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Relevant bibliographies by topics / Construction of Heterocyclic and Carbocyclic Rings

Academic literature on the topic 'Construction of Heterocyclic and Carbocyclic Rings'

Author: Grafiati

Published: 6 September 2023

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Journal articles on the topic "Construction of Heterocyclic and Carbocyclic Rings"

1

Cardoso, Ana L., and Maria I. L. Soares. "1,3-Dipolar Cycloadditions Involving Allenes: Synthesis of Five-Membered Rings." Current Organic Chemistry 23, no. 27 (January 15, 2020): 3064–134. http://dx.doi.org/10.2174/1385272823666191203122959.

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The 1,3-dipolar cycloaddition reaction is a powerful and versatile strategy for the synthesis of carbocyclic and heterocyclic five-membered rings. Herein, the most recent developments on the [3+2] cycloaddition reactions using allenes acting either as dipolarophiles or 1,3-dipole precursors, are highlighted. The recent contributions on the phosphine- and transition metal-catalyzed [3+2] annulations involving allenes as substrates are also covered, with the exception of those in which the formation of a 1,3-dipole (or synthetic equivalent) is not invoked. This review summarizes the most relevant research in which allenes are used as building blocks for the construction of structurally diverse five-membered rings via [3+2] annulation reactions.

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Grillo, Alessandro, and Bruno Mattia Bizzarri. "Catalytic Enantioselective Diels Alder Reaction: Application in the Synthesis of Antiviral Agents." Catalysts 12, no. 2 (January 25, 2022): 150. http://dx.doi.org/10.3390/catal12020150.

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The Diels–Alder reaction (DAR) is one of the most effective and reliable strategies for the construction of six-membered carbocyclic and heterocyclic rings, and it is widely used in the synthesis of organic molecules and drugs. Due to the high regio- and stereo-selectivity and its versatility, DARs have represented a powerful tool for organic chemistry for many years. In addition, the asymmetric DAR has become a fundamental synthetic approach in the preparation of optically active six-membered rings and natural compounds. The COVID-19-related pandemic requires continuous research; DAR represents an useful method to obtain optically active intermediates for the synthesis of antiviral agents under different catalytic conditions. We would like to highlight an intriguing synthetic procedure applied to the development of novel synthetic protocols that are potentially useful against a large panel of viruses and other unmet diseases.

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Bognár, Balázs, Györgyi Úr, Cecília Sár, Olga H. Hankovszky, Kálmán Hideg, and Tamás Kálai. "Synthesis and Application of Stable Nitroxide Free Radicals Fused with Carbocycles and Heterocycles." Current Organic Chemistry 23, no. 4 (May 22, 2019): 480–501. http://dx.doi.org/10.2174/1385272823666190318163321.

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Stable nitroxide free radicals have traditionally been associated with 2,2,6,6- tetramethylpiperidine-1-oxyl (TEMPO) or its 4-substituted derivatives as relatively inexpensive and readily accessible compounds with limited possibilities for further chemical modification. Over the past two decades, there has been a resurgence of interest in stable free radicals with proper functionalization tuned for various applications. The objective of this review is to present recent results with synthetic methodologies to achieve stable nitroxide free radicals fused with aromatic carbocycles and heterocycles. There are two main approaches for accessing stable nitroxide free radicals fused with arenes, e.g., isoindoline- like nitroxides: further functionalization and oxidation of phthalimide or inventive functionalization of pyrroline nitroxide key compounds. The latter also offers the constructions of versatile heterocyclic scaffolds (furan, pyrrole, thiophene, 1,2-thiazole, selenophene, pyrazole, pyrimidine, pyridine, pyridazine, 1,5-benzothiazepine) that are fused with pyrroline or tetrahydropyridine nitroxide rings. The possible applications of these new stable nitroxide free radicals, such as covalent spin labels and noncovalent spin probes of proteins and nucleic acids, profluorescent probes, building blocks for construction of dual active drugs and electroactive materials, and substances for controlled free radical polymerization, are discussed.

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Trost, Barry M., Zhongxing Huang, and Ganesh M. Murhade. "Catalytic palladium-oxyallyl cycloaddition." Science 362, no. 6414 (November 1, 2018): 564–68. http://dx.doi.org/10.1126/science.aau4821.

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Exploration of intermediates that enable chemoselective cycloaddition reactions and expeditious construction of fused- or bridged-ring systems is a continuous challenge for organic synthesis. As an intermediate of interest, the oxyallyl cation has been harnessed to synthesize architectures containing seven-membered rings via (4+3) cycloaddition. However, its potential to access five-membered skeletons is underdeveloped, largely due to the thermally forbidden (3+2) pathway. Here, the combination of a tailored precursor and a Pd(0) catalyst generates a Pd-oxyallyl intermediate that cyclizes with conjugated dienes to produce a diverse array of tetrahydrofuran skeletons. The cycloaddition overrides conventional (4+3) selectivity by proceeding through a stepwise pathway involving a Pd-allyl transfer and ring closure sequence. Subsequent treatment of the (3+2) adducts with a palladium catalyst converts the heterocycles to the carbocyclic cyclopentanones.

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Cha, J. K., and J. Oh. "[4 + 3] Cycloaddition Reactions of Cyclic Oxyallyls in Natural Product Synthesis." Current Organic Chemistry 2, no. 3 (May 1998): 217–32. http://dx.doi.org/10.2174/1385272802666220128192145.

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The [4 + 3] cycloadditions of oxyallyls and related allyl cations to 1,3-dienes have been widely utilized for the stereocontrolled construction of seven-membered carbocycles. By virtue of the spectator skeleton, the key variant of utilizing cyclic oxyallyls, i.e., by embedding an oxyallyl function in cyclic compounds, provides a conceptually attractive and operationally efficient route to other medium-sized carbocycles and heterocycles in addition to seven-membered rings. The resulting architecturally complex, polycyclic cycloadducts contain not only sufficient functionality, but also well defined facial differentiation useful for subsequent elaboration.

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Chen, Feng-Zheng, Qing-Xiang Xiang, Yuan-Qin Zhang, and Jun-Ru Xiong. "(1β,2α,3α,7α,11α,13β)-1,3,7,11-Tetraacetoxy-2,13-bis(benzyloxy)-21-methyl-19,21-secohetisan-19-al hemihydrate." Acta Crystallographica Section E Structure Reports Online 65, no. 6 (May 29, 2009): o1432. http://dx.doi.org/10.1107/s1600536809018315.

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In the crystal structure of the title compound, C43H46NO13·0.5H2O, the molecule assumes a U-shaped conformation, the terminal benzene rings being approximately parallel and partially overlapped with each other. The molecule contains eight alicyclic and heterocyclic rings. The cyclohexane rings adopt chair conformations, the other three six-membered carbocyclic rings form a bicyclo[2.2.2]octane system with a boat conformation for each six-membered ring, the six-membered heterocyclic ring has a chair conformation and both of the five-membered rings have envelope conformations. The solvent water molecule links with the organic moleculeviaclassic O—H...O and weak C—H...O hydrogen bonding in the crystal structure.

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Boyd, Derek R., Narain D. Sharma, Ludmila V. Modyanova, Jonathan G. Carroll, John F. Malone, Christopher CR Allen, John TG Hamilton, David T. Gibson, Rebecca E. Parales, and Howard Dalton. "Dioxygenase-catalyzed cis-dihydroxylation of pyridine-ring systems." Canadian Journal of Chemistry 80, no. 6 (June 1, 2002): 589–600. http://dx.doi.org/10.1139/v02-062.

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Toluene dioxygenase-catalyzed dihydroxylation, in the carbocyclic rings of quinoline, 2-chloroquinoline, 2-methoxyquinoline, and 3-bromoquinoline, was found to yield the corresponding enantiopure cis-5,6- and -7,8-dihy dro diol metabolites using whole cells of Pseudomonas putida UV4. cis-Dihydroxylation at the 3,4-bond of 2-chloroquino line, 2-methoxyquinoline, and 2-quinolone was also found to yield the heterocyclic cis-dihydrodiol metabolite, (+)-cis-(3S,4S)-3,4-dihydroxy-3,4-dihydro-2-quinolone. Heterocyclic cis-dihydrodiol metabolites, resulting from dihydroxylation at the 5,6- and 3,4-bonds of 1-methyl 2-pyridone, were isolated from bacteria containing toluene, naphthalene, and biphenyl dioxygenases. The enantiomeric excess (ee) values (>98%) and the absolute configurations of the carbocyclic cis-dihydrodiol metabolites of quinoline substrates (benzylic R) and of the heterocyclic cis-diols from quinoline, 2-quinolone, and 2-pyridone substrates (allylic S) were found to be in accord with earlier models for dioxygenase-catalyzed cis-dihydroxylation of carbocyclic arenes. Evidence favouring the dioxygenase-catalyzed cis-dihydroxylation of pyridine-ring systems is presented.Key words: dioxygenases; cis-dihydroxylation, pyridines, 2-pyridones, absolute configurations.

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Taticchi, Aldo, Lucio Minuti, Daniela Lanari, Assunta Marrocchi, Ilaria Tesei, and Eszter Gacs-Baitz. "Synthesis of helical [2.2]paracyclophanes containing carbocyclic and heterocyclic five-membered rings." Tetrahedron 60, no. 51 (December 2004): 11759–64. http://dx.doi.org/10.1016/j.tet.2004.09.114.

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Liu, Yuxiao, Yu Liu, Charles S. Shanahan, Xichen Xu, and Michael P. Doyle. "A survey of enoldiazo nucleophilicity in selective C–C bond forming reactions for the synthesis of natural product-like frameworks." Org. Biomol. Chem. 12, no. 28 (2014): 5227–34. http://dx.doi.org/10.1039/c4ob00709c.

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Yadav, Deepak, and Rajeev S. Menon. "Recent developments in the chemistry of allenyl sulfones." Organic & Biomolecular Chemistry 18, no. 3 (2020): 365–78. http://dx.doi.org/10.1039/c9ob01912j.

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Allenyl sulfones are versatile building blocks for the construction of various acyclic, carbocyclic and heterocyclic motifs. Recent developments in the preparation and synthetic applications of allenyl sulfones are summarised.

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Dissertations / Theses on the topic "Construction of Heterocyclic and Carbocyclic Rings"

1

White, Andrew Jonathan. "The development of novel photocycloaddition reactions for carbo- and heterocyclic synthesis." Thesis, University of East Anglia, 2000. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.323289.

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Worakun, Tanachat. "Palladium and rhodium catalysed construction of carbocyclic and heterocyclic compounds." Thesis, Queen's University Belfast, 1986. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.317069.

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Hanchate, Vinayak. "Sulfoximine and Sulfoxonium Ylide Directed C-H Activation and Domino Cyclization: Construction of Heterocyclic and Carbocyclic Rings." Thesis, 2020. https://etd.iisc.ac.in/handle/2005/5074.

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The thesis presents the construction of heterocyclic and carbocyclic rings using rhodium-catalyzed C-H bond activation followed by a tandem cyclization strategy. This involves the synthesis of heterocyclic compounds such as 1,2-benzothiazine using sulfoximine directed Rh(III)-catalyzed C-H activation and tandem [4+2] annulation with arylalkynyl silanes. A poly-heterocyclic furanone-fused 1,2-benzothiazine is synthesized using 4-hydroxy-2-alkynoate as a coupling partner using sulfoximine as a directing group by domino C-H activation, [4+2] annulation, and lactonization. The thesis also involves the synthesis of carbocycles such as furanone fused 1-naphthols by Rh(III)-catalyzed domino C-H activation, [4+2] annulation, and followed by lactonization using sulfoxonium ylide as a traceless carbenoid based directing group. In this Rh(III)-catalyzed C-H activation, sulfoxonium ylide is used as a directing group for the synthesis of 3-substituted indonone derivatives, which also involves a tandem [4+1] annulation. In this study, sulfoxonium ylide acts as a traceless directing group and internal oxidant. Therefore, external metal oxidants are not required, and the byproduct obtained is DMSO, which can be easily removed. Sulfoxonium ylide was also used as a directing group for the synthesis of 2H-cyclopropa[b]naphthalen-2-one carbocyclic scaffolds using allylates as coupling partners. This reaction proceeded via domino Rh(III)-catalyzed, [4+2] annulation, and cyclopropanation.
CSIR, SERB (EMR/2016/006358)

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4

Smith, Christopher Dennis. "Development of formal inverse electron demand Diels-Alder and electrocyclic reactions for the construction of carbocyclic and heterocyclic compounds." 2009. http://link.library.utoronto.ca/eir/EIRdetail.cfm?Resources__ID=968433&T=F.

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Books on the topic "Construction of Heterocyclic and Carbocyclic Rings"

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Worakun, Tanachat. Palladium and rhodium catalysed construction of carbocyclic and heterocyclic compounds. 1987.

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Book chapters on the topic "Construction of Heterocyclic and Carbocyclic Rings"

1

"Stereoselective Construction of Carbocyclic Rings." In Organic Synthesis, 202–3. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2006. http://dx.doi.org/10.1002/0470056312.ch102.

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2

Taber, Douglass. "Enantioselective Organocatalyzed Construction of Carbocyclic Rings." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0072.

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One of the most practical ways to construct enantiomerically-enriched carbocyclic systems is to effect asymmetric transformation of preformed prochiral rings. Choon-Hong Tan of the National University of Singapore observed (Chem. Commun. 2008, 5526) that allylic halides such as 1 coupled with malonates such as 2 to give the α-methylene ketone 3 in high ee. Xinmiao Liang of the Dalian Institute of Chemical Physics and Jinxing Ye of the East China University of Science and Technology reported (Chem. Commun. 2008, 3302) that nitromethane 5 could be added to enones such as 4 to construct cyclic quaternary stereogenic centers such as that of 6. The addition of the cyclohexanone 7 to the acceptor 8 described (Chem. Commun. 2008, 6315) by Yixin Lu, also of the National University of Singapore led to the creation of two new cyclic stereogenic centers. Polycarbocyclic prochiral rings are also of interest. Teck-Peng Loh of Nanyang Technological University devised (Tetrahedron Lett. 2008, 49, 5389) the steroid AB donor 10, that added to crotonaldehyde 1 to give the single enantiomerically-pure diastereomer 12. Nitro alkenes are excellent Michael acceptors. Dieter Enders of RWTH Aachen took advantage of this (Angew. Chem. Int. Ed. 2008, 47, 7539) in developing the addition of aldehydes such as 14 to the nitroalkene 13. Intramolecular alkylation ensued, to deliver the product 15 as a single diastereomer. Guofu Zhong, also of Nanyang Technological University, established (Organic Lett. 2008, 10, 3425; Organic Lett. 2008, 10, 3489) an approach to cyclopentane construction based on the Michael addition of β-ketoesters such as 16 and 19 to nitroalkenes such as 17 and 20. Intramolecular nitro aldol (Henry) addition led to 18, while an intramolecular Michael addition delivered 21. Damien Bonne and Jean Rodriguez of Aix-Marseille Université employed (Organic Lett. 2008, 10, 5409) intramolecular dipolar cycloaddition to convert the initial adduct between 22 and 23 to the cyclopentane 24. They also prepared cyclohexane derivatives using this approach. The diketone 25 is prochiral. Benjamin List of the Max-Planck Institut, Mülheim devised (Angew. Chem. Int. Ed. 2008, 47, 7656) an organocatalyst that mediated the intramolecular aldol cyclization of 25 to 26 in high ee.

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Graham, A., and M. Robinson. "Tricyclic Systems: Central Carbocyclic Ring with Fused Five-membered Rings." In Comprehensive Heterocyclic Chemistry III, 1135–99. Elsevier, 2008. http://dx.doi.org/10.1016/b978-008044992-0.00921-4.

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Buckley, B. R. "Tricyclic Systems: Central Carbocyclic Ring with Fused Six-membered Rings." In Comprehensive Heterocyclic Chemistry III, 1229–68. Elsevier, 2008. http://dx.doi.org/10.1016/b978-008044992-0.00923-8.

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McKinnon, David M. "Tricyclic Systems: Central Carbocyclic Ring with Fused Five-membered Rings." In Comprehensive Heterocyclic Chemistry II, 841–74. Elsevier, 1996. http://dx.doi.org/10.1016/b978-008096518-5.00165-9.

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Nichol, Kenneth J. "Tricyclic Systems: Central Carbocyclic Ring with Fused Six-membered Rings." In Comprehensive Heterocyclic Chemistry II, 921–45. Elsevier, 1996. http://dx.doi.org/10.1016/b978-008096518-5.00167-2.

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7

Taber, Douglass F. "Carbocyclic Construction: The Deng Synthesis of (-)-Plicatic Acid." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0079.

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Tehshik P. Yoon of the University of Wisconsin uncovered (J. Am. Chem. Soc. 2009, 131, 14604) conditions for the crossed photodimerization of acyclic enones. Minoru Isobe of Nagoya University extended (Synlett 2009, 1157) conjugate addition–intramolecular epoxide opening to substrates such as 4, leading to the cyclobutane 6 with high diastereocontrol. In the course of a total synthesis of (+)-brefeldin A, Jinsung Tae of Yonsei University established (Synlett 2009, 1303) conditions for the trans-selective cyclization of 7 to 8. Cyclization with TiCl4 gave the alternative cis diastereomer. Several methods have been put forward for the conversion of carbohydrate derivatives to carbocycles. Yeun-Mi Tsai of the National Taiwan University found (Tetrahedron Lett . 2009, 50, 3805) that acyl silanes such as 9 cyclized efficiently under free radical conditions, leading to the silyl ether 10. Tanmaya Pathak of the Indian Institute of Technology, Kharagpur, developed (Eur. J. Org. Chem. 2009, 872) the tandem conjugate addition– intramolecular alkylation conversion of 11 to 13. Slawomir Jarosz of the Polish Academy of Sciences, Warsawza, observed (Heterocycles 2009, 80, 1303) that the oxime derived from 14 cyclized to 15. The cyclization was accelerated by high pressure. Cyclohexanes can also be prepared from carbohydrates. Tony K. M. Shing of the Chinese University of Hong Kong showed (Organic. Lett. 2009, 11, 5070) that the nitrile oxide derived from 16 cyclized to 17, that he carried on to (-)-gabosine O. John K. Gallos of the Aristotle University of Thessaloniki described (Tetrahedron Lett. 2009, 50, 6916) related work. Paul E. Floreancig of the University of Pittsburgh devised (Organic. Lett. 2009, 11, 3152) conditions for the oxidative cyclization of 18 to 19. Ring closure proceeded with high equatorial selectivity. Kou Hiroya of Tohoku University found (J. Org. Chem. 2009, 74, 6623) that the single oxygenated stereogenic center of 20 directed the dissolving metal reduction–enolate trapping, leading to 21. Similarly, Susumu Kobayashi of the Tokyo University of Science showed (Synlett 2009, 1605) that the oxygenated stereogenic centers of 22 set the alkylated centers of 23. Many marine organisms are able to carry out brominative and chlorinative polyolefin cyclizations.

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"Thiophene Systems Containing Three or More Carbocyclic Fused Rings." In Chemistry of Heterocyclic Compounds: A Series Of Monographs, 315–55. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2008. http://dx.doi.org/10.1002/9780470186565.ch6.

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9

Groziak, M. P. "Tricyclic Systems: Central Carbocyclic Ring with Fused Five- and Six-membered Rings." In Comprehensive Heterocyclic Chemistry III, 1201–28. Elsevier, 2008. http://dx.doi.org/10.1016/b978-008044992-0.00922-6.

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10

Groziak, Michael P., and Frederick G. Jacobs. "Tricyclic Systems: Central Carbocyclic Ring with Fused Five- and Six-membered Rings." In Comprehensive Heterocyclic Chemistry II, 875–919. Elsevier, 1996. http://dx.doi.org/10.1016/b978-008096518-5.00166-0.

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