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Добірка наукової літератури з теми "Tandem Cyclization"

Автор: Grafiati
Опубліковано: 6 вересня 2023

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Статті в журналах з теми "Tandem Cyclization"

1

Rae Kim, Hyoung, Su Yeon Jo, Hyoung Cheul Kim, and Dong Ju Jeon. "Tandem Cyclization of Phytosphingosine." HETEROCYCLES 55, no. 6 (2001): 1127. http://dx.doi.org/10.3987/com-01-9187.

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2

Nookaraju, U., Eeshwaraiah Begari, and Pradeep Kumar. "Total synthesis of (+)-monocerin via tandem dihydroxylation-SN2 cyclization and a copper mediated tandem cyanation–lactonization approach." Org. Biomol. Chem. 12, no. 31 (2014): 5973–80. http://dx.doi.org/10.1039/c4ob00965g.

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A simple and novel synthesis of (+)-monocerin was achieved from 3-buten-1-ol employing HKR, Julia olefination, intramolecular tandem Sharpless asymmetric dihydroxylation-SN2 cyclization and a novel copper mediated tandem cyanation–cyclization as the key steps.
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3

Yuan, Lang, and Hai-Tao Yu. "A Density Functional Theory Investigation of the Tandem Radical Cyclization of 1-[2-Yl-3-(2-Methoxyphenyl)-prop-2-enyl]-6-oxo-1,6-dihydropyridine-2-carbonitrile." Australian Journal of Chemistry 69, no. 3 (2016): 319. http://dx.doi.org/10.1071/ch15369.

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A density functional theory investigation of the mechanism of the titled reaction has been performed. The results suggest that the compound 1-[2-iodo-3-(2-methoxyphenyl)-prop-2-enyl]-6-oxo-1,6-dihydropyridine-2-carbonitrile would rather be converted into the titled free radical by deiodination than go by way of a Diels–Alder cycloaddition and HI-elimination to access the experimentally observed product. The deiodination of the radical precursor is followed by tandem radical cyclizations and hydrogen-loss oxidations to generate tetracyclic non-radical products. The mechanism of the tandem reaction was determined by an examination of the calculated reaction barriers, attack trajectories, and interaction energies between key orbitals. Furthermore, the H-loss oxidation of the addition intermediates by several H-abstractors were carefully analyzed. The theoretical results are in close agreement with the available experimental evidence. The detailed reaction mechanism and knowledge of such an intramolecular tandem radical cyclization presented in this study not only provide insight into the nature of tandem cyclizations but also serves as a useful guide for future experimental investigations.
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4

Trost, Barry M., and Serge Mignani. "Tandem palladium-catalyzed elimination-cyclization." Journal of Organic Chemistry 51, no. 18 (September 1986): 3435–39. http://dx.doi.org/10.1021/jo00368a005.

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5

Huang, Ji-Rong, Liu Qin, Yu-Qin Zhu, Qiang Song, and Lin Dong. "Multi-site cyclization via initial C–H activation using a rhodium(iii) catalyst: rapid assembly of frameworks containing indoles and indolines." Chemical Communications 51, no. 14 (2015): 2844–47. http://dx.doi.org/10.1039/c4cc07125e.

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Tandem multi-site cyclization triggered by Rh(iii)-catalyzed C–H activation has been achieved for highly efficient synthesis of spirocycle indolin-3-one (C2-cyclization), benzo[a]carbazole (C3-cyclization) and an unusual indoxyl core (N1-cyclization).
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6

Cao, Ziping, Shan Li, Jie Li, Xin Meng, Huaqing Zhang, Xuejun Sun та Jinmao You. "Gold-catalyzed π-directed regioselective cyclization of bis(o-alkynyl benzyl alcohols): rapid access to dihydroisobenzofuran derivatives". New Journal of Chemistry 40, № 10 (2016): 8211–15. http://dx.doi.org/10.1039/c6nj02066f.

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7

Huo, Xing, Jizhong Fang, Lige Xu, and Bowen Fang. "Synergistic Oxidative Coupling–[3+2] Cyclization of Quinones with Olefins Promoted by Cerium(IV) Sulfate Tetrahydrate." Synlett 28, no. 12 (April 11, 2017): 1491–95. http://dx.doi.org/10.1055/s-0036-1588781.

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Анотація:
A cerium(IV) sulfate tetrahydrate promoted oxidative cyclization of quinones with olefins is developed. It proceeds through a tandem [3+2]-cyclization–oxidative coupling–[3+2]-cyclization process, in which tetrahydrobenzodifurans were conveniently constructed in high yields. Moreover, this method exhibits a good functional-group tolerance and scalability.
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8

Błocka, Aleksandra, Paweł Woźnicki, Marek Stankevič, and Wojciech Chaładaj. "Pd-catalyzed intramolecular addition of active methylene compounds to alkynes with subsequent cross-coupling with (hetero)aryl halides." RSC Advances 9, no. 68 (2019): 40152–67. http://dx.doi.org/10.1039/c9ra08002c.

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Анотація:
A tandem cyclization/coupling of acetylenic active methylene compounds with aryl halides features broad scope and excellent functional group compatibility. Mechanistic studies identified 5-exo-dig cyclization as the rate limiting step.
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9

Hou, Yunlei, Mingze Qin, Xiuxiu Yang, Qi Shen, Yanfang Zhao, Yajing Liu, and Ping Gong. "Palladium-catalyzed three-component tandem cyclization of buta-2,3-dien-1-ol, aryl iodides, and imines: an efficient protocol for the synthesis of oxazolidine derivatives." RSC Advances 7, no. 12 (2017): 7401–5. http://dx.doi.org/10.1039/c6ra27993g.

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An efficient three-component tandem cyclization reaction for the synthesis of highly substituted oxazolidines was achieved through the Pd0-catalyzed cyclization of buta-2,3-dien-1-ol with aryl iodides and imines.
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10

Deng, Danfeng, Dayun Huang, Xiangyu Sun, and Biwen Gao. "Recent Advances in the Tandem Difunctionalization of Alkynes: Mechanism-Based Classification." Synthesis 53, no. 19 (April 19, 2021): 3522–34. http://dx.doi.org/10.1055/a-1486-2158.

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AbstractRecent advances on the tandem difunctionalization of alkynes in the last decade (2010–2020) are summarized into five categories based on the type of mechanism: (1) radical addition and coupling for the synthesis of polysubstituted ketones and alkenes, (2) electrophilic addition of alkynes, (3) reactions mediated by haloalkynes or copper acetylides, (4) the preparation of cyclic compounds via radical processes, palladium-catalyzed reactions or conjugate additions, and (5) cyclic compounds as intermediates in ring openings. Herein, radical, electrophilic and nucleophilic reactions are discussed in detail. We hope this review will help to promote future research in this area. 1 Introduction2 Radical Addition and Coupling3 Electrophilic Addition4 Reactions Mediated by Haloalkynes or Copper Acetylides5 Cyclization6 Cyclization and Ring Opening7 Conclusions
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Дисертації з теми "Tandem Cyclization"

1

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.

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Through this study it has been observed that in contrast to propargyl esters which give cyclopropyl products, the high reactivity of propargyl acetals allows a new tandem cyclization to take place, resulting in bicyclic products. It has also been found that steric effects may cause propargyl acetals to react by unexpected pathways. NMR studies confirmed a particularly high reactivity of propargyl acetal compared to propargyl ester. These results show how molecular diversity can easily be achieved by varying the substrates in gold(I) catalysis.
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2

Lam, Tin Yiu. "Synthesis of indoles via a tandem benzannulation-cyclization strategy." Thesis, Massachusetts Institute of Technology, 2008. http://hdl.handle.net/1721.1/46045.

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Анотація:
Vita.
Thesis (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.
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3

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.

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Анотація:
Thesis (S.B.)--Massachusetts Institute of Technology, Dept. of Chemistry, February 2012.
Cataloged 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.
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4

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.

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Анотація:
Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2013.
Cataloged 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.
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5

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.

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The terpene and terpenoid family of compounds is considered to be the largest group of natural products. These compounds not only display great diversity in their structural features but are also known to have a multitude of biological activities including but not limited to anti-bacterial, anti-cancer, anti-inflammatory, and anti-HIV properties. Remarkably, all the terpenoids formed in nature come from two molecules viz. isopentenyl pyrophosphate and its isomer, dimethylallyl pyrophosphate both consisting of just five carbons but assembled in many ways. Nature utilizes highly efficient, enzyme-mediated cascade reactions to transform simple linear molecules to more complex cyclic scaffolds. Cascade or domino reactions are organic chemistry’s most powerful tools that, if executed correctly, mimic the extreme complexity of reactions occurring in nature. Our group has successfully utilized cationic cascade cyclization reactions, to prepare a large library of natural products along with their analogues. It was during the synthesis of one such natural product that it was discovered that a methoxymethyl (MOM) “protecting group” had been transferred within the same molecule. The optimization of this process not only allowed the synthesis of the desired tricyclic framework but also resulted in the liberated MOM group doing an EAS reaction which gave a new C-C bond. This transferred MOM group was further elaborated to different functional groups. Use of the tandem reaction sequence in an attempt to prepare radulanin E has been described. Total syntheses of two chalcone-based analogous meroterpenoids have been successfully completed using the aforementioned sequence. An advanced intermediate for an entire new class of acridine-based schweinfurthins has been elaborated. The results will be discussed in detail.
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6

Krismanich, 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.

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A set of studies centered around the reactions of the active methine compound 1-carbomethoxy-5-dicyanomethyl-1,3-cyclohexadiene (the "ring-opened adduct"), obtained by base-induced ring-opening of the Diels-Alder adduct of 5,5-dicyanocyclopentadiene and methyl acrylate, has been carried out. A plan was devised for the anionic (at the dicyanomethyl carbon) ring-opened adduct whereby its reaction with electrophiles, for example Michael reactions with double-bond acceptors, would generate reactive intermediates that would undergo cyclization by tandem conjugate addition to the a,ß,?,d-unsaturated ring p-system to generate bicyclic compounds. In practice, reaction with di-tert-butyl methylidenemalonate, methyl vinyl ketone, and cyclopentenone generated intermediates that exhibited greater tandem reactivity than was anticipated: the bicyclic enolates were found to cyclize further by Thorpe-Ziegler-like reaction with the proximal nitrile to generate, after facile acid hydrolysis, substituted known tricyclic skeleta termed homobrendanes, specifically, tricyclo[5. 2. 1. 04,8]decenes. An attempt was made to generalize the reaction to other substrates, among them singly-activated Michael acceptors and 1,2-heteroatom electrophiles, but the generalization of the homobrendane forming reaction did not meet with success. Attempted functional group manipulations to probe the conversion of the homobrendane derived from di-tert-butyl methylidenemalonate to the homobrendane natural product 2-isocyanoallopupukeanane revealed the unreactivity of the skeletal double-bond toward electrophiles and the high reactivity of the ring ketone toward nucleophiles, among them mCPBA which brought about Baeyer-Villiger reaction, and chloride and hydroxide, which brought about addition/elimination reactions to cleave the last-formed homobrendane ring.
The 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.
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7

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.

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8

Xing, 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.

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9

Sandoval, 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.

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10

Yip, 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.

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Частини книг з теми "Tandem Cyclization"

1

Kariv-Miller, Essie, Franco Lombardo, and Lombardo Hatsuo. "The 5,6 vs the 6,5 Electroreductive Tandem Cyclization of Ketones." In Electroorganic Synthesis, 75–81. Boca Raton: Routledge, 2023. http://dx.doi.org/10.1201/9780203758571-11.

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2

Malleron, J. L., J. C. Fiaud, and J. Y. Legros. "Tandem Arylsulfonation-Cyclization Process." In Handbook of Palladium-Catalyzed Organic Reactions, 89–90. Elsevier, 1997. http://dx.doi.org/10.1016/b978-012466615-3/50013-6.

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3

Malleron, J. L., J. C. Fiaud, and J. Y. Legros. "Tandem Chlorination-Cyclization and Tandem Chlorination-Carbonylation-Cyclization of 1,6-Enynes." In Handbook of Palladium-Catalyzed Organic Reactions, 285–87. Elsevier, 1997. http://dx.doi.org/10.1016/b978-012466615-3/50079-3.

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4

Griesbeck, A. G. "Tandem Conjugate Addition and Cyclization." In Quinones and Heteroatom Analogues, 1. Georg Thieme Verlag KG, 2006. http://dx.doi.org/10.1055/sos-sd-028-00633.

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5

Malleron, J. L., J. C. Fiaud, and J. Y. Legros. "Tandem Acyloxylation-Cyclization of 1,5-Dienes." In Handbook of Palladium-Catalyzed Organic Reactions, 198–99. Elsevier, 1997. http://dx.doi.org/10.1016/b978-012466615-3/50046-x.

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6

Malleron, J. L., J. C. Fiaud, and J. Y. Legros. "Tandem Acyloxychlorination-Cyclization of 1,6-Dienes." In Handbook of Palladium-Catalyzed Organic Reactions, 200–201. Elsevier, 1997. http://dx.doi.org/10.1016/b978-012466615-3/50047-1.

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7

Malleron, J. L., J. C. Fiaud, and J. Y. Legros. "Tandem Cyclization-Capture Process of Enynes." In Handbook of Palladium-Catalyzed Organic Reactions, 260–61. Elsevier, 1997. http://dx.doi.org/10.1016/b978-012466615-3/50067-7.

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8

Carter, R. G., and D. L. Kuiper. "Tandem Oxidative Deprotection/Cyclization toward Norhalichondrin." In Stereoselective Reactions of Carbonyl and Imino Groups, 1. Georg Thieme Verlag KG, 2011. http://dx.doi.org/10.1055/sos-sd-202-00479.

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9

Keller, P. A. "Tandem [4 + 2] Cycloadditions and Cyclization." In Six-Membered Hetarenes with One Nitrogen or Phosphorus Atom, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-015-01758.

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10

Carter, R. G., and D. L. Kuiper. "Tandem Iodoetherification/Lewis Acid Catalyzed Cyclization toward Azaspiracid." In Stereoselective Reactions of Carbonyl and Imino Groups, 1. Georg Thieme Verlag KG, 2011. http://dx.doi.org/10.1055/sos-sd-202-00515.

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Тези доповідей конференцій з теми "Tandem Cyclization"

1

Padwa, Albert. "Synthesis of Heterocycles Using Tandem Cyclization Processes." In The 3rd International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 1999. http://dx.doi.org/10.3390/ecsoc-3-01730.

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2

Solorio Alvarado, Cesar, Dipak Patil, María del Gamez Montano, and Marco Ramirez Morales. "SYNTHESIS OF BENZO[<em>b</em>]CARBAZOLS BY TANDEM Au(I)-CATALYZED CYCLIZATION/MIGRATION/CYCLIZATION." In The 24th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2020. http://dx.doi.org/10.3390/ecsoc-24-08402.

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3

Solorio Alvarado, Dr César, and Narendra Mali. "<em>Synthesis Of polyaromatic heterocycles pyrrolo [1,2-a] indoles by Gold(I)-Catalyzed tandem Cyclization/C-H Activation/Cyclization.</em>." In The 24th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2020. http://dx.doi.org/10.3390/ecsoc-24-08378.

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