: Springer International Publishing, 2016. http://dx.doi.org/10.1007/978-3-319-48350-4_4.

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Conference papers on the topic "Indolizine"

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Ciorteanu, Roxana Elena, Monica Sardaru, Dumitrela Diaconu, Ionel Mangalagiu, and Ramona Danac. "Synthesis and anticancer properties of new indolizinic derivatives." In Scientific seminar with international participation "New frontiers in natural product chemistry". Institute of Chemistry, Republic of Moldova, 2023. http://dx.doi.org/10.19261/nfnpc.2023.ab25.

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Natural compounds with indolizine scaffolds have demonstrated numerous biological activities and have found use in medical research laboratories. Thys, the unique indolizine scaffold became an important system for the development of new drug candidates in medicinal chemistry. [1,2] Several indolizines with excellent anticancer activity and tubulin polymerization inhibitory potency have been reported recently, and our group contributed also to the field. [1,3] The goal of this study was the design, synthesis and anticancer evaluation of several new derivatives with symmetrical or unsymmetrical substituted 7,7’-(ethene-1,2-diyl)bisindolizine structure, and several new 6-, 7- or 8-substituted indolizine derivatives. Mono and bisindolizines were synthesized in good yields via [3+2] dipolar cycloaddition of the in situ generated ylides, from corresponding N-pyridinium salts to ethyl propiolate. Part of the new derivatives were tested for their anticancer activity by screening against NCI’s 60 human tumour cell lines panel and the results are presented herein. In vitro experiments regarding tubulin interaction were performed for the active compounds.
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Yang, Zhen, Yefei Wang, Matjaž Finšgar, Jiajia Wu, and Wengang Ding. "Novel High-Efficient Key Component of Steel Corrosion Inhibitors Formulation for Acidification: Indolizine Derivatives of the Conventional N-Heterocyclic Quaternary Ammonium Salts." In SPE International Conference on Oilfield Chemistry. SPE, 2023. http://dx.doi.org/10.2118/213814-ms.

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Abstract Acidizing, the widely used technique for well stimulation, requires a great consumption of effective Corrosion Inhibitors (CIs), due to the severe and fast corrosion of metallic equipment caused by strong hot acid as soon as the acidizing fluids are pumping down to reservoir. This paper presents a new concept of indolizine derivative inhibitors with remarkable inhibition effectiveness for steel under acidizing condition, which will reduce the cost and environmental burden of acidizing CIs significantly. Indolizine derivatives of several quinolinium salts (serves as main component of currently used acidizing CIs) were synthesized respectively through an optimized mild procedure from quinoline and different halides. The inhibition of the new inhibitors for N80 steel were evaluated in hot 15 wt.% HCl by gravimetric and electrochemical analysis, while their corrosion prevention mechanism were studied. Surface adsorption and thermodynamic aspect of inhibition process were also investigated. Synergistic inhibition performances of the indolizine derivatives with surfactant, KI and other additives were examined. For the synthesis step, a relatively high yield of the crude products were reported. Inhibition assessment results showed that compared with their quinolinium salt precursors, the dimer derivative can dramatically mitigate the corrosion speed and exhibit considerable inhibition efficiencies even at an extremely low dosage. The results obtained from gravimetric tests, electrochemical methods as well as the surface analysis are in good agreement and confirmed the well-behaved anti-corrosion properties of the derivatives. Conclusion from biotoxicity experiments showed that compared with their precursor quinolinium salts, both the indolizine derivatives and the original quinolinium salts share almost the same EC50 values, revealing the advantages in eco-friendly aspect. Mechanism study reveals that the new compounds can be characterized as cationic "mixed type" and the special molecular structure (conjugated aromatic moiety) may contribute a lot to their remarkable inhibition. Besides, the studied dimer derivatives also presents a good solubility and thermo-stability in acid solution. The amazing synergistic inhibition of indolizine derivative obviously shows that the inhibitive mixture could be utilized as new effective CI for acidizing. The inhibition of conventional quinoline salts CIs would get greatly updated after been converted to their indolizine dimer derivatives. This provides a smart solution for exploring innovative acidizing CI with better protection efficiency. The use of indolizine derivatives may largely minimize the total amount as well as the total expenses of CIs in acidizing fluids and showing good prospects in replacement of the current main components of acidizing CIs in the near future.
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Yang, Zhen, Yefei Wang, Matjaž Finšgar, Huayou Hu, Jiajia Wu, Fengtao Zhan, Shuangqing Sun, and Wengang Ding. "Novel High-Effective Component for Acidizing Corrosion Inhibitors: Indolizine Derivatives of the Quaternary Quinolinium Salts." In SPE Asia Pacific Oil & Gas Conference and Exhibition. Society of Petroleum Engineers, 2020. http://dx.doi.org/10.2118/202369-ms.

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Yang, Zhen, Yefei Wang, Renzhuo Wang, Wuhua Chen, Mingchen Ding, Fengtao Zhan, and Baofeng Hou. "Insight of New Eco-Friendly Acidizing Corrosion Inhibitor: Structure and Inhibition of the Indolizine Derivatives." In SPE International Conference on Oilfield Chemistry. Society of Petroleum Engineers, 2019. http://dx.doi.org/10.2118/193555-ms.

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Wang, Renzhuo, Zhen Yang, Wuhua Chen, Yefei Wang, Mingchen Ding, and Fengtao Zhan. "Structure and Inhibition of the Indolizine Derivative: New Concept of High-Efficient Corrosion Inhibitors for Acidizing." In International Petroleum Technology Conference. International Petroleum Technology Conference, 2019. http://dx.doi.org/10.2523/19413-ms.

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Wang, Renzhuo, Zhen Yang, Wuhua Chen, Yefei Wang, Mingchen Ding, and Fengtao Zhan. "Structure and Inhibition of the Indolizine Derivative: New Concept of High-Efficient Corrosion Inhibitors for Acidizing." In International Petroleum Technology Conference. International Petroleum Technology Conference, 2019. http://dx.doi.org/10.2523/iptc-19413-ms.

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Wang, Yefei, Zhen Yang, Renzhuo Wang, Wuhua Chen, Mingchen Ding, Fengtao Zhan, and Baofeng Hou. "High-efficiency Corrosion Inhibitor for Acidizing: Synthesis, Characterization and Anti-corrosion Performance of Novel Indolizine Derivative." In SPE International Conference on Oilfield Chemistry. Society of Petroleum Engineers, 2019. http://dx.doi.org/10.2118/193587-ms.

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Shalin, N. I., O. D. Fominykh, A. A. Kalinin, and M. Yu Balakina. "Molecular modeling in design of nonlinear-optical polymer materials doped with indolizine chromophores with isolating groups in donor and acceptor moieties." In ACTUAL PROBLEMS OF ORGANIC CHEMISTRY AND BIOTECHNOLOGY (OCBT2020): Proceedings of the International Scientific Conference. AIP Publishing, 2022. http://dx.doi.org/10.1063/5.0069653.

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Amaral, Mônica F. Z. J., Amanda A. Baumgartner, and Giuliano C. Clososki. "Base/Electrophile-Controlled Regioselective Functionalization of 1-Substituted-Indolizines." In 15th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-bmos2013_2013912181622.

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Bertonha, Ariane F., and Antonio C. B. Burtoloso*. "Studies aiming the synthesis of the indolizidine alkaloids (+)-Ipalbidine and (+)-Antofine." In 15th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-bmos2013_201391415130.

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