Relevant bibliographies by topics / Donor-Acceptor cyclopropane

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  2. Dissertations / Theses
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Academic literature on the topic 'Donor-Acceptor cyclopropane'

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Published: 25 May 2024

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Journal articles on the topic "Donor-Acceptor cyclopropane"

1

Craig, Alexander J., and Bill C. Hawkins. "The Bonding and Reactivity of α-Carbonyl Cyclopropanes." Synthesis 52, no. 01 (October 1, 2019): 27–39. http://dx.doi.org/10.1055/s-0039-1690695.

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The cyclopropane functionality has been exploited in a myriad of settings that range from total synthesis and methodological chemistry, to medical and materials science. While it has been seen in such a breadth of settings, the typical view of the cyclopropane moiety is that its reactivity is derived primarily from the release of ring strain. While this simplified view is a useful shorthand, it ignores the specific nature of cyclopropyl molecular orbitals. This review aims to present the different facets of cyclopropane bonding by examining the main models that have been used to explain the reactivity of the functionality over the years. However, even with advanced theory, being able to precisely predict the reactivity of an exact system is nigh impossible. Specifically chosen, carbonyl-bearing cyclopropyl species act as so-called acceptor cyclopropanes and, if correctly derivatised, donor–acceptor cyclopropanes. By undertaking a case study of the history of carbonyl cyclopropanes in organic synthesis, this review highlights the relationship between the understanding of theory and pattern recognition in developing new synthetic methods and showcases those successful in balancing this critical junction.1 Cyclopropanes2 The Strain Model3 The Forster–Coulsin–Moffit Model4 The Walsh Model5 Acceptor, Donor, and Donor–Acceptor Cyclopropanes6 Reactions of Carbonyl Cyclopropanes
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Boichenko, Maksim A., Andrey Yu Plodukhin, Vitaly V. Shorokhov, Danyla S. Lebedev, Anastasya V. Filippova, Sergey S. Zhokhov, Elena A. Tarasenko, Victor B. Rybakov, Igor V. Trushkov, and Olga A. Ivanova. "Synthesis of 1,5-Substituted Pyrrolidin-2-ones from Donor–Acceptor Cyclopropanes and Anilines/Benzylamines." Molecules 27, no. 23 (December 2, 2022): 8468. http://dx.doi.org/10.3390/molecules27238468.

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We developed a straightforward synthetic route to pharmacologically important 1,5-substituted pyrrolidin-2-ones from donor–acceptor cyclopropanes bearing an ester group as one of the acceptor substituents. This method includes a Lewis acid-catalyzed opening of the donor–acceptor cyclopropane with primary amines (anilines, benzylamines, etc.) to γ-amino esters, followed by in situ lactamization and dealkoxycarbonylation. The reaction has a broad scope of applicability; a variety of substituted anilines, benzylamines, and other primary amines as well as a wide range of donor–acceptor cyclopropanes bearing (hetero)aromatic or alkenyl donor groups and various acceptor substituents can be involved in this transformation. In this process, donor–acceptor cyclopropanes react as 1,4-C,C-dielectrophiles, and amines react as 1,1-dinucleophiles. The resulting di- and trisubstituted pyrrolidin-2-ones can be also used in subsequent chemistry to obtain various nitrogen-containing polycyclic compounds of interest to medicinal chemistry and pharmacology, such as benz[g]indolizidine derivatives.
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3

Mead, Keith, and Yahaira Reyes. "Acetoxy-Substituted Cyclopropane Dicarbonyls as Stable Donor–Acceptor–Acceptor Cyclopropanes." Synthesis 47, no. 19 (June 25, 2015): 3020–26. http://dx.doi.org/10.1055/s-0034-1379934.

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4

Fadeev, Alexander A., Alexey O. Chagarovskiy, Anton S. Makarov, Irina I. Levina, Olga A. Ivanova, Maxim G. Uchuskin, and Igor V. Trushkov. "Synthesis of (Het)aryl 2-(2-hydroxyaryl)cyclopropyl Ketones." Molecules 25, no. 23 (December 5, 2020): 5748. http://dx.doi.org/10.3390/molecules25235748.

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A simple general method for the synthesis of 1-acyl-2-(ortho-hydroxyaryl)cyclopropanes, which belong to the donor–acceptor cyclopropane family, has been developed. This method, based on the Corey–Chaykovsky cyclopropanation of 2-hydroxychalcones, allows for the preparation of a large diversity of hydroxy-substituted cyclopropanes, which can serve as promising building blocks for the synthesis of various bioactive compounds.
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Grover, Huck K., Michael R. Emmett, and Michael A. Kerr. "Carbocycles from donor–acceptor cyclopropanes." Organic & Biomolecular Chemistry 13, no. 3 (2015): 655–71. http://dx.doi.org/10.1039/c4ob02117g.

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Reyes, Yahaira, and Keith T. Mead. "ChemInform Abstract: Acetoxy-Substituted Cyclopropane Dicarbonyls as Stable Donor-Acceptor-Acceptor Cyclopropanes." ChemInform 47, no. 7 (January 2016): no. http://dx.doi.org/10.1002/chin.201607087.

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7

Budynina, Ekaterina, Konstantin Ivanov, Ivan Sorokin, and Mikhail Melnikov. "Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleo­philes." Synthesis 49, no. 14 (May 18, 2017): 3035–68. http://dx.doi.org/10.1055/s-0036-1589021.

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Ring opening of donor–acceptor cyclopropanes with various N-nucleophiles provides a simple approach to 1,3-functionalized compounds that are useful building blocks in organic synthesis, especially in assembling various N-heterocycles, including natural products. In this review, ring-opening reactions of donor–acceptor cyclopropanes with amines, amides, hydrazines, N-heterocycles, nitriles, and the azide ion are summarized.1 Introduction2 Ring Opening with Amines3 Ring Opening with Amines Accompanied by Secondary Processes Involving the N-Center3.1 Reactions of Cyclopropane-1,1-diesters with Primary and Secondary Amines3.1.1 Synthesis of γ-Lactams3.1.2 Synthesis of Pyrroloisoxazolidines and -pyrazolidines3.1.3 Synthesis of Piperidines3.1.4 Synthesis of Azetidine and Quinoline Derivatives3.2 Reactions of Ketocyclopropanes with Primary Amines: Synthesis of Pyrrole Derivatives3.3 Reactions of Сyclopropane-1,1-dicarbonitriles with Primary Amines: Synthesis of Pyrrole Derivatives4 Ring Opening with Tertiary Aliphatic Amines5 Ring Opening with Amides6 Ring Opening with Hydrazines7 Ring Opening with N-Heteroaromatic Compounds7.1 Ring Opening with Pyridines7.2 Ring Opening with Indoles7.3 Ring Opening with Di- and Triazoles7.4 Ring Opening with Pyrimidines8 Ring Opening with Nitriles (Ritter Reaction)9 Ring Opening with the Azide Ion10 Summary
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Ivanova, Olga, Vladimir Andronov, Irina Levina, Alexey Chagarovskiy, Leonid Voskressensky, and Igor Trushkov. "Convenient Synthesis of Functionalized Cyclopropa[c]coumarin-1a-carboxylates." Molecules 24, no. 1 (December 24, 2018): 57. http://dx.doi.org/10.3390/molecules24010057.

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A simple method has been developed for the synthesis of cyclopropa[c]coumarins, which belong to the donor-acceptor cyclopropane family and, therefore, are promising substrates for the preparation of chromene-based fine chemicals. The method, based on the acetic acid-induced intramolecular transesterification of 2-arylcyclopropane-1,1-dicarboxylates, was found to be efficient for substrates containing hydroxy group directly attached to the aromatic ring.
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Liu, Haidong, Lifang Tian, Hui Wang, Zhi-Qiang Li, Chi Zhang, Fei Xue, and Chao Feng. "A novel type of donor–acceptor cyclopropane with fluorine as the donor: (3 + 2)-cycloadditions with carbonyls." Chemical Science 13, no. 9 (2022): 2686–91. http://dx.doi.org/10.1039/d2sc00302c.

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A new type of donor–acceptor cyclopropane with gem-difluorine as an unconventional donor group undergoes (3 + 2)-cycloadditions with various aldehydes/ketones, affording densely functionalized gem-difluorotetrahydrofurans.
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10

Cavitt, Marchello A., Lien H. Phun, and Stefan France. "Intramolecular donor–acceptor cyclopropane ring-opening cyclizations." Chem. Soc. Rev. 43, no. 3 (2014): 804–18. http://dx.doi.org/10.1039/c3cs60238a.

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Dissertations / Theses on the topic "Donor-Acceptor cyclopropane"

1

Cavitt, Marchello Alfonzo. "Stress relief: Exercising Lewis acid catalysis for donor-acceptor cyclopropane ring-opening annulations, a basis for new reaction methodologies." Diss., Georgia Institute of Technology, 2015. http://hdl.handle.net/1853/54448.

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Nature’s biodiversity is complex and filled with beauty and wonder which are all observable on the macroscopic scale. This exquisiteness of nature’s intricacies are mirrored on the molecular level such that substances, large or small, are assembled to serve as signaling molecules, protective agents, and fundamental composites of higher-order frameworks for the operation and survival of life. Over the years, chemists have isolated and synthesized these molecules, known as natural products, to understand and evaluate their functions in biology and potential for medicinal applications. Although bioactive natural products demonstrate medicinal promise, poor pharmacological effects require further derivatization because semisynthesis is not sufficient to refine adverse pharmacokinetics. For some active molecules, isolation results in poor yields. In addition to small quantity isolation, many natural products, reflecting the immense complexity of biology itself, pose difficult synthetic challenges to organic chemists because of skeletal heterogeneity, stereochemical complexity, and substitution divergence. As a result of these synthetic obstacles to natural product utilization, improvements are needed in current chemical approaches, and new innovative methodologies for synthesis and chemical space exploration are necessary. Pharmaceutically relevant frameworks, natural products, and synthetic biologically active molecules are comprised of polycarbocyclic and heterocyclic scaffolds. Traditionally, cycloadditions, transannular transformations, and annulation reactions serve as powerful methods for polycyclic formation. In order to assemble diverse polycycles, donor-acceptor cyclopropanes are useful, versatile synthetic equivalents for C-C bond formations. By taking advantage of the strain within these unique, polarized systems, differing molecular architectures can be accessed directly to perform contemporary organic synthesis. Moreover, the donor-acceptor cyclopropanes initially utilized in these studies provided a fundamental basis for new methods to synthesize other relevant scaffolds. Unique, efficient, Lewis acid-catalyzed intramolecular cyclization strategies for the construction of functionalized polycycles using Friedel-Crafts-type alkylation sequences are presented to expand the reaction repertoire of the molecular architect. Generally, products were formed from commercially-available starting materials in high yields with broad scope. The methodologies were demonstrated to be modular, operationally simple, and amenable to different substitution patterns and functional groups to afford tetrahydroindolizines, heteroaromatic cyclohexenones, hydropyrido[1,2-a]indoles, pyrrolo[1,2-a]indoles, pyrrolo[3,2,1-ij]quinolines, pyrrolizines, and tetrahydrobenzo[ij]quinolizines. To demonstrate the utility of the methodologies devised, progress toward, (±)-rhazinicine, a natural product, is discussed. This dissertation is organized into six chapters: (1) an introduction, paradoxical stress and molecular strain’s utility in synthesis; (2) annulation reactions for the formation of heteroaromatic cyclohexenones; (3) hydropyrido[1,2-a]indole formation via an In(III)-catalyzed cyclopropane ring-opening/Friedel-Crafts alkylation sequence; (4) tetrahydroindolizine formation and progress toward the total synthesis of (±)-rhazinicine (5) pyrrolo[1,2-a]indole synthesis using a Michael-type Friedel-Crafts cyclization approach; and (6) a versatile protocol for the intramolecular formation of functionalized pyrrolo[3,2,1-ij]quinolines.
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2

Colonna, Pierre. "Un cyclopropane donneur-accepteur original pour la synthèse de benzocylobutènes substitués via une cascade réactionnelle." Electronic Thesis or Diss., Aix-Marseille, 2022. http://www.theses.fr/2022AIXM0336.

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Les dérivés BenzoCycloButènes (BCBs) constituent une classe unique de molécules correspondant au greffage d’un cycle carboné à 4 chaînons sur un motif aromatique. L’effet coopératif entre la stabilité thermodynamique du noyau aromatique d’une part et la grande réactivité du cycle tendu d’autre part en font une brique moléculaire original ayant diverses applications telle que le développement de polymères. En parallèle, les cyclopropanes sont des molécules hautement valorisables car il s’agit d’éléments permettant d’atteindre une grande complexité moléculaire dans une démarche à économie d’atome et souvent par le biais de réactions originales initiées par la relâche de tension de cycle. Dans ce contexte, une nouvelle classe de cyclopropane donneur-accepteur (CDA) a récemment été développé au sein de notre laboratoire et fait appel d’une part à un motif cyclopropanol protégé par un éther sylilé (donneur) et d’autre part à un ester α,β-insaturé (accepteur). Ce composé peut aisément être valorisé pour conduire avec de bons rendements au Benzocyclobutènes (BCB) hautement fonctionnalisés correspondant. Les expériences menées au sein de notre laboratoire ont démontré qu’en fonction de la substitution de la partie donatrice du CDA, une approche en une ou deux étapes devait être adopté. De cette manière, une librairie de BCB substitués par des groupements aussi bien alkyles qu’aryles a été mise au point. Nos études mécanistiques ont permis de démontrer expérimentalement que la régiosélectivité observée sur le BCB substitué est totalement dépendante de la diastéréochimie du précurseur CDA
Benzocyclobutenes (BCBs) derivatives are of significant interest due to the cooperative effects between the thermodynamic stability coming from the aromatic ring and the high reactivity of the strained cyclobutene moiety. In this regard, BCBs have been used as an original building block for the synthesis of natural products and also as precursors for the development of polymers. On the other hand, small rings represent a valuable three-atoms building element in the search to reach molecular complexity in an atom economical manner and often participate in fascinating chemical transformations. This release of ring tension usually allows for a scalable, rapid and controlled synthetic access to the expected target molecules. In this context, a new class of donor-acceptor cyclopropane (DAC) has recently been developed in our laboratory combining a silyl protected cyclopropanol with an α,β-unsaturated ester. Gratifyingly, the latter delivered the corresponding highly functionalized benzocyclobutenes in good yields. Experimental investigations demonstrated that depending on the substitutions of the silyl protected cyclopropanol (donor part), a one-step or two-steps approach had to be adopted. In this way, a library of BCB with alkyl- or aryl- substituent on the cyclobutene ring have been synthesised. Mechanistic studies demonstrated experimentally the total regioselectivity observed on the substituted BCB depending on the diastereochemistry of the DAC. Finally, the synthesis of taylor-made monomers has been also explored. Typically, the introduction of an alkoxy or amino group on the four-membered ring has been envisaged thanks to a post-functionalisation approach
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3

Sanders, Shanina Devondia Brookhart Maurice S. "Lewis acid-catalyzed cycloaddition reactions of donor-acceptor cyclopropanes." Chapel Hill, N.C. : University of North Carolina at Chapel Hill, 2009. http://dc.lib.unc.edu/u?/etd,2534.

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Thesis (Ph. D.)--University of North Carolina at Chapel Hill, 2009.
Title from electronic title page (viewed Oct. 5, 2009). "... in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the Department of Chemistry." Discipline: Chemistry; Department/School: Chemistry.
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4

Lund, Elizabeth Anne. "Studies of samarium(II) iodide-induced ring openings and donor-acceptor cyclopropanes." Thesis, University of Ottawa (Canada), 1994. http://hdl.handle.net/10393/6817.

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Studies based on radical-induced ring openings of halolactones, spirocyclobutanones, and Rh$\sb2$(OAc)$\sb4$-catalyzed reactions of $\alpha$-diazoketones are described. Novel ring openings and subsequent decarboxylations of iodolactone 66 and bromolactone 67 to give diene 78 were found to proceed under SmI$\sb2$/THF/HMPA (4 equiv) conditions. Upon treatment of iodothialactone 63, iodolactone 66 or bromolactone 67 with SmI$\sb2$/THF/HMPA with "reverse addition" it was found that the ring-opened unsaturated acid 79 was obtained in good yield in each case. The unprecedented ring opening reactions of $\alpha$-ketospirocyclobutanes 123 and 124 with SmI$\sb2$ afforded ketones 126 and 127 in 70% and 88% yield, respectively. Dihydrofurans 217 and 224 were prepared from azibenzil (210) and $\alpha$-diazoketone 223, respectively, via Rh$\sb2$(OAc)$\sb4$-catalyzed reactions with ethyl vinyl ether. The structures of 217 and 224 were rigorously established and the former assignments were corrected. These structures (217 and 224) were unamiguously assigned by characterization of the corresponding transketalization products 222 and 226. Preliminary studies towards the preparation of the novel hydrocarbon-soluble Sm(II) complex 88 are presented. An unprecedented Grob-type fragmentation is postulated to explain the formation of benzyl alcohol from the DIBAL reduction of the donor-acceptor cyclopropane 215. Cyclopropyl alcohol 259 was also produced from this reaction. The characterization of 259 established the intermediacy of donor-acceptor cyclopropanes in the production of dihydrofurans 217 and 224, and suggests that this pathway is more general than the literature implies.$\sp*$ ftn$\sp*$Please refer to the dissertation for diagrams.
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Dousset, Maxime. "Réaction d'expansion de cycle : études dirigées vers l'accès aux cycles de taille moyenne via des espèces polarisées." Thesis, Aix-Marseille, 2017. http://www.theses.fr/2017AIXM0577.

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Pour la recherche de candidats d’intérêt thérapeutique, l’accès à des systèmes carbonés toujours plus complexes peut se heurter à divers problèmes synthétiques. Afin d’enrichir la diversité structurales, il est nécessaire de pallier aux difficultés synthétiques par le développement de nouveaux outils de synthèse. Dans ce contexte, ce travail s’est principalement orienté sur l’accès de cycles carbonés par des réactions d’expansion de cycle via l’utilisation de composés polarisés. Une première partie est réalisée avec l’utilisation de l’α-chlorodiazoacétate d’éthyle dans la réaction d’expansion de cycle de Tiffeneau-Demjanov pour la synthèse de céto-esters cycliques avec l’incorporation d’un centre tétrasubstitué présentant un atome de chlore. Dans un second temps, le développement d’une réaction de cycloaddition (5+3) à partir de deux entités cyclopropaniques polarisées a été mené au laboratoire. Cette méthodologie a conduit à décrire une nouvelle réactivité des composés cyclopropanes donneurs-accepteurs pour former des lactones α,β,γ-trisubstituées via une activation avec un acide de BrØnsted. Une étude approfondie par des calculs théoriques ont permis d’appréhender le mécanisme réactionnel et la sélectivité de cette transformation. La dernière partie a examinée la réactivité d’une nouvelle classe de molécule : les vinylbiscyclopropanes. Ces composés peuvent conduire à la famille des benzocyclobutènes et aux composés cycliques à 8 chainons par des réactions de réarrangement ou de transposition sigmatropique [3.3] formelle. Ce dernier motif est toujours à l’étude et devrait permettre un accès rapide à de multiples structures carbonées
In the quest for new therapeutic candidates, the description of novel synthetic approaches to access to increasingly complex carbon systems remains a daunting challenge. In order to increase the structural of such scaffolds, it is necessary to overcome the encountered difficulties by developing new straightforward an efficient tools. In this context, this work has mainly focused on the access of structurally defined carbon cycles by ring expansion reactions via the use of polarized compounds. The first part of this study has been devoted to the Tiffeneau-Demjanov ring expansion reaction using ethyl α-chlorodiazoacetate. This approach allowed us to access highly versatile cyclic keto esters displaying a tetrasubstitued carbon center bearing a chlorine atom. The next topic of this study has been focused on the development of a (5 + 3) cycloaddition reaction between two polarized cyclopropane entities. This methodology led to the description of a novel reactivity of donor-acceptor cyclopropanes compounds to form α,β,γ-trisubstituted lactones under a BrØnsted acid activation. In order to gain mechanistic insights, a theoretical study has also been conducted which led us to rationalize the mechanism and the selectivity of this transformation. The last part described the reactivity of a underexplored class of molecule, the vinylbiscyclopropanes. These compound, can lead to the benzocyclobutene family and to the 8 membered-ring compounds through rearrangement or formal [3.3] sigmatropic rearrangement reaction. This last class of compound is still under study and should allow rapid access to diverse cyclic structures
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6

Gladow, Daniel [Verfasser]. "Darstellung von perfluoralkyl- und perfluoraryl-substituierten Heterocyclen ausgehend von Donor-Acceptor-Cyclopropanen / Daniel Gladow." Berlin : Freie Universität Berlin, 2014. http://d-nb.info/1052893945/34.

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7

Dousset, Maxime. "Réaction d'expansion de cycle : études dirigées vers l'accès aux cycles de taille moyenne via des espèces polarisées." Electronic Thesis or Diss., Aix-Marseille, 2017. http://www.theses.fr/2017AIXM0577.

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Pour la recherche de candidats d’intérêt thérapeutique, l’accès à des systèmes carbonés toujours plus complexes peut se heurter à divers problèmes synthétiques. Afin d’enrichir la diversité structurales, il est nécessaire de pallier aux difficultés synthétiques par le développement de nouveaux outils de synthèse. Dans ce contexte, ce travail s’est principalement orienté sur l’accès de cycles carbonés par des réactions d’expansion de cycle via l’utilisation de composés polarisés. Une première partie est réalisée avec l’utilisation de l’α-chlorodiazoacétate d’éthyle dans la réaction d’expansion de cycle de Tiffeneau-Demjanov pour la synthèse de céto-esters cycliques avec l’incorporation d’un centre tétrasubstitué présentant un atome de chlore. Dans un second temps, le développement d’une réaction de cycloaddition (5+3) à partir de deux entités cyclopropaniques polarisées a été mené au laboratoire. Cette méthodologie a conduit à décrire une nouvelle réactivité des composés cyclopropanes donneurs-accepteurs pour former des lactones α,β,γ-trisubstituées via une activation avec un acide de BrØnsted. Une étude approfondie par des calculs théoriques ont permis d’appréhender le mécanisme réactionnel et la sélectivité de cette transformation. La dernière partie a examinée la réactivité d’une nouvelle classe de molécule : les vinylbiscyclopropanes. Ces composés peuvent conduire à la famille des benzocyclobutènes et aux composés cycliques à 8 chainons par des réactions de réarrangement ou de transposition sigmatropique [3.3] formelle. Ce dernier motif est toujours à l’étude et devrait permettre un accès rapide à de multiples structures carbonées
In the quest for new therapeutic candidates, the description of novel synthetic approaches to access to increasingly complex carbon systems remains a daunting challenge. In order to increase the structural of such scaffolds, it is necessary to overcome the encountered difficulties by developing new straightforward an efficient tools. In this context, this work has mainly focused on the access of structurally defined carbon cycles by ring expansion reactions via the use of polarized compounds. The first part of this study has been devoted to the Tiffeneau-Demjanov ring expansion reaction using ethyl α-chlorodiazoacetate. This approach allowed us to access highly versatile cyclic keto esters displaying a tetrasubstitued carbon center bearing a chlorine atom. The next topic of this study has been focused on the development of a (5 + 3) cycloaddition reaction between two polarized cyclopropane entities. This methodology led to the description of a novel reactivity of donor-acceptor cyclopropanes compounds to form α,β,γ-trisubstituted lactones under a BrØnsted acid activation. In order to gain mechanistic insights, a theoretical study has also been conducted which led us to rationalize the mechanism and the selectivity of this transformation. The last part described the reactivity of a underexplored class of molecule, the vinylbiscyclopropanes. These compound, can lead to the benzocyclobutene family and to the 8 membered-ring compounds through rearrangement or formal [3.3] sigmatropic rearrangement reaction. This last class of compound is still under study and should allow rapid access to diverse cyclic structures
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8

Patil, 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.

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Carbo- and heterocyclic compounds are of great interest to chemists. Intramolecular cyclization strategies of donor-acceptor (D-A) cyclopropanes and alkylidene malonate monoamides have excellent potential for synthesis as they offer easy access to structurally-diverse compounds. The work described in this thesis accesses the scope of the In(OTf)3-catalyzed cyclization reaction of cyclopropanes and alkylidene malonate monoamides. In(OTf)3-catalyzed reactions of alkenyl and heteroaryl cyclopropyl ketones were examined in the synthesis of functionalized cyclohexenone-based derivatives (Chapter 2). Subsequent efforts to utilize a tandem cyclopropane ring-opening/Friedel-Crafts alkylation sequence of methyl 1-(1H-indolecarbonyl)-1-cyclopropanecarboxylates to prepare functionalized hydropyrido[1,2-a]indole-6(7H)-ones is discussed in Chapter 3. The extension of this tandem protocol towards the total synthesis of (±)-deethyleburnamonine is the subject of Chapter 6. Intramolecular Friedel-Crafts alkylation of N-indolyl alkylidene malonate monoamides was also examined. An In(OTf)3-catalyzed cyclization of substituted methyl 2-(1H-indole-1-carbonyl) acrylates afforded a series of 1H-pyrrolo[1,2-a]indole-3(2H)-ones (Chapter 4), whereas substrates with the indole 2-position blocked provided access to substituted 4H-pyrrolo[3,2,1-ij]quinolin-4-ones (Chapter 5).
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Yu, Ming. "New chemistry of donor-acceptor cyclopropanes." Thesis, 2004. http://hdl.handle.net/2152/1441.

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Yu, Ming Pagenkopf Brian L. "New chemistry of donor-acceptor cyclopropanes." 2004. http://repositories.lib.utexas.edu/bitstream/handle/2152/1441/yum73355.pdf.

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Books on the topic "Donor-Acceptor cyclopropane"

1

Banerjee, Prabal, and Akkattu T. Biju. Donor-Acceptor Cyclopropanes in Organic Synthesis. Wiley & Sons, Incorporated, John, 2022.

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Banerjee, Prabal, and Akkattu T. Biju. Donor-Acceptor Cyclopropanes in Organic Synthesis. Wiley & Sons, Limited, John, 2022.

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Banerjee, Prabal, and Akkattu T. Biju. Donor-Acceptor Cyclopropanes in Organic Synthesis. Wiley & Sons, Incorporated, John, 2022.

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Banerjee, Prabal, and Akkattu T. Biju. Donor-Acceptor Cyclopropanes in Organic Synthesis. Wiley & Sons, Incorporated, John, 2022.

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Novikov, Roman, Denis Borisov, Leonid Menchikov, and Yuriy Tomilov. Donor-acceptor cyclopropanes. Cycloaddition and annulation reactions. LCC MAKS Press, 2022. http://dx.doi.org/10.29003/m2659.978-5-317-06797-7.

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This is the second book in the Donor-Acceptor Cyclopropanes series. It summarizes and analyzes for the first time the main intermediates formed from D-A cyclopropanes, and also systematizes the main ways of their further transformations. The main attention is paid to the cycloaddition and annulation reactions of D-A cyclopropanes with various substrates under the action of Lewis acids, which are of the greatest practical importance in organic synthesis. The monograph is addressed to a wide range of specialists in the field of small cycle chemistry and organic synthesis, including the synthesis of natural compounds and biologically active substances
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Book chapters on the topic "Donor-Acceptor cyclopropane"

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Reißig, H. U. "Donor-Acceptor-Substituted Cyclopropanes via Fischer Carbene Complexes." In Organometallics in Organic Synthesis 2, 311–22. Berlin, Heidelberg: Springer Berlin Heidelberg, 1989. http://dx.doi.org/10.1007/978-3-642-74269-9_17.

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Wienand, A., M. Buchert, B. Hofmann, and H. U. Reissig. "The Carbene Complex Route to Donor-Acceptor-Substituted Cyclopropanes." In Advances in Metal Carbene Chemistry, 271–73. Dordrecht: Springer Netherlands, 1989. http://dx.doi.org/10.1007/978-94-009-2317-1_30.

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Reißig, Hans-Ulrich. "Donor-acceptor-substituted cyclopropanes: Versatile building blocks in organic synthesis." In Topics in Current Chemistry, 73–135. Berlin, Heidelberg: Springer Berlin Heidelberg, 1988. http://dx.doi.org/10.1007/bfb0111229.

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Lambert, Tristan H. "Advances in Heterocyclic Aromatic Construction." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0068.

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Abstract:
Rubén Vicente and Luis A. López at the University of Oviedo in Spain reported (Angew. Chem. Int. Ed. 2012, 51, 8063) the synthesis of cyclopropyl furan 2 from alkylidene 1 and styrene by way of a zinc carbene intermediate. The same substrate 1 was also converted (Angew. Chem. Int. Ed. 2012, 51, 12128) to furan 3 via catalysis with tetrahydrothiophene in the presence of benzoic acid by J. Stephen Clark at the University of Glasgow. Xue-Long Hou at the Shanghai Institute of Organic Chemistry discovered (Org. Lett. 2012, 14, 5756) that palladacycle 6 catalyzes the conversion of bicyclic alkene 4 and alkynone 5 to furan 7. A silver-mediated C–H/C–H functionalization strategy for the synthesis of furan 9 from alkyne 8 and ethyl acetoacetate was developed (J. Am. Chem. Soc. 2012, 134, 5766) by Aiwen Lei at Wuhan University. Ning Jiao at Peking University and East China Normal University found (Org. Lett. 2012, 14, 4926) that azide 10 and aldehyde 11 could be converted to either pyrrole 12 or 13 with complete regiocontrol by judicious choice of a metal catalyst. Meanwhile, Michael A. Kerr at the University of Western Ontario developed (Angew. Chem. Int. Ed. 2012, 51, 11088) a multicomponent synthesis of pyrrole 16 involving the merger of nitrone 14 and the donor–acceptor cyclopropane 15. The pyrrole 16 was subsequently converted to an intermediate in the synthesis of the cholesterol-lowering drug compound Lipitor. A robust synthesis of the ynone trifluoroboronate 17 was developed (Org. Lett. 2012, 14, 5354) by James D. Kirkham and Joseph P.A. Harrity at the University of Sheffield, which thus allowed for the ready production of trifluoroboronate-substituted pyrazole 18. An alternative pyrazole synthesis via oxidative closure of unsaturated hydrazine 19 to produce 20 was reported (Org. Lett. 2012, 14, 5030) by Yu Rao at Tsinghua University. A unique fluoropyrazole construction was developed (Angew. Chem. Int. Ed. 2012, 51, 12059) by Junji Ichikawa at the University of Tsukuba that involved nucleophilic substitution of two of the fluorides in 21 to form pyrazole 22.
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Anderson, E. A., and B. Gockel. "Variation 2: Ring Expansion of Donor–Acceptor-Substituted Cyclopropanes." In Science of Synthesis Knowledge Updates KU 2010/4, 1. Georg Thieme Verlag KG, 2010. http://dx.doi.org/10.1055/sos-sd-129-00093.

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Reißig, H. U. "Donor-Acceptor-Substituted Cyclopropanes: Versatile Building Blocks in Organic Synthesis." In Small Ring Compounds in Organic Synthesis III, 73–136. De Gruyter, 1987. http://dx.doi.org/10.1515/9783112597521-004.

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Conference papers on the topic "Donor-Acceptor cyclopropane"

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Chagarovskiy, Alex, Olga Ivanova, and Igor Trushkov. "Donor-acceptor cyclopropanes with nucleophilic group at ortho-position of donor aromatic substituent." In PROCEEDINGS OF INTERNATIONAL CONFERENCE ON RECENT TRENDS IN MECHANICAL AND MATERIALS ENGINEERING: ICRTMME 2019. AIP Publishing, 2020. http://dx.doi.org/10.1063/5.0018466.

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