Relevant bibliographies by topics / Spiro compound

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  2. Dissertations / Theses
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Academic literature on the topic 'Spiro compound'

Author: Grafiati
Published: 20 April 2024

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Journal articles on the topic "Spiro compound"

1

DANSHPAJUH, Marjan, and Neda HASANZADEH. "Study of influence of anomeric effect on conformational preferences using hybrid density functional theory (DFT) and natural bond orbital (NBO) interpretation." Revue Roumaine de Chimie 68, no. 1-2 (January 17, 2023): 61–74. http://dx.doi.org/10.33224/rrch.2023.68.1-2.06.

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For the relationship between thermodynamic parameters, global hardness, global electronegativity, anomeric effect, structural parameters, and structural properties of dodecahedro-spiro [isochromene-3,2'-pyran] (A), dodecahedro-spiro [isothiocromene-3,2'- thiopyran) (B), dodecahedro-spiro [isochroman-3,2'-thiopyran] (C) and dodecahedro-spiro [isothiochrome-3,2'-pyran] (D) computational methods (B3LYP / 6-311 ++ G **) were used. Results show that the calculated Gibbs free energy and enthalpy differences between the axial- and equatorial- stereoisomers [i.e. ΔG = Geq – Gax, ΔH = Heq- Hax] decrease from compound A to compound B and from compound C to compound D. NBO results show that the anomeric effect associated with the electron delocalization is in benefit of the axial-stereoisomers and with the decrease of the anomeric effect, the values of global hardness (η), and global electronegativity (χ), from compound A to compound B and from compound C to Composition D is also decrease. The correlations between the global hardness, global electronegativity, anomeric effect, structural parameters, and thermodynamic parameters [ΔH, ΔG, and ΔS] of compounds A-D have been investigated. Also, it can be concluded that the stability energy obtained from the numerical values of the anomeric effect and the values calculated theoretically (B3LYP / 6-311 ++ G **) confirmed each other.
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Tripathi, Rahul R., and Ratnamala P. Sonawane. "An Extraction of the Isatin from the Couroupita guianesis (Cannon Ball Tree) and a Novel Synthesis of the N,N'-(2-oxo-3'H-spiro[indoline-3,2'-[1,3,4]thiadiazole]-3',5'-diyl]diacetamidefrom the Isatin." International Letters of Chemistry, Physics and Astronomy 15 (September 2013): 119–25. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.15.119.

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Isatins are synthetically versatile substrates, where they can be used for the synthesis of a large variety of Isatins and heterocyclic compounds. In this, the isatin were extracted from the floral material of Couroupita guianesis commonly known as an Cannon ball tree. After that, a novel heterocyclic spiro derivative having an IUPAC name N,N’-(2-oxo-3’H-spiro[indoline-3,2’-[1,3,4] thiadiazole]-3’5’-diyl)diacetamide were synthesized , which may be used as raw material for drug synthesis. A spiro compound N,N’-(2-oxo-3’H-spiro[indoline-3,2’-[1,3,4] thiadiazole]-3’5’-diyl)diacetamide were synthesise by refluxing Isatin and thiosemicarbazone in ethanol and then on heating with acetic anhydride underwent to cyclization into intermediate that on acetylation of the NH and NH2 groups afforded the spiro compound.
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Tripathi, Rahul R., and Ratnamala P. Sonawane. "An Extraction of the Isatin from the <i>Couroupita guianesis</i> (Cannon Ball Tree) and a Novel Synthesis of the N,N'-(2-oxo-3'H-spiro[indoline-3,2'-[1,3,4]thiadiazole]-3',5'-diyl]diacetamidefrom the Isatin." International Letters of Chemistry, Physics and Astronomy 15 (June 29, 2013): 119–25. http://dx.doi.org/10.56431/p-h7k957.

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Isatins are synthetically versatile substrates, where they can be used for the synthesis of a large variety of Isatins and heterocyclic compounds. In this, the isatin were extracted from the floral material of Couroupita guianesis commonly known as an Cannon ball tree. After that, a novel heterocyclic spiro derivative having an IUPAC name N,N’-(2-oxo-3’H-spiro[indoline-3,2’-[1,3,4] thiadiazole]-3’5’-diyl)diacetamide were synthesized , which may be used as raw material for drug synthesis. A spiro compound N,N’-(2-oxo-3’H-spiro[indoline-3,2’-[1,3,4] thiadiazole]-3’5’-diyl)diacetamide were synthesise by refluxing Isatin and thiosemicarbazone in ethanol and then on heating with acetic anhydride underwent to cyclization into intermediate that on acetylation of the NH and NH2 groups afforded the spiro compound.
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4

Hafez, Hend N., Abdel-Rhman B. A. El-Gazzar, and Magdi E. A. Zaki. "Simple approach to thieno[3,2-d]pyrimidines as new scaffolds of antimicrobial activities." Acta Pharmaceutica 66, no. 3 (September 1, 2016): 331–51. http://dx.doi.org/10.1515/acph-2016-0029.

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Abstract 6ʹ-(4-Chlorophenyl)-spiro[cyclohexane-1,2ʹ-thieno[3,2-d][1,3] oxazin]-4ʹ(1ʹH)-one (1) was synthesized and used as a starting material for the synthesis of a novel series of spiro compounds having biologically active sulfonamide 2a-e and 3ʹ-(4-acetylphenyl)-6ʹ- (4-chlorophenyl)-1ʹH-spiro[cyclohexane-1,2ʹ-thieno[3,2-d] pyrimidine-4ʹ(3ʹH)-one (3). Compound 2a was used as a key intermediate for the synthesis of sulfonyl carbothioamide derivatives 4a-c. Also, compound 3 was used as an intermediate for the synthesis of 3ʹH-spiro[cyclohexane-1,2ʹ-thieno[3,2-d]pyrimidin]-3ʹ-yl] phenyl}-2-imino-4-(substituted phenyl and/or thienyl)-1,2-dihydropyridine- 3-carbonitrile derivatives 5a-e, 3ʹH-spiro[cyclohexane- 1,2ʹ- thieno[3,2-d]pyrimidin]-3ʹ-yl]phenyl}-2-oxo-4-(substituted phenyl and/or thienyl)-1,2-dihydropyridine-3-carbonitrile derivatives 6a-e, and 4-[(2Z)-3-substituted-arylprop-2-enoyl] phenyl-1ʹH-spiro[cyclohexane-1,2ʹ-thieno[3,2-d]pyrimidine derivatives 7a-e. Cyclocondensation of 7a-e with hydrazine hydrate produced 6ʹ-(4-chlorophenyl)-3ʹ-[4-(5-substituted aryl-4,5-dihydro- 1H-pyrazol-3-yl)phenyl]-1ʹH-spiro[cyclohexane-1,2ʹ-thieno- [3,2-d]pyrimidin]-4ʹ(3ʹH)-ones 8a-e but with hydroxylamine hydrochloride afforded the corresponding isoxazoline derivatives 9a-e. Also, cyclocondensation by thiourea afforded 2-thioxo-1,2- dihydropyrimidin-4-yl)-phenyl-spiro-{cyclohexanethieno[3,2-d] pyrimidin}-4-one derivatives 10a-e. The new compounds were investigated for antimicrobial activity. Compounds 2c, 8b,c, 9b and 10b were the most potent ones against both Gram-negative and Gram-positive bacteria. Compound 8c exhibited higher antifungal activity towards the examined fungi with MIC of 1-2 μmol mL-1 compared to ketoconazole (MIC 2-3 μmol mL-1 ).
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Macháček, Vladimír, Makky M. M. Hassanien, and Vojeslav Štěrba. "Kinetics and mechanism of spiro adduct formation from and smiles rearrangement of N-methyl-N-(2,4,6-trinitrophenyl)aminoacetanilide. Base-catalyzed transformation of N-(2,4,6-trinitrophenylamino)acetanilide into 2-nitroso-4,6-dinitroaniline." Collection of Czechoslovak Chemical Communications 52, no. 9 (1987): 2225–40. http://dx.doi.org/10.1135/cccc19872225.

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The paper deals with kinetics and mechanism of the reaction of N-(2,4,6-trinitrophenyl)aminoacetanilide (IIa) with methoxide ion and with the reaction kinetics and product structure of the reaction of N-methyl-N-(2,4,6-trinitrophenyl)aminoacetanilide (IIb) in methanolic buffers. The main product of the reaction of compound IIa with methoxide is 2-nitroso-4,6-dinitroaniline along with about 3% spiro adduct. The dependence of the experimental rate constant kexp of the reaction with methoxide on the methoxide concentration is similar to that of the reaction of N-(2,4,6-trinitrophenyl)glycine methylamide, however, compound IIa reacts about 2·5 times faster and produces the spiro adduct in an about four times smaller amount. In basic acetate buffers, compound IIb is transformed quantitatively into the spiro adduct. In chloroacetate buffers, the reverse ring opening of the spiro adduct prevails. The ring opening takes two ways: A specific acid catalyzed one and a non-catalyzed one. Corresponding therewith is the non-catalyzed and specific base catalyzed formation of the spiro adduct. In aniline-anilinium chloride buffers, equilibrium is rapidly established between the spiro adduct and 2-methylamino-N-phenyl-N-(2,4,6-trinitrophenyl)acetamide hydrochloride. The mixture of the two compounds is transformed gradually into compound IIb which shows the highest thermodynamic stability in the given medium. At [H+] > 10-3 mol l-1 the thermodynamically most stable species is 2-methylamino-N-phenyl-N-(2,4,6-trinitrophenyl)acetamide hydrochloride.
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Nakano, Koji, Ko Takase, and Keiichi Noguchi. "Furan-Containing Chiral Spiro-Fused Polycyclic Aromatic Compounds: Synthesis and Photophysical Properties." Molecules 27, no. 16 (August 11, 2022): 5103. http://dx.doi.org/10.3390/molecules27165103.

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Spiro-fused polycyclic aromatic compounds (PACs) have received growing interest as rigid chiral scaffolds. However, furan-containing spiro-fused PACs have been quite limited. Here, we design spiro[indeno[1,2-b][1]benzofuran-10,10′-indeno[1,2-b][1]benzothiophene] as a new family of spiro-fused PACs that contain a furan unit. The compound was successfully synthesized in enantiopure form and also transformed to its S,S-dioxide derivative and the pyrrole-containing analog via aromatic metamorphosis. The absorption and emission properties of the obtained furan-containing chiral spiro-fused PACs are apparently different from those of their thiophene analogs that have been reported, owing to the increased electron-richness of furan compared to thiophene. All of the furan-containing chiral spiro-fused PACs were found to be circularly polarized luminescent materials.
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Konyar, Dilan, Cenk A. Andac, and Erdem Buyukbingol. "Design, Synthesis and Cytotoxic Activity of Spiro(oxindole-3-3'- pyrrolidine) Derivatives." Letters in Drug Design & Discovery 15, no. 1 (January 3, 2018): 37–45. http://dx.doi.org/10.2174/1570180814666170810120634.

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Background: Spiro[pyrrolidine-3,3'-oxindole] compounds are reported to be highly bioactive natural and synthetic products. Initially, spirooxindole alkaloids were isolated from plants of the Apocynaceae and Rubiaceae families, which were found to have a common scaffold, spiro[pyrrolidine-3,3'-oxindole], exhibiting anticancer activities., we specifically aimed at the synthesis, characterization and anticancer activity of novel spiro[pyrrolidine-3,3' -oxindole] derivatives, compounds 6a-c and 7. Methods: The synthesis was initiated by Knovenegal condensation of indole-2-one with an appropriate benzaldehyde in presence of piperidine to afford compounds 3a-c. Compounds 6a-c were synthesized by an asymmetric 1,3-dipolar cycloaddition between compounds 3a-c and (2S, 3R)-2, 3, 5, 6-tetrahydro-2, 3-diphenyl-1, 4-oxazin-6-one, which is an intermediate compound formed by the Schiff base reaction between 3-methyl-butanal and (2S, 3R)-2, 3, 5, 6-tetrahydro-2, 3-diphenyl- 1,4-oxazin-6-one, in presence of molecular sieves (4Å) under argon atmosphere. Compound 6a was then reacted with ethylamine-HCl in THF at room temperature to yield compound 7. Results: Cytotoxic effects of the compounds synthesized were determined on Huh7, MV, HCT116 and MCF7 cancer cell lines by the NCI-60 Sulforhodamine B Assay, using (S)-(+)-Camptothecin as a positive control. In general, target compounds showed better cytotoxic activities against the MCF7 and HCT116 cancer cell lines. It was found that compound 7 exhibited the most potent inhibitory activity with IC50 values of 4.8 µM, 3.9 µM, 14.9 µM and 8.2 µM against the MCF7, HCT116, MV and Huh7 cell lines, respectively. Conclusion: It was determined that compounds 6a&6b possess C6'(S)|C8'(R)|C9'(R) stereochemistry and compound 7 adopts C2'(S)|C4'(R)|C5'(R) stereochemistry. Cytotoxicity studies suggest that compound 7 gave rise to the highest anticancer activity against MCF7, HCT116, and Huh7 cancer cell lines.
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Barakat, Assem, Mohammad Shahidul Islam, M. Ali, Abdullah Mohammed Al-Majid, Saeed Alshahrani, Abdullah Saleh Alamary, Sammer Yousuf, and M. Iqbal Choudhary. "Regio- and Stereoselective Synthesis of a New Series of Spirooxindole Pyrrolidine Grafted Thiochromene Scaffolds as Potential Anticancer Agents." Symmetry 13, no. 8 (August 4, 2021): 1426. http://dx.doi.org/10.3390/sym13081426.

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A series of new spiro-heterocycles engrafted spirooxindole/pyrrolidine/thiochromene scaffolds was synthesized by the three-component 1,3-dipolar cycloaddition reactions in a fully controlled regio- and stereo-selective fashion. Condensation of several substituted isatin derivatives with L-proline generated the azomethine ylides which subsequently reacted with chalcones based thiochromene scaffold, and finally afforded the target spiro-compounds. This simple protocol furnished a structurally complex, biologically relevant spiro-heterocycles in good yields through a one-pot process. All synthesized chalcone-based thiochromene, along with the spirooxindole/pyrrolidine/thiochromene scaffolds, were tested for their anticancer activity against four cancer cell lines (PC3, HeLa, MCF-7, and MDA-MB231). Toxicity of these compounds was also evaluated against human fibroblast BJ cell line, and they appeared to be not cytotoxic. For the prostate cancer (PC3) cell line, the most active hybrid, among synthesized series, was compound (7f, IC50 = 8.7 ± 0.7 µM). The most potent spirooxindole/pyrrolidine/thiochromene hybrid against cervical (HeLa) cancer cells was compound (7k, IC50 = 8.4 ± 0.5 µM) having chlorine and p-trifluoromethyl substituents attached to phenyl rings. Finally, against the MCF-7 and MDA-MB231 breast cancer cell lines, compound (7d) was the most active member of this series (IC50 = 7.36 ± 0.37, and 9.44 ± 0.32 µM, respectively).
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Westphal, Regina, Eclair Venturini Filho, Laiza Bruzadelle Loureiro, Cláudio Francisco Tormena, Claudia Pessoa, Celina de Jesus Guimarães, Mariana Palmeira Manso, et al. "Green Synthesis of Spiro Compounds with Potential Anticancer Activity through Knoevenagel/Michael/Cyclization Multicomponent Domino Reactions Organocatalyzed by Ionic Liquid and Microwave-Assisted." Molecules 27, no. 22 (November 19, 2022): 8051. http://dx.doi.org/10.3390/molecules27228051.

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In this work a microwave-assisted Knoevenagel/Michael/cyclization multicomponent domino methodology, using ethanol as solvent and the ionic liquid 1-methylimidazolium chloride as catalyst was developed for the synthesis of spiro compounds. The reaction conditions considered ideal were determined from a methodological study varying solvent, catalyst, amount of catalyst, temperature, and heating mode. Finally, the generality of the methodology was evaluated by exploring the scope of the reaction, varying the starting materials (isatin, malononitrile, and barbituric acid). Overall, the twelve spiro compounds were synthesized in good yields (43–98%) and the X-ray structure of compound 1b was obtained. In addition, the in vitro antiproliferative activities of the spirocycles against four types of human cancer cell lines including HCT116 (human colon carcinoma), PC3 (prostate carcinoma), HL60 (promyelocytic leukemia), and SNB19 (astrocytoma) were screened by MTT-based assay. It is noteworthy that spiro compound 1c inhibited the four cell lines tested with the lowest IC50 values: 52.81 µM for HCT116, 74.40 µM for PC3, 101 µM for SNB19, and 49.72 µM for HL60.
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Wu, Mengyao, Yilin Wang, Xiaojun Tan, and Jinsong Gu. "Theoretical study on the reaction between phosphacyclopropenylidene and ethylene: An alternative approach to the formation of phosphorus-bearing heterocyclic compound." Journal of the Serbian Chemical Society 85, no. 9 (2020): 1175–84. http://dx.doi.org/10.2298/jsc191217026w.

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The reaction mechanism between phosphacyclopropenylidene and ethylene has been systematically investigated at the B3LYP/6-311++G(d,p) level of theory in order to better understand the reactivity of unsaturated cyclic phosphorus-bearing carbene. Geometry optimizations and vibrational analyses have been performed for the stationary points on the potential energy surface of the system. Calculations show that the spiro bicyclic intermediate could be produced through the cycloaddition process between phosphacyclopropenylidene and ethylene initially. The reaction mechanism is illustrated with the frontier molecular orbital theory. Introduction of electron-withdrawing group in phosphacyclopropenylidene will better facilitate the addition process. Through subsequent ring-expanding and hydrogen-migrating process, fuse-ring and allene compounds could be produced, respectively. Furthermore, it?s easy for spiro bicyclic intermediate and another ethylene to form a spiro tricyclic compound. This study is helps to understand the reactivity of phosphacyclopropenylidene, the evolution of phosphorus-bearing molecules in space, and to offer an alternative approach to the formation of phosphorus-bearing heterocyclic compound.
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Dissertations / Theses on the topic "Spiro compound"

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Brouillac, Clément. "Systèmes π-conjugués donneur-accepteur : composés spiro et nano anneaux pour des diodes organiques électrophosphorescentes." Electronic Thesis or Diss., Université de Rennes (2023-....), 2023. http://www.theses.fr/2023URENS097.

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L’électronique organique (EO) s’articule autour de l’utilisation des semi-conducteurs organiques (SCOs). Les diodes organiques électroluminescentes (OLEDs) font partie des technologies électroniques les plus matures et sont déjà présentes dans nos smartphones, ordinateurs et téléviseurs. Durant cette thèse, nous nous sommes particulièrement intéressés à l’élaboration de matrices hôtes pour la seconde génération d’OLEDs : les diodes organiques électrophosphorescentes (PhOLEDs). Deux design moléculaires différents ont été conçus avec deux objectifs différents. Le premier objectif consiste à développer de nouvelles matrices hôtes utilisant l’architecture Donneur-spiro-Accepteur pour des PhOLEDs monocouches, qui sont des dispositifs simplifiés utilisant seulement les électrodes et la couche émissive. Ces travaux ont conduit à la fabrication de PhOLEDs monocouches des trois couleurs présentes dans un pixel (rouge, vert et bleu), et des couleurs pour l’éclairage (jaune et blanc). Des records de performances ont été obtenus. Le deuxième objectif consiste à développer de nouveaux SCOs appelés nano-anneaux. Après un chapitre bibliographique analysant les performances des nano-anneaux en EO, nous présenterons une étude de structure/propriétés de nano-anneaux donneur-accepteur. Ces travaux, nous ont permis de mieux comprendre les propriétés singulières de ces composés cycliques à base de carbazoles, qui ont ensuite ont été incorporés dans des PhOLEDs multicouches pour évaluer leurs performances en tant que matrice hôtes. Ces travaux représentent les premiers exemples du domaine
Organic electronics (EO) is based on organic semiconductors (OSCs). Organic light-emitting diodes (OLEDs) are among the most mature EO technologies and are already present in our smartphones, computers and televisions. During this thesis, we were particularly interested in the development of host materials for the second generation of OLEDs: organic electrophosphorescent diodes (PhOLEDs). Two different molecular designs have been elaborated with two different objectives. The first objective was to develop new host materials using the Donor-spiro-Acceptor architecture for single-layer PhOLEDs, which are simplified devices using only the electrodes and the emissive layer. This work has enabled the fabrication of single-layer PhOLEDs in the three colours present in a pixel (red, green and blue) and in the colours used for lighting (yellow and white). Device performance records have been obtained. The second objective was to develop new SCOs, with a cylindric shape, called nanohoops. After a bibliographic chapter analysing the performance of nanohoops in EO, we present a structure/properties study of Donor-Acceptor nanohoops. This work enabled us to gain a better understanding of the unique properties of these carbazole-based nanohoops, which were then incorporated into multilayer PhOLEDs to measure their performances. This work provides the first exemples of the field
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Kowada, Toshiyuki. "Studies on Synthesis and Properties of Heteroarene-Containing π-Conjugated Compounds Having Spirofluorene Moieties." 京都大学 (Kyoto University), 2010. http://hdl.handle.net/2433/120879.

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Mohammed, Shahid. "Manganese (3) acetate oxidative free radical cyclisations : the synthesis of novel functionalised spiro and fused acetal compounds." Thesis, University of Southampton, 1993. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.317645.

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Dalinot, Clément. "Synthèse de composés spiro pour l'électronique plastique : relations structure-propriétés." Thesis, Angers, 2016. http://www.theses.fr/2016ANGE0070.

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De par leur versatilité synthétique, les matériaux moléculaires pour l’électronique ou la photonique organique peuvent être conçus sur mesure afin d'intégrer, de façon optimale, divers types de dispositifs. Dans ce contexte, ces travaux de thèse se sont consacrés à l'élaboration et l'étude de composés spiro pour des applications en électronique organique. Ainsi, après un premier chapitre introductif présentant un état de l’art focalisé sur l'utilisation des composés spiro au sein de dispositifs électroniques, les deux autres chapitres seront consacrés à l'élaboration et la mise en oeuvre de nouvelles molécules organiques comportant un coeur spiro. En conséquence, le chapitre 2 sera entièrement consacré à la synthèse des molécules cibles envisagées. Il reprendra donc la fonctionnalisation d’un composé spiro largement étudié : le spirobifluorène, ainsi que les synthèses décrites de certains de ses analogues bi-hétérocycliques, et les optimisations apportées. Enfin, la présentation d'une nouvelle méthodologie de synthèse de composés à coeur spiro à partir de bis-arylcétone sera exposée et rationalisée grâce à une approche théorique. Le chapitre 3, quant à lui, rassemblera l'ensemble des caractérisations des propriétés physico-chimiques des composés préparés afin de pouvoir dégager certaines règles d'ingénierie moléculaire. De plus, la caractérisation de dispositifs électroniques incorporant nos molécules comme matériaux actifs nous permettra de mettre en avant les avantages des molécules à coeur spiro par rapport à leurs analogues linéaires
In organic electronics or photonics field, the molecular materials can be elaborated on fashion in order due to their synthetic versatility which represents a strong advantage for their optimal integration in corresponding devices. In this context, this thesis work was devoted to the development and study of spiro compounds for organic electronics applications. After a first opening chapter focusing on the state of the art of various uses of spiro compounds in molecular electronic, the two following chapters are devoted to the development and implementation of new organic molecules including a spiro node. Therefore, chapter 2 is completely devoted to the synthesis of envisioned target molecules. It resumes the functionalisation of a well-spread spiro compound: the spirobifluorene, as well as the optimized synthesis of some previously described bi-heterocyclic analogs. Finally, the presentation of a new synthesis methodology starting form bis-aryl ketones is exposed and streamlined with a theoretical approach. Concerning the chapter 3, it collects all physicochemical characterizations of the prepared compound in order to emit some simple molecular engineering rules. Moreover, the characterization of electronic devices incorporating our molecules as active materials allow us to highlight the benefits of spiro molecules by comparison to their linear analogs
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CRISTOFARO, Dario. "Simultaneous recovery of cellulose and other value-added compounds from orange waste & Synthesis of spiro and ureidic compounds for modulation studies of mptp protein." Doctoral thesis, Università degli studi di Ferrara, 2017. http://hdl.handle.net/11392/2487943.

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This thesis is divided in two separate sections, both conducted in the Department of Chemical and Pharmaceutical Sciences under the supervision of Prof. Dr. Simonetta Benetti and Prof. Dr. Claudio Trapella. The first project aimed to demonstrate the opportunity of utilizing a new type of citrus waste, called decanter centrifuge orange waste (DCOW), to extract cellulose and other constituents of the matrix. These could be sold as either mixture or isolated compounds (or derivatives) thus avoiding environmental dangerous waste disposal. A sequence of extraction steps and pH-dependant treatments were studied in order to isolate five different products from DCOW. The choice of the solvents used for extraction was directed by economic issues as well as by the need to attain food-grade compounds. An acidic treatment was utilized in order to isolate a pectic fraction, while a basic treatment allowed purifying the cellulose fraction. α-Cellulose was successfully isolated (with a yield of 9.81% ± 0.25 on dry basis) and used to produce cellulose acetate, a well-known commercial product. The other isolated fractions were analytically characterized and consisted of polyphenols, carbohydrates and terpenes, which represent all high-value products whose further purification may results in appealing saleable products. The second project was intended to synthesize potential inhibitors of mitochondrial permeability transition pore (mPTP) complex opening, which is known to be responsible for ischemic-reperfusion injury (IRI). Up to now, only few compounds are known to directly inhibit this complex. Of them, dicyclohexylcarbodiimide (DCC) and oligomycin A were elected as drug design starting points. Since DCC is slowly hydrated in human body to form dicyclohexylurea (DCU), the latter was chosen as the real starting reference substrate for the synthesis of the target compounds. Therefore, symmetric and asymmetric ureas and thioureas were produced. Besides, some aliphatic carbamate derivatives were synthesized to better understand the influence of the rings adjacent to the carbonyl group on biological activities. Studies were also conducted to synthesize new spiro compounds mimicking oligomycin A structural core. In this case, 1-phenyl-1, 3, 8-triaza-spiro[4,5]decan-4-one template was used to produce the corresponding N-8 substituted derivatives. Almost all these derivatives were produced in reasonably high yields, using inexpensive reagents and under rather mild reaction conditions. Noticeably, preliminary results from biological characterization showed that these derivatives have both inhibitor and activator potency against mPTP opening. While the identified inhibitors may be useful for IRI treatments, alternative use of the activators as antitumor compounds was hypothesized.
Questa tesi è divisa in due progetti distinti, entrambi condotti al Dipartimento di Chimica e Scienze Farmaceutiche e sotto la supervisione della professoressa Simonetta Benetti e del professor Claudio Trapella. Il primo progetto mira a dimostrare l’opportunità di utilizzare un nuovo tipo di rifiuto agrumicolo, chiamato residuo d’arancia della centrifuga decanter (decanter centrifuge orange waste – DCOW), per estrarre la cellulosa e altri costituenti presenti all’interno matrice organica. Quest’ultimi potrebbero essere venduti sia come miscele complesse che come composti purificati (o derivati), al fine di ridurre l’impatto ambiente derivante dal progressivo deposito dello scarto agrumicolo. Sono stati studiati differenti approcci al problema, tra cui una sequenza di estrazioni con solventi organici e trattamenti a differente pH al fine di isolare cinque differenti frazioni. I solventi utilizzati durante le estrazioni sono stati selezionati tenendo in considerazione l’ipotetico costo industriale e la necessità di ottenere dei composti che potessero essere destinati anche ad un uso alimentare. Un trattamento acido è stato invece necessario per rimuovere ed isolare una frazione pectica, mentre il trattamento basico ha permesso di purificare la frazione cellulosica. Infine, l’α-cellulosa ottenuta (con una resa del 9.81 % ± 0.25 rispetto al peso secco della matrice) è stata utilizzata per produrre l’acetato di cellulosa, un noto prodotto di interesse commerciale. Nelle altre frazioni isolate, caratterizzate dal punto di vista analitico, è stata riscontrata la presenza di polifenoli, carboidrati e terpeni, tutti composti ad alto valore aggiunto, la cui purificazione potrebbe essere considerata, in futuro, per ottenere ulteriori prodotti di interesse commerciale. Il secondo progetto è stato indirizzato alla sintesi di potenziali inibitori dell’apertura del poro di transizione di permeabilità mitocondriale (mPTP), che è noto per essere responsabile dai danni da ischemia-riperfusione. Fino a questo momento, si conoscono solo pochi composti in grado di inibire questo complesso proteico. Tra questi sono presenti la dicicloesilcarbodiimmide (DCC) e l’oligomicina A le cui strutture sono state prese come punti di partenza per la costruzione dei nuovi inibitori. Poiché la DCC all’interno del corpo umano è lentamente idratata a dicicloesilurea (DCU), quest’ultima è stata selezionata come principale riferimento per la sintesi dei targets. Per questo motivo sono state sintetizzate differenti uree e tiouree simmetriche e asimmetriche. Inoltre sono stati sintetizzati due derivati carbammici per meglio comprendere l’importanza biologica di strutture cicliche adiacenti al gruppo carbonile. Per quanto riguarda la struttura dell’oligomicina A, si è optato per sintetizzare delle nuove molecole che possedessero uno spiro centro, come nel caso dell’oligomicina, ma che permettessero delle modifiche strutturali su più parti della molecola. In questo caso si è scelto l’1-fenil-1,3,8-triaza-spiro[4,5]decan-4-one, un composto commercialmente disponibile, per produrre i corrispettivi derivati sull’atomo di azoto in posizione 8. Quasi tutti i derivati sono stati sintetizzati con rese moderatamente alte, utilizzando reagenti economici e in condizioni di reazione blande. Inaspettatamente, i risultati preliminari provenienti da test biologici in vitro hanno mostrato che alcuni dei prodotti sintetizzati sembrano buoni inibitori, mentre altri sono risultati induttori dell’apertura dell’mPTP. Questi ultimi, nonostante non possano essere utilizzati nel campo del trattamento da IRI, potrebbero possedere un efficacia come composti anti-tumorali.
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Schäfer, Christian. "Reactivity of acetylenic ω-keto-esters towards transition metal complexes : synthesis of polycyclic motives of natural products." Thesis, Strasbourg, 2013. http://www.theses.fr/2013STRAF006/document.

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Les travaux décrits dans ce mémoire ont pour objet l’étude de la réactivité des ω-céto-esters acétyléniques vis-à-vis des métaux de transition. Lorsque ces composés sont traités avec une mélange Ti(OiPr)4/iPrMgBr, la formation d’alcools allyliques bicycliques est observée avec une totale diastéréosélectivité par rapport à la jonction de cycle (cis) et une configuration (E) pour la double liaison. Il a été montré que ces produits peuvent être transformés en lactone α,β-insaturé, sous-structures de produits naturels. La cycloisomérisation d’alcynyl cétones catalysées par des sels d’Ag(I) conduit à la formation de composés spiraniques. En piégeant l’intermédiaire réactionnel, la synthèse des composés vinyl-iodés correspondants a été réalisée. Si la réaction de cycloisomérisation est effectuée avec des ω-céto-esters acétyléniques, des ester α,β-insaturés sont isolés. Les produits obtenus ont ensuite été utilisés comme substrats pour la formation de systèmes tricycliques 6-5-5 et 6-6-5. Ces enchaînements de cycles sont présents dans le squelette carboné d’une grande variété de produits naturels. Les travaux décrits dans ce mémoire ont pour objet l’étude de la réactivité des ω-céto-esters acétyléniques vis-à-vis des métaux de transition. Lorsque ces composés sont traités avec une mélange Ti(OiPr)4/iPrMgBr, la formation d’alcools allyliques bicycliques est observée avec une totale diastéréosélectivité par rapport à la jonction de cycle (cis) et une configuration (E) pour la double liaison. Il a été montré que ces produits peuvent être transformés en lactone α,β-insaturé, sous-structures de produits naturels. La cycloisomérisation d’alcynyl cétones catalysées par des sels d’Ag(I) conduit à la formation de composés spiraniques. En piégeant l’intermédiaire réactionnel, la synthèse des composés vinyl-iodés correspondants a été réalisée. Si la réaction de cycloisomérisation est effectuée avec des ω-céto-esters acétyléniques, des ester α,β-insaturés sont isolés. Les produits obtenus ont ensuite été utilisés comme substrats pour la formation de systèmes tricycliques 6-5-5 et 6-6-5. Ces enchaînements de cycles sont présents dans le squelette carboné d’une grande variété de produits naturels
In this work, the reactivity of acetylenic ω-ketoesters towards different metal complexes was investigated. When acetylenic ω-ketoesters are submitted to Ti(OiPr)4/iPrMgBr, the formation of fused bicyclic γ-hydroxy-α,β-unsaturated esters was observed. The products were obtained with absolute selectivity in regard to the ring junction formed (cis) and the configuration of the double bond (E) and could be transformed into the corresponding α,β-unsaturated lactones, substructures of various natural products. When ω-ketoalkynes are used in Ag(I)-catalyzed cycloisomerization reactions, the formation of spirocyclic compounds was observed. By taking advantage of the reaction intermediates of this reaction, it was possible to isolate the corresponding spirocyclic alkenyl iodides. Performing cycloisomerization reactions with acetylenic ω-ketoesters, spirocyclic α,β-unsaturated esters are formed. We could show that these products are valuable substrates for the formation of 6-5-5- and 6-6-5-fused tricyclic systems which represent the skeleton of a large group of natural products
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Garcia, Fábio Dutra. "Novos Espirocromenil-Trifluoretanonas a partir de Reações de Trifluoracetilação de Adutos de Kabbe e seus Espiro[diidrocromeno-cicloalcan]pirazóis e Isoxazóis Derivados." Universidade Federal de Santa Maria, 2013. http://repositorio.ufsm.br/handle/1/10564.

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This work describes firstly an efficient and regioselective method for the synthesis of a new series of 2,2,2-trifluoro-1-[4-methoxy-spiro(2H-chromen-2,1 -cycloalkan)-3-yl]ethanones from the Kabbe adducts (spiro[chroman-2,1 -cycloalkan]-4-ones). Yields of 38 % to 61 % were obtained when trifluoroacetylation reactions of mixtures of enolethers and/or acetals derived from four spiro ketones (Kabbe adducts) were performed at a temperature of 45 oC and employing anhydrous chloroform as the solvent. Subsequently, when the respective trifluoroacetylated Kabbe adducts reacted with phenylhydrazine and methylhydrazine at a 1:1 molar ratio in refluxing ethanol for 24 hours, a new series of seven examples of a novel spiro-condensed heterocyclic system, namely 1(2)-methyl(phenyl)-3-(trifluoromethyl)-1,4(2,4)-dihydro-spiro(chromen[4,3-c]pyrazole-4,n -cycloalkanes) where cycloalkanes are cyclopentane, cyclohexane and cycloheptane (n = 1) and tetrahydro-2H-pyran (n = 2) were isolated at yields of between 35 % and 51 %. NMR and X-ray diffraction techniques demonstrated clearly that reactions from methylhydrazine and phenylhydrazine were regioselective and allowed to isolate separately the 1,3- and 2,3-trifluoromethylated isomers, respectively. Subsequently, two examples of new 3-hydroxy-3-(trifluoromethyl)-3,3a-dihydro-4H-spiro(chromen[4,3-c]isoxazole-4,1 -cycloalkanes), derivated from cyclopentanone and cyclopentanone, were obtained from the reaction of 2,2,2-trifluoro-1-[4-methoxy-spiro(2H-chromen-2,1 -cycloalkan)-3-yl]ethanones with hydroxylamine hydrochloride in yields of 42% and 58%, respectively. Finally, the structures of new spiro heterocycles were determined with the aid and simultaneous application of 1H-, 13C{1H}- and 19F-NMR, X-ray monocrystal diffraction, Mass Spectrometry and DFT calculation techniques and their purity were proved by elemental analysis or High Resolution Mass Spectrometry (HRMS).
O presente trabalho descreve inicialmente um método eficiente e regiosseletivo para a síntese de uma nova série de 2,2,2-triflúor-1-[4-metóxi-espiro(2H-cromen-2,1 -cicloalcan)-3-il]etanonas a partir de adutos de Kabbe (espiro[croman-2,1 -cicloalcan]-4-onas). Rendimentos de 38% a 61% foram obtidos quando reações de trifluoracetilação de misturas de enoléteres e/ou acetais derivados de quatro espiro cetonas (adutos de Kabbe) foram realizadas a 45 ºC usando clorofórmio anidro como solvente. Subsequentemente, quando os respectivos adutos de Kabbe trifluoracetilados foram reagidos com fenilhidrazina ou metilhidrazina, em relação molar de 1:1, sob refluxo de etanol por 24 horas, uma série de sete exemplares de um novo sistema heterocíclico espiro-condensado, denominado 1(2)-metil(fenil)-3-(trifluormetil)-1,4(2,4)-diidro-espiro(chromen[4,3-c]pirazol-4,n -cicloalcanos) onde os cicloalcanos são ciclopentano, ciclohexano e cicloheptano (n = 1) e tetraidro-2H-pirano (n = 2), foi isolada em rendimentos entre 35 % e 51 %. Técnicas de RMN e de difração de raios-X demonstraram claramente que as reações a partir da metilhidrazina e da fenilhidrazina foram regiosseletivas e permitiram isolar separadamente os isômeros trifluormetilados 1,3 e 2,3, respectivamente. Em sequência, dois exemplares de novas 3-hidróxi-3-(trifluormetil)-3,3a-diidro-4H-espiro(cromen[4,3-c]isoxazol-4,1 -cicloalcanos), derivados da ciclopentanona e ciclohexanona, foram obtidos a partir da reação de 2,2,2-triflúor-1-[4-metóxi-espiro(2H-cromen-2,1 -cicloalcan)-3-il]etanonas com cloridrato de hidroxilamina em rendimentos de 42% e 58%, respectivamente. Finalmente, as estruturas dos novos espiro heterociclos foram determinadas com o auxílio e aplicação simultânea de experimentos de RMN de 1H, 13C{1H}, 19F, difração de raios-X em monocristais, Espectrometria de Massas e cálculos DFT e, a sua pureza comprovada por Análise Elementar ou por Espectrometria de Massas de Alta Resolução (HRMS).
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Kern, Nicolas. "Réactivité d'azacycles en catalyse à l'or." Thesis, Strasbourg, 2014. http://www.theses.fr/2014STRAF012/document.

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La catalyse organométallique est l'un des piliers de la synthèse chimique moderne. Elle permet notamment la formation rapide de liaisons carbone-carbone et carbone-hétéroatome, processus les plus importants pour la fabrication des milliers de composés nécessaires à la vie contemporaine. Elle répond également aux critères d'économie d'atomes et d'énergie, et de réduction des déchets, des risques et des coûts de mise en oeuvre d'une réaction chimique.Parmi les thématiques les plus récentes de la synthèse organique, la catalyse homogène à l'or s'est imposée en seulement quelques années comme un outil synthétique très puissant. Elle autorise la génération rapide de complexité moléculaire à partir de substrats simples par l'activation d'insaturations carbonées. Durant ces études, nous avons tenté de tirer profit du caractère carbophile des complexes d'or (1) et (Ill) mais aussi de leur affinité pour certaines fonctions polaires pour transformer des hétérocycles acétyléniques en composés hétéropolycycliques dans des réactions en cascade. La réactivité complémentaire des complexes d'argent (1) a également été exploitée, ces derniers présentant de surcroît une sélectivité remarquable pour la déprotection d'éthers de méthoxybenzyle
Organometallic catalysis is a key tool of modern chemical synthesis. lts use is ubiquitous in the preparation of bulk or fine chemicals, in particular for the assembly of carbon-carbon and carbon-heteroatom bonds. Besides its overall efficiency, it responds to the responsible criteria of energy and atom economy, the reduction of waste, risk, and financial costs needed to perform a chemical reaction.ln just a few years, homogenous gold catalysis has emerged as an invaluable tool for the fast generation of molecular complexity. lndeed, it allows the strong electrophilic activation of unsaturated hydrocarbon moieties (e.g. alkynes or alienes). During this PhD thesis, we focused our studies on the use of gold's pi acidity as weil as its "classical" - but less discussed - Lewis acid character for the triggering of cascade reactions.Starting from acetylenic heterocycles, we targeted the synthesis of polycyclic compounds. The milder reactivity of silver complexes was also found useful in these reactions, as weil as in the deprotection of methoxybenzyl ethers
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PITZANTI, PATRIZIA. "Sintesi di molecole organiche enantiomericamente arricchite con l'uso della catalisi organica." Doctoral thesis, Università degli Studi di Cagliari, 2014. http://hdl.handle.net/11584/266431.

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The main topic of this thesis is the use of organocatalysis to synthesize organic compounds enantiomerically enriched. The first matter is about the synthesis of α-amino thioester derivatives through a tandem condensation-intramolecular rearrangement-protonation, this is a conceptually novel chiral Brønsted base/ Brønsted acid catalytic method that provides a number of important synthetic building blocks in good yields and with moderate and good enantioselectivities. The second topic is concerned to the synthesis of aldols derivatives of pyridine carbaldehydes functionalized in different positions using simple amino acids derivatives as catalysts, for example L-proline, L-pyrrolidine tetrazole and so on. This is important because is necessary to found news synthetic methods to produce pyridines nucleus that are very important building block for drugs. Following it is illustrated a preliminary result of a new methodological approach to the synthesis of enantiomerically enriched cyclopentanones starting from cyclobutanones and spirocyclopentanones, it is possible to expand the ring through an organocatalysed Michael reaction. This new approach takes advantages of the introduction of the α,β-unsatured aldehyde function on cyclobutanones. Finally, supramolecular interactions by halogen bonding are described. These occurs between enatiomerically enriched aldols benzothiophene derivatives, synthesized by means of organocatalysed reactions. These kinds of interactions are strongly important in supramolecular chemistry but also in biochemistry, materials and crystal engineering.
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Li, Qingyi. "Exploring a Symmetry Based Logic for Palau' Amine Synthesis." 2008. http://www4.utsouthwestern.edu/library/ETD/etdDetails.cfm?etdID=370.

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Books on the topic "Spiro compound"

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Torres, Ramon Rios, ed. Spiro Compounds. Wiley, 2022. http://dx.doi.org/10.1002/9781119567646.

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Torres, Ramon Rios. Spiro Compounds: Synthesis and Applications. Wiley & Sons, Limited, John, 2022.

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Torres, Ramon Rios. Spiro Compounds: Synthesis and Applications. Wiley & Sons, Incorporated, John, 2022.

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Torres, Ramon Rios. Spiro Compounds: Synthesis and Applications. Wiley & Sons, Incorporated, John, 2022.

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Torres, Ramon Rios. Spiro Compounds: Synthesis and Applications. Wiley & Sons, Incorporated, John, 2022.

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Deshayes, Kurt D. Studies of spiro[pyranindoline] compounds and their application to photodynamic transport. 1988.

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Book chapters on the topic "Spiro compound"

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Beckwith, A. L. J. "4.5.2.1 Radicals from fused rings and spiro compounds." In Inorganic Radicals, Metal Complexes and Nonconjugated Carbon Centered Radicals. Part 1, 568–71. Berlin, Heidelberg: Springer Berlin Heidelberg, 2007. http://dx.doi.org/10.1007/978-3-540-48466-0_108.

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Pudzich, R., T. Fuhrmann-Lieker, and J. Salbeck. "Spiro Compounds for Organic Electroluminescence and Related Applications." In Emissive Materials Nanomaterials, 83–142. Berlin, Heidelberg: Springer Berlin Heidelberg, 2006. http://dx.doi.org/10.1007/12_074.

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Coudret, C., A. V. Chernyshev, A. V. Metelitsa, and J. C. Micheau. "New Trends in Spiro-compounds Photochromic Metals Sensors: Quantitative Aspects." In Photon-Working Switches, 3–35. Tokyo: Springer Japan, 2017. http://dx.doi.org/10.1007/978-4-431-56544-4_1.

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Okada, Masahiko. "Ring-opening polymerization of bicyclic and spiro compounds. Reactivities and polymerization mechanisms." In Polymer Synthesis Oxidation Processes, 1–46. Berlin, Heidelberg: Springer Berlin Heidelberg, 1992. http://dx.doi.org/10.1007/3-540-55090-9_1.

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Itoh, T. "Of a Spiro Compound." In Monocyclic Arenes, Quasiarenes, and Annulenes, 1. Georg Thieme Verlag KG, 2010. http://dx.doi.org/10.1055/sos-sd-045-00644.

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Ninomiya, I., and T. Naito. "Spiro Compounds." In Photochemical Synthesis, 205–8. Elsevier, 1989. http://dx.doi.org/10.1016/b978-0-12-519490-7.50015-3.

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Itoh, T. "Of Spiro Compounds." In Monocyclic Arenes, Quasiarenes, and Annulenes, 1. Georg Thieme Verlag KG, 2010. http://dx.doi.org/10.1055/sos-sd-045-00655.

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Elk, Seymour B. "Spiro and related compounds." In A New Unifying Biparametric Nomenclature that Spans all of Chemistry, 206–57. Elsevier, 2005. http://dx.doi.org/10.1016/b978-044451685-5/50006-8.

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Williams, N. A. "Compounds containing a Spiro Phosphorus Atom." In Comprehensive Heterocyclic Chemistry III, 1065–126. Elsevier, 2008. http://dx.doi.org/10.1016/b978-008044992-0.01121-4.

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Drabowicz, Jozef, Rafal Karpowicz, Dorota Krasowska, Luca Sancineto, and Christian V. Stevens. "Compounds Containing a Spiro Phosphorus Atom." In Reference Module in Chemistry, Molecular Sciences and Chemical Engineering. Elsevier, 2020. http://dx.doi.org/10.1016/b978-0-12-818655-8.00016-0.

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Conference papers on the topic "Spiro compound"

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Cahyana, A. H., L. Alfiandri, and B. Ardiansah. "Synthesis of new spiro-naphthoquinone prepared from lawsone compound and test of antioxidant activity." In PROCEEDINGS OF THE 5TH INTERNATIONAL SYMPOSIUM ON CURRENT PROGRESS IN MATHEMATICS AND SCIENCES (ISCPMS2019). AIP Publishing, 2020. http://dx.doi.org/10.1063/5.0007882.

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Ichihashi, Kana, Masaki Okamura, Takuya Kanetomo, and Takayuki Ishida. "Synthetic investigation for spiro-junctioned biradical compounds." In THE IRAGO CONFERENCE 2018: A 360-degree Outlook on Critical Scientific and Technological Challenges for a Sustainable Society. Author(s), 2019. http://dx.doi.org/10.1063/1.5089444.

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Tamai, Naoto, and Hiroshi Masuhara. "Femtosecond Dynamics of C-O Bond Cleavage of a Spirooxazine Photochromic Reaction." In International Conference on Ultrafast Phenomena. Washington, D.C.: Optica Publishing Group, 1992. http://dx.doi.org/10.1364/up.1992.tuc19.

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Spirooxazines are known as typical organic compounds exhibiting photochromism [1]. Upon ultraviolet irradiation, the bond between the spiro carbon and oxygen undergoes fission, facilitating the structural change to form merocyanine as illustrated in scheme I.
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Spreitzer, Hubert, Horst Vestweber, Philipp Stoessel, and Heinrich Becker. "White and blue temperature stable and efficient OLEDs using amorphous spiro transport and spiro emitting compounds." In International Symposium on Optical Science and Technology, edited by Zakya H. Kafafi. SPIE, 2001. http://dx.doi.org/10.1117/12.416885.

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Choi, W. H., and S. K. So. "Charge injection and transport in spiro-linked arylamine compounds." In SPIE Photonic Devices + Applications, edited by Franky So and Chihaya Adachi. SPIE, 2009. http://dx.doi.org/10.1117/12.825555.

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Spreitzer, Hubert, Hermann W. Schenk, Josef Salbeck, Frank Weissoertel, Heike Reil, and Walter Riess. "Temperature stability of OLEDs using amorphous compounds with spiro-bifluorene core." In SPIE's International Symposium on Optical Science, Engineering, and Instrumentation, edited by Zakya H. Kafafi. SPIE, 1999. http://dx.doi.org/10.1117/12.372726.

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