Relevant bibliographies by topics / Cycloadditions aza-Diels–Alder

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Academic literature on the topic 'Cycloadditions aza-Diels–Alder'

Author: Grafiati
Published: 25 May 2024

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Journal articles on the topic "Cycloadditions aza-Diels–Alder"

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Heredia-Moya, Jorge, Daniel A. Zurita, José Eduardo Cadena-Cruz, and Christian D. Alcívar-León. "Diaza-1,3-butadienes as Useful Intermediate in Heterocycles Synthesis." Molecules 27, no. 19 (October 9, 2022): 6708. http://dx.doi.org/10.3390/molecules27196708.

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Many heterocyclic compounds can be synthetized using diaza-1,3-butadienes (DADs) as key structural precursors. Isolated and in situ diaza-1,3-butadienes, produced from their respective precursors (typically imines and hydrazones) under a variety of conditions, can both react with a wide range of substrates in many kinds of reactions. Most of these reactions discussed here include nucleophilic additions, Michael-type reactions, cycloadditions, Diels–Alder, inverse electron demand Diels–Alder, and aza-Diels–Alder reactions. This review focuses on the reports during the last 10 years employing 1,2-diaza-, 1,3-diaza-, 2,3-diaza-, and 1,4-diaza-1,3-butadienes as intermediates to synthesize heterocycles such as indole, pyrazole, 1,2,3-triazole, imidazoline, pyrimidinone, pyrazoline, -lactam, and imidazolidine, among others. Fused heterocycles, such as quinazoline, isoquinoline, and dihydroquinoxaline derivatives, are also included in the review.
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Presset, Marc, Michel Rajzmann, Guillaume Dauvergne, Jean Rodriguez, and Yoann Coquerel. "Periselectivity in the Aza-Diels–Alder Reaction of 1-Azadienes with α-Oxoketenes: A Combined Experimental and Theoretical Study." Molecules 25, no. 20 (October 20, 2020): 4811. http://dx.doi.org/10.3390/molecules25204811.

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Inversions in the periselectivity of formal aza-Diels–Alder cycloadditions between α-oxoketenes generated by a thermally-induced Wolff rearrangement and 1-azadienes were observed experimentally as a function of the α-oxoketene and the 1-azadiene, as well as the reaction temperature and time. Some unexpected inversion in the diastereoselectivity was observed, too. These variations in selectivities were fully rationalized by computational modeling using density functional theory (DFT) methods.
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Skrzyńska, Anna, Sebastian Frankowski, and Łukasz Albrecht. "Cyclic 1‐Azadienes in the Organocatalytic Inverse‐Electron‐Demand Aza‐Diels‐Alder Cycloadditions." Asian Journal of Organic Chemistry 9, no. 11 (September 4, 2020): 1688–700. http://dx.doi.org/10.1002/ajoc.202000332.

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4

CHEMOURI, HAFIDA, WAFAA BENCHOUK, and SIDI MOHAMED MEKELLECHE. "REGIOSELECTIVITY OF HETERO DIELS–ALDER REACTIONS BETWEEN 1-AZA-1,3-BUTADIENE DERIVATIVES AND DIMETHYLVINYLAMINE: A THEORETICAL INVESTIGATION." Journal of Theoretical and Computational Chemistry 05, no. 04 (December 2006): 707–18. http://dx.doi.org/10.1142/s0219633606002581.

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The regioselectivity of hetero Diels–Alder reactions between 1-aza-1,3-butadiene derivatives and dimethylvinylamine is elucidated by means of several theoretical approaches, namely, the Gazquez–Mendez rule based on the calculation of local softnesses, barrier activation calculations, maximum hardness principle, and the Houk rule based on the FMO theory. The calculations were performed at the B3LYP/6-31G(d) level of theory, and the obtained results are in agreement with available experimental results. Moreover, the present analysis shows that these inverse electron demand polar cycloadditions present a linear relationship between the activation barriers of the favored ortho regio-isomers and the inverse of electrophilicity differences of the reagents.
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Sousa, Carlos A. D., M. Luísa C. Vale, José E. Rodríguez-Borges, Xerardo Garcia-Mera, and Jesús Rodríguez-Otero. "Acid-catalyzed aza-Diels–Alder versus 1,3-dipolar cycloadditions of methyl glyoxylate oxime with cyclopentadiene." Tetrahedron Letters 49, no. 40 (September 2008): 5777–81. http://dx.doi.org/10.1016/j.tetlet.2008.07.110.

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6

Mayr, Herbert, Armin R. Ofial, Jürgen Sauer, and Bernhard Schmied. "[2++4] Cycloadditions of Iminium Ions − Concerted or Stepwise Mechanism of Aza Diels−Alder Reactions?" European Journal of Organic Chemistry 2000, no. 11 (June 2000): 2013–20. http://dx.doi.org/10.1002/1099-0690(200006)2000:11<2013::aid-ejoc2013>3.0.co;2-a.

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7

Blanco-Carapia, Roberto E., Enrique A. Aguilar-Rangel, Mónica A. Rincón-Guevara, Alejandro Islas-Jácome, and Eduardo González-Zamora. "Synthesis of New Polyheterocyclic Pyrrolo[3,4-b]pyridin-5-ones via an Ugi-Zhu/Cascade/Click Strategy." Molecules 28, no. 10 (May 14, 2023): 4087. http://dx.doi.org/10.3390/molecules28104087.

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A diversity-oriented synthesis (DOS) of two new polyheterocyclic compounds was performed via an Ugi-Zhu/cascade (N-acylation/aza Diels-Alder cycloaddition/decarboxylation/dehydration)/click strategy, both step-by-step to optimize all involved experimental stages, and in one pot manner to evaluate the scope and sustainability of this polyheterocyclic-focused synthetic strategy. In both ways, the yields were excellent, considering the high number of bonds formed with release of only one carbon dioxide and two molecules of water. The Ugi-Zhu reaction was carried out using the 4-formylbenzonitrile as orthogonal reagent, where the formyl group was first transformed into the pyrrolo[3,4-b]pyridin-5-one core, and then the remaining nitrile group was further converted into two different nitrogen-containing polyheterocycles, both via click-type cycloadditions. The first one used sodium azide to obtain the corresponding 5-substituted-1H-tetrazolyl-pyrrolo[3,4-b]pyridin-5-one, and the second one with dicyandiamide to synthesize the 2,4-diamino-1,3,5-triazine-pyrrolo[3,4-b]pyridin-5-one. Both synthesized compounds may be used for further in vitro and in silico studies because they contain more than two heterocyclic moieties of high interest in medicinal chemistry, as well as in optics due to their high π-conjugation.
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8

Fillion, Houda, Félix Pautet, Pascal Nebois, and Zouhair Bouaziz. "Cycloadditions of α,β-Unsaturated N,N-Dimethylhydrazones. A Diels-Alder Strategy for the Building of Aza-Hetero Rings." HETEROCYCLES 54, no. 2 (2001): 1095. http://dx.doi.org/10.3987/rev-00-sr(i)5.

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9

Ntirampebura, Deogratias, and Léon Ghosez. "Cycloadditions of 2-aza-1,3-dienes to aldehydes: a Diels-Alder strategy for the diastereoselective hydroxyalkylation of carboxylic acid derivatives." Tetrahedron Letters 40, no. 39 (September 1999): 7079–82. http://dx.doi.org/10.1016/s0040-4039(99)01444-6.

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10

Palacios, Francisco, Concepción Alonso, Patricia Amezua, and Gloria Rubiales. "Synthesis of Aza Polycyclic Compounds Derived from Pyrrolidine, Indolizidine, and Indole via Intramolecular Diels−Alder Cycloadditions of Neutral 2-Azadienes." Journal of Organic Chemistry 67, no. 6 (March 2002): 1941–46. http://dx.doi.org/10.1021/jo016325v.

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Dissertations / Theses on the topic "Cycloadditions aza-Diels–Alder"

1

Castro, Agudelo Brian Alejandro. "Arynes as short-lived intermediates for the synthesis of nucleosides and N-doped PAHs." Electronic Thesis or Diss., Aix-Marseille, 2021. http://www.theses.fr/2021AIXM0182.

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La chimie des ortho-arynes (ou simplement arynes dans la suite de ce manuscrit), c’est-à-dire des arènes contenant formellement une triple liaison dans le cycle aromatique, a connu un regain d'intérêt au cours de la dernière décennie. Les arynes sont des espèces électrophiles très réactives empêchant leur isolement mais permettant leurs réactions avec un grand nombre d'arynophiles. Dans ce manuscrit, nous présentons les tendances actuelles de la chimie des arynes et notre propre travai ldans le domaine. Le but de notre travail était d'explorer l'utilisation de la cycloadditionaza-Diels–Alder entre les arynes et les aldimines comme un outil synthétique pour élaborer des architectures moléculaires originales pour des applications dans différents domaines, de la chimie médicinale aux matériaux. Dans une première approche, des séquences de cycloaddition aza-Diels–Alder / oxydation monotopes ont été développées pour la synthèse de benzo[e]-7-azaindoles protégés, qui ont été convertis en nucléosides par des réactions de couplage avec des dérivés du ribose. L'activité antivirale de ces molécules est à l'étude. Dans une autre approche, des séquences de cyclo addition aza-Diels–Alder/N-arylation en cascade ont été développées pour la synthèse d'hydroisoquinolines N-arylées, qui ont ensuite été converties en hydrocarbures polycycliques cationiques dopés N à chiralité axiale. Quelques unes de leurs propriétés physico-chimiques ont été évaluées par spectroscopies et modélisation. Dans l'ensemble, ces travaux indiquent que les arynes n'ont sans doute pas encore révélés leur plein potentiel en synthèse
The chemistry of ortho-arynes, that are arenes containing formally a triple bond inthe aromatic ring, has experienced a renewed interest in the last decade. Arynes areelectrophilic species with high reactivity precluding their isolation but allowing their reaction with a number of arynophiles. In this manuscript we present the current trends in aryne chemistry and our own work in the field. The aim of our work was to explore the use of the aza-Diels–Alder cycloaddition between arynes and aldimines asa synthetic tool to elaborate original molecular architectures for applications indifferent fields, from medicinal chemistry to materials. In a first approach, some one pot aza Diels-Alder cycloaddition / oxidation sequences were developed for the synthesis of protected benzo[e]-7-azaindoles, which were converted to nucleosides by coupling reaction with ribose derivatives. The antiviral activity of these molecules is under investigation. In another approach some cascade aza-Diels–Aldercycloaddition / N-arylation sequences were developed for the synthesis of N-arylated hydroisoquinolines, which were converted into cationic N-doped axially chiralpolyaromatic hydrocarbons. Some of their physicochemical properties were evaluated by spectroscopy and computational modeling. Over all this work indicates that arynes may not yet have revealed their full potential in synthesis
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Book chapters on the topic "Cycloadditions aza-Diels–Alder"

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Taber, Douglass. "Stereoselective C-N Ring Construction." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0054.

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Ryoichi Kuwano of Kyushu University showed (J. Am. Chem. Soc. 2008, 130, 808) that diastereomerically and enantiomerically pure pyrollidines such as 2 could be prepared by hydrogenation of the corresponding pyrrole. Victor S. Martín of Universidad de la Laguna found (Organic Lett. 2008, 10, 2349) that the stereochemical outcome of the pyrrolidine-forming Nicholas cyclization could be directed by the protecting group on the N. Jianbo Wang of Peking University established (J. Org. Chem. 2008, 73, 1971) a convenient route to diazo esters such as 6. N-H insertion led to the pyrrolidine, which Zhen-Jiang Xu of the Shanghai Institute of Organic Chemistry and Chi-Ming Che of the University of Hong Kong showed (Organic Lett. 2008, 10, 1529) could be reduced with high diastereoselectivity to the hydroxy ester 7. Alternatively, Professor Wang found that photochemical Wolff rearrangement of 6 delivered the pyrrolidone 8 . Martin J. Slater and Shiping Xie of GlaxoSmithKline optimized (J. Org. Chem. 2008, 73, 3094) the hydroquinine catalyzed enantioselective 3+2 cycloaddition of 9 and 10, leading to the pyrrolidine 11 with high diastereocontrol. Shu Kobayashi of the University of Tokyo developed (Adv. Synth. Cat. 2008, 350, 647) a practical protocol for the aza Diels-Alder construction of enantiomerically-pure piperidines such as 14 . Biao Yu of the Shanghai Institute of Organic Chemistry cyclized (Tetrahedron Lett. 2008, 49, 672) the product from the proline-catalyzed enantioselective aldol of 15 and 16, leading to the substituted piperidine 17 . Michael Shipman of the University of Warwick described (Tetrahedron Lett. 2008, 49, 250) the cyclization of the aziridine derived from 18, that proceeded to give 19 as a single diastereomer, apparently via kinetic side-chain protonation. Takeo Kawabata of Kyoto University found (J. Am. Chem. Soc. 2008, 130, 4153) that intramolecular alkylation to form four, five and six-membered rings from amino esters such as 21 proceeded with remarkable enantioretention. Géraldine Masson and Jieping Zhu of CNRS, Gif-sur-Yvette, condensed (Organic Lett. 2008, 10, 1509) cinnamaldehyde 23 with cyanide and an ω-alkenyl amine to give the intramolecular aza-Diels-Alder substrate 24. Hongbin Zhai of the Shanghai Institute of Organic Chemistry acylated (J. Org. Chem. 2008, 73, 3589) 26 with 27, leading to the ring-closing metathesis precursor 28.
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Conference papers on the topic "Cycloadditions aza-Diels–Alder"

1

Rodríguez-Borges, José, Carlos Sousa, M. Luísa Vale, and Xerardo García-Mera. "Aza-Diels-Alder versus 1,3-Dipolar Cycloadditions of Methyl Glyoxylate Oxime with Cyclopentadiene." In The 12th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2008. http://dx.doi.org/10.3390/ecsoc-12-01218.

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