Дисертації з теми "Tandem Cyclization"
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Rajinder, Kaur Maya. "Gold(I) Catalyzed Tandem Cyclization Reactions." Thesis, Norges teknisk-naturvitenskapelige universitet, Institutt for kjemi, 2012. http://urn.kb.se/resolve?urn=urn:nbn:no:ntnu:diva-19239.
Повний текст джерелаLam, Tin Yiu. "Synthesis of indoles via a tandem benzannulation-cyclization strategy." Thesis, Massachusetts Institute of Technology, 2008. http://hdl.handle.net/1721.1/46045.
Повний текст джерелаThesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2008.
Includes bibliographical references.
Vinylketenes (generated in situ from cyclobutenones or a-diazo ketones) react with ynamides via a pericyclic cascade process to produce highly-substituted aniline derivatives. Cyclization of the benzannulation products can then be achieved via several alternate procedures leading to indoles that are highly substituted on the six-membered ring. The cyclization approaches investigated as the second step in this tandem strategy included aromatic substitution, palladium-catalyzed oxidative amination, and nucleophilic cyclization. This thesis discusses the scope and limitations of this tandem strategy.
by Tin Yiu Lam.
Ph.D.
Mamaliga, Galina. "Progress towards the synthesis of tetracyclic heteroaromatic compounds via tandem benzannulation-cyclization strategies." Thesis, Massachusetts Institute of Technology, 2011. http://hdl.handle.net/1721.1/78512.
Повний текст джерелаCataloged from PDF version of thesis.
Includes bibliographical references.
A tandem benzannulation-cyclization strategy was successfully applied to the synthesis of a tetracyclic heteroaromatic compound expected to have interesting electronic properties. Benzannulation of a diazo ketone and a ynamide yielded a highly substituted aniline that was cyclized to indole according to protocols developed in our laboratory previously.
by Galina Mamaliga.
S.B.
Willumstad, Thomas P. (Thomas Paul). "Synthesis of highly substituted benzo-fused nitrogen heterocycles via tandem benzannulation/cyclization strategies." Thesis, Massachusetts Institute of Technology, 2013. http://hdl.handle.net/1721.1/84379.
Повний текст джерелаCataloged from PDF version of thesis.
Includes bibliographical references.
Benzannulations employing ynamides and vinylketenes (generated in situ from [alpha]-diazo ketones) were investigated. Irradiation of the diazo ketones using a batch or continuous-flow reactor leads to the formation of vinylketenes via a photo-Wolff rearrangement. The vinylketenes then react with ynamides via a pericyclic cascade process to produce highly substituted aniline derivatives. Using this vinylketene-based benzannulation, tandem strategies for the synthesis of highly substituted benzo-fused nitrogen heterocycles were investigated. A tandem benzannulation-iodocyclization method for the synthesis of polysubstituted quinolines was established. In addition, a tandem strategy for the synthesis of carbazoles was developed and applied in the total synthesis of the carbazole alkaloid carazostatin as well as formal syntheses of the alkaloids carbazoquinocin C and antiostatin A₄.
by Thomas P. Willumstad.
Ph.D.
Shah, Parin Ajay. "Synthesis of terpenoids using a tandem cationic cascade cyclization-electrophilic aromatic substitution reaction." Diss., University of Iowa, 2018. https://ir.uiowa.edu/etd/6639.
Повний текст джерелаKrismanich, Anthony. "Studies Related to Tandem Reactivity of 1-Carbomethoxy-5-dicyanomethyl-1,3-cyclohexadiene." Thesis, University of Waterloo, 2006. http://hdl.handle.net/10012/2954.
Повний текст джерелаThe ring-opened adduct was also envisaged as a potential substrate in intramolecular Heck reactions. To this end, Heck substrates were generated from the ring-opened adduct anion and iodo- and bromo-benzyl halides. A key observation at this stage pertained to the unexpected acidity of the ring-opened adduct C5 proton, which could be deprotonated by DBU to bring about allylic isomerization, a finding that would provide a key insight to the pattern of reactivity later evidenced with alkyl propiolates. Optimization of the Heck substrate-generating reaction was followed by Heck reactions under Jeffery's conditions, which generated angular tricycles as intended, accompanied by aromatic compounds generated by base-induced HCN elimination/rearrangement and dehydrogenation. The Jeffery's conditions were optimized to limit the production of aromatics.
The possibility of ring-opened adduct-derived vinyl silane intermediates undergoing cationic cyclizations led to a minor study based upon the bromination of allylsilanes and the elimination of TMSBr from 1,2-dibromo-3-trimethylsilyl compounds, accessible compounds unaccounted for in the review literature. It was determined that the combination of HBr and Br2 (perhaps as HBr3) was required to eliminate TMSBr, in contravention of the textbook account of electrophilic substitutions being the inherent reactions of allylsilanes and Br2.
Unexpected tandem reactivity was observed in the reactions of the anionic ring-opened adduct and alkyl propiolates under catalytic DBU conditions. Rather than tandem cyclization or simple adduct formation, the allenolate intermediates were determined to undergo extremely facile formal allenolate Cope rearrangements involving the ?,d-double-bond of the parent ring. Excess base intercepted the allenolate by deprotonating ring C5 and effecting 1,2-vinyl transfer by 3-exo-trig addition-elimination. The chemistry of the highly delocalized side-chain carbanion in the Cope product was studied in detail.
Yip, Kai-tai, and 葉啟泰. "Oxidative palladium catalysis under aerobic condition: studies on monocyclization of {221}-Keto amides and tandem cyclization ofAlkenyl anilines." Thesis, The University of Hong Kong (Pokfulam, Hong Kong), 2005. http://hub.hku.hk/bib/B34860605.
Повний текст джерелаXing, Dong, and 邢栋. "Transition metal-catalyzed C-N bond formation via addition of nitrogennucleophiles towards alkenes and related tandem cyclization reactions." Thesis, The University of Hong Kong (Pokfulam, Hong Kong), 2011. http://hub.hku.hk/bib/B46589156.
Повний текст джерелаSandoval, Sergio. "Tandem conjugate addition - cyclization reactors of L-methyl prolinate with [alpha,beta]-unsaturated ketones catalyzed by L-proline /." View online ; access limited to URI, 2008. http://0-digitalcommons.uri.edu.helin.uri.edu/dissertations/AAI3314459.
Повний текст джерелаYip, Kai-tai. "Oxidative palladium catalysis under aerobic condition : studies on monocyclization of [beta]-Keto amides and tandem cyclization of Alkenyl anilines /." Click to view the E-thesis via HKUTO, 2005. http://sunzi.lib.hku.hk/hkuto/record/B34860605.
Повний текст джерелаPatil, Dadasaheb V. "Intramolecular cyclization strategies for synthesizing medium-ring polycycles and the total synthesis of natural products." Diss., Georgia Institute of Technology, 2012. http://hdl.handle.net/1853/50118.
Повний текст джерелаSandelier, Matthew James. "Tandem reduction/cyclization of o-nitrophenyl propargyl alcohols--a novel synthesis of 2- & 2,4-disubstituted quinolines and application to the synthesis of streptonigrin." College Park, Md.: University of Maryland, 2008. http://hdl.handle.net/1903/8471.
Повний текст джерелаThesis research directed by: Dept. of Chemistry. Title from t.p. of PDF. Includes bibliographical references. Published by UMI Dissertation Services, Ann Arbor, Mich. Also available in paper.
Loertscher, Brad M. "Studies Toward the Synthesis of Lyconadin A and Cranomycin." BYU ScholarsArchive, 2013. https://scholarsarchive.byu.edu/etd/4243.
Повний текст джерелаMariaule, Gaëlle. "Accès original aux hétérocycles par la catalyse organométallique : développement de nouveaux inhibiteurs de kinases." Thesis, Paris 5, 2014. http://www.theses.fr/2014PA05P612/document.
Повний текст джерелаMy thesis proJect is organized around two main topics having in common organometallic chemistry and the synthesis of heterocycles.Firstly, we were interested in a methodology for the synthesis of tetrahydrocyclopenta[c]acridines. These compounds are synthesized in three steps from various quinolines. The key step is a cobalt-Catalyzed intramolecular Pauson-Khand reaction. Some compounds of this family exhibit selective Cyclin Dependent Kinases (CDKs) inhibition, particulary against CDK2, in the submicromolar range. A hit compound has been identified, and then using data from co-Crystallization with CDK2 and molecular modeling, followed by the study of structure-Activity relationships, the rational design of a second generation of molecules has been investigated. The most advanced compound has an IC50 of 300 nM against CDK2/cyclin A with an excellent metabolic profile. In the second axis of research, we have studied and developed a new silver-Catalyzed tandem addition/cyclization reaction with carbon nucleophiles. The systems studied are (hetero)aromatics compounds having an aldehyde group and in ortho-Position an alkynyl group. The synthetic strategy leads to 1H-Isochromene derivatives by creating two new bonds. A thorough study of the tandem reaction allowed us to obtain a wide range of isochromene derivatives, highlighting the influence of different substituents carried by the alkyne group or on the (hetero)aromatic substrates; and also to investigate the use of different carbon nucleophiles (alkynes, aromatics and heteroaromatics). The limitations of the tandem reaction have also been identified
Laio, Fang-Yu, and 廖芳瑜. "The Study of Free Radical Tandem Cyclization Reactions of Acylsilanes." Thesis, 2004. http://ndltd.ncl.edu.tw/handle/12163839257229825597.
Повний текст джерелаChang, Yi-Hsuan, and 張怡萱. "The Study of Tandem Radical Cyclization of Vinyl Radical with Acylsilanes." Thesis, 2007. http://ndltd.ncl.edu.tw/handle/63313572445229254747.
Повний текст джерелаHsu, Jen-Yu, and 徐仁佑. "The Study of Tandem Radical Cyclization of Vinyl Radical with Acylsilanes." Thesis, 2008. http://ndltd.ncl.edu.tw/handle/01886288224108411631.
Повний текст джерела國立臺灣大學
化學研究所
96
According to previous research in our laboratory, cyclizations of acylsilanes with vinyl radicals have been studied. This process involved intramolecular free radical cyclizations of a vinyl radical to the carbonyl group of acylsilane to give a β-silyl alkoxy radical. This radical then undergoes a radical Brook rearrangement to afford an α-silyloxy radical. Due to the presence of the vinyl group, this α-silyloxy radical is also an allylic radical. Finally, hydrogen abstraction occurs at the γ-position of this allylic system to give an enol silyl ether. Generally, 1,5-exo-cyclizations are more efficient than 1,6-exo-cyclizations. In this research we exploited this system further in the context of tandem radical cyclizations. We have constructed two systems in which the intermediate allylic radicals are trapped intramolecularly at the γ-position by radicalphilic groups. Specifically, we have synthesized acylsilanes with vinyl iodide tethered to an alkynyl functional group. The scope and limitations of this type of tandem cyclizations were studied.
Ordner, Ciara Mary. "Synthesis of Enantioenriched Heterocycles by Tandem Sakurai Allylation/Intramolecular Cyclization Processes." Thesis, 2018. https://thesis.library.caltech.edu/11238/1/CMO%20Senior%20Thesis%20-%20FINAL.pdf.
Повний текст джерелаHsu, Jen-Yu. "The Study of Tandem Radical Cyclization of Vinyl Radical with Acylsilanes." 2008. http://www.cetd.com.tw/ec/thesisdetail.aspx?etdun=U0001-2207200813360000.
Повний текст джерелаDhoro, Francis. "Part I, Interrupted Nazarov cyclization on silica gel: Part II, Tandem alkylation-cyclization process via an O,C dianion." Thesis, 2006. http://hdl.handle.net/10125/20467.
Повний текст джерелаKumar, Anil. "C-H Bond Functionalization and Tandem Cyclization with Alkynoates and Maleimides Using Directing Group Strategy." Thesis, 2022. https://etd.iisc.ac.in/handle/2005/5797.
Повний текст джерелаChen, Pei-Min, and 陳佩敏. "Tandem Cyclization of Enynes Containing an Ether Linkage and a Cyclopropyl Group via Ruthenium Metal Complex." Thesis, 2014. http://ndltd.ncl.edu.tw/handle/72759808192027849035.
Повний текст джерела國立臺灣大學
化學研究所
102
We study chemical reactions of [Ru]Cl ([Ru] = Cp(PPh3)2Ru) with three 1,8-enyne compounds containing cyclopropyl group (1, 7 and 11) in which the triple bond is associated with propargylic alcohol and the ole&;#64257;nic group has various substituted methyl groups. The reaction of [Ru]Cl and 1, containing one methyl group added to the internal carbon of the allyl group, affords the vinylidene complex 2 with a newly formed seven-membered ring. Furthermore, tandem cyclization reaction of 1 in MeOH/CHCl3 catalyzed by [Ru]NCCH3+PF6- at 60 oC leads to the product 6 with spiro-cyclopropyl ring, formed possibly via sequential allenylidene vinylidene cyclization followed by a nucleophilic addition of alkoxide. In CHCl3, the catalytic reaction by [Ru]NCCH3+ PF6- gives the isolable organic cyclization intermediate enyne 5. Treatment of the propargylic alcohol 7 containing two terminal methyl groups at the O-allylic group, with [Ru]Cl yields a mixture of two diastereomers of the vinylidene complex 8 containing a newly formed six-membered ring in a ratio of ca. 10:1. Among diastereoisomers only the anti-isomer is isolated for complex 8. The cyclization reaction is proposed to proceed via the formation of a six-membered ring boat-like transition state with bulkiest group in the pseudo-equatorial position to reduce the 1,3-diaxial interactions. The catalytic reaction by [Ru]NCCH3+PF6- in CHCl3 at 60 oC affords anti-9 and syn-9 in a ratio of 3:1. The thermal energy increases amount of product syn-9. The subsequent cyclization carried out in a cosolvent of ROH/CHCl3 at 60 oC affords bicyclic product 10. In the reaction of [Ru]Cl with 11, containing no methyl group, no C&;#8722;C bond formation is observed. The reaction of 11with [Ru]Cl in the presence of NH4PF6 in CH2Cl2 affords a mixture of the allenylidene complex 12 and phosphonium acetylide 13. Interestingly, thermal treatment of 11 leads to a ring expansion of the cyclopropyl group, giving the vinylidene complex 16 with a five-membered ring. This ring expansion proceeds by C-C bond formation between Cβ of the cumulative double bond and a methylene group of the cyclopropyl ring. Reaction of 1,3-diol 18 with [Ru]Cl in CH2Cl2 yields a mixture of the alkoxy carbene 17 and 19 in a ratio of 1:2. The spontaneous dehydration of 19 to 17 by elevating temperature is failed. Fortunately, complex 17 could be the only product when the reaction is carried out in MeOH. Overall, tandem cyclizations of two 1,8-enynes with methyl-substituents have been achieved. Ring-expansion of a cyclopropyl group in a 1,8-enyne with no methyl-substituent is also accomplished.
Nagaraju, CH. "Construction of Complex Polycyclic Systems using Gold Catalyzed Intramolecular Diyne/Enyne/ Hydroalkoxylation Reactions." Thesis, 2015. http://etd.iisc.ac.in/handle/2005/3840.
Повний текст джерелаNagaraju, CH. "Construction of Complex Polycyclic Systems using Gold Catalyzed Intramolecular Diyne/Enyne/ Hydroalkoxylation Reactions." Thesis, 2015. http://etd.iisc.ernet.in/2005/3840.
Повний текст джерелаMoon, David Thompson. "The Conjugate Addition of Novel Nucleophiles and Catalytic Intramolecular Tandem [1,5]-Hydride Shift / Cyclization and Friedel-Crafts Acylation with Alkylidene Meldrum’s Acid Derivatives." Thesis, 2008. http://hdl.handle.net/10012/4061.
Повний текст джерела"Part I, total synthesis of (±)-pallambins C and D: and, Part II, gold-catalyzed tandem cyclization towards substituted bicyclo[3.2.1]octenone derivatives : lead to total synthesis of dhilirolides A-D." 2013. http://library.cuhk.edu.hk/record=b5549785.
Повний текст джерела本文第一章首先概述pallavicinin 系的天然源,結構特點以及生物學效用。此外,重點介紹pallambins C 和D 的分,結構鑒定以及反合成分析。
第二章討消旋體pallambins C 和D 的全合成細節。該合成以消旋Wieland-Miescher ketone (WMK)為起始原,經38 步線性步驟得到最終產物。該合成線突出以下個重要的化學轉化:a) 一個由Grob 碎及分子內aldol成環反應組成的多米式程,構建目標分子內關鍵的二環[3.2.1]辛烷酮單元;b) 一個由脲/鈀體系催化的烷氧羰基化增環反應,構建稠環型四氫呋喃/γ 內酯雙環框架。
第三章總結本文的相關研究工作。
第四章給出相關工作的詳細實驗據。
Naturally occurring pallambins A-D isolated from the Chinese liverwort Pallavicinia ambigua are classified as modified labdane-type diterpenoids, many of which exhibit interesting biological activities. From a structural perspective, pallambins C and D are consisting of trienes and an unprecedented ladder-shaped [6-5-5-5] tetracyclic skeleton bearing seven contiguous stereogenic centers. Furthermore, the bridge of the bicyclo[3.2.1]octane segment is densely substituted with two methyl groups on the bridge-heads and a vinyl group on the carbon bridge. The skeletal novelty and potential bioactivities of pallambins C and D inspired us to explore their total synthesis. In this thesis, the first total synthesis of (±)-pallambins C and D is described.
In Chapter 1, a general introduction to the natural occurrence, structural features and biological potency of pallavicinin family is presented briefly. In addition, the background of pallambins C and D including isolation, structural elucidation and retrosynthetic analysis is emphasized.
In Chapter 2, detailed synthesis of (±)-pallambins C and D involving a linear 38 steps starting from the known (±)-Wieland-Miescher ketone is discussed. The synthetic approach features the following two key conversions: a) a domino process including Grob fragmentation and intramolecular aldol cyclization to build up the bicyclo[3.2.1]octanone embedded in the target molecules; b) a thiourea/palladium-catalyzed alkoxycarbonylative annulation to assemble the fused tetrahydrofuran/γ-lactone bicyclic framework.
Chaper 3 provides a conclusion of this research work.
Chapter 4 is concerned with the experimental details.
[With images.]
Detailed summary in vernacular field only.
Detailed summary in vernacular field only.
Detailed summary in vernacular field only.
Detailed summary in vernacular field only.
Detailed summary in vernacular field only.
Xu, Xuesong.
Thesis (Ph.D.)--Chinese University of Hong Kong, 2013.
Includes bibliographical references.
Abstracts also in Chinese.
ACKNOWLEDGEMENTS --- p.I
CONTENTS --- p.II
ABBREVIATIONS --- p.V
PART I:
ABSTRACT --- p.1
Chapter CHAPTER 1. --- INTRODUCTION
Chapter 1.1 --- General background --- p.4
Chapter 1.1.1 --- General introduction to liverworts --- p.4
Chapter 1.1.2 --- General introduction to terpenoids in liverworts --- p.5
Chapter 1.2 --- Introduction to pallavicinin family --- p.9
Chapter 1.2.1 --- Isolation and structural elucidation of pallavicinin compounds --- p.9
Chapter 1.2.2 --- Synthetic advances on pallavicinin family --- p.13
Chapter 1.3 --- Introduction to the present research --- p.16
Chapter 1.3.1 --- Structural elucidation and features of pallambins C and D --- p.16
Chapter 1.3.2 --- Biogenetic hypothesis and retrosynthetic analysis of pallambins C and D --- p..20
Chapter 1.4 --- Aim of the present work --- p.22
Chapter CHAPTER 2. --- RESULTS AND DISCUSSION --- p.24
Chapter 2.1 --- Previous synthetic effort on pallambin D (2) --- p.24
Chapter 2.2 --- Successful synthetic approach to 1 and 2 --- p.25
Chapter 2.2.1 --- Synthesis of compound 24 --- p.25
Chapter 2.2.2 --- Synthesis of compound 14 --- p.30
Chapter 2.2.3 --- Synthesis of compound 13 --- p.37
Chapter 2.2.4 --- Synthesis of compound 12 --- p.43
Chapter 2.2.5 --- Synthesis of 1 and 2 --- p.53
Chapter CHAPTER 3. --- CONCLUSION --- p.60
Chapter CHAPTER 4. --- EXPERIMENTAL SECTION --- p.62
REFERENCES --- p.104
PART II:
ABSTRACT --- p.110
Chapter CHAPTER 1. --- INTRODUCTION --- p.113
Chapter 1.1 --- Introduction to bicyclo[3.2.1]octane skeleton --- p.113
Chapter 1.1.1 --- Structural features of bicyclo[3.2.1]octane --- p.113
Chapter 1.1.2 --- Bicyclo[3.2.1]octane-containing bioactive natural products --- p.114
Chapter 1.1.3 --- Methodologies for synthesis of bicyclo[3.2.1]octane derivatives --- p.116
Chapter 1.1.4 --- Gold-catalyzed construction of bicyclo[3.2.1]octane unit --- p.117
Chapter 1.2 --- Background of the present research --- p.119
Chapter 1.2.1 --- Introduction to dhilirolides A-D --- p.119
Chapter 1.2.2 --- Retrosynthetic analysis of dhilirolide A (1) --- p.121
Chapter 1.3 --- Aim of the present work --- p.122
Chapter CHAPTER 2. --- RESULTS AND DISCUSSION --- p.124
Chapter 2.1 --- Synthesis of the key acetal allene precursor 6 --- p.124
Chapter 2.1.1 --- Preparation of the starting dimethoxyl ketone 7 --- p.124
Chapter 2.1.2 --- Preparation of alkynyl furan 11 --- p.126
Chapter 2.1.3 --- Preparation of acetal allene 6 --- p.128
Chapter 2.2 --- Synthesis of bicyclo[3.2.1]octenone derivative 5 --- p.134
Chapter 2.3 --- Synthesis of mono-tosylate 26 --- p.138
Chapter CHAPTER 3. --- CONCLUSION --- p.141
Chapter CHAPTER 4. --- EXPERIMENTAL SECTION --- p.143
REFERENCES --- p.162
APPENDIX --- p.167
Açıkalın, Serdar [Verfasser]. "Enantioselective synthesis of cyclic β-amino [beta amino] alcohols via tandem hydroalumination cyclization reduction of ethoxycarbonyl vinyl sulfoximines and application to the synthesis of potential aggrecanase inhibitors / vorgelegt von Serdar Açıkalın". 2009. http://d-nb.info/999784145/34.
Повний текст джерела"Synthesis of nordihydroguaiaretic acid (NDGA) analogues and their oxidative metabolism." Thesis, 2015. http://hdl.handle.net/10388/ETD-2015-06-1915.
Повний текст джерелаLin, Chi-Feng, and 林其鋒. "The Study of Tandem Free Radical Cyclizations of Acylsilanes Involving Alkyne as Terminator." Thesis, 2002. http://ndltd.ncl.edu.tw/handle/55165756602313426084.
Повний текст джерелаChang, Ching-Jung, та 張慶榮. "Tandem Radical Cyclizations initiated by α-Carbonyl Radicals: (1) Total synthesis of (+)-Paniculatine .(2) Synthetic studies for Total Synthesis of Ingenol". Thesis, 1998. http://ndltd.ncl.edu.tw/handle/85392832879732180827.
Повний текст джерела