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Journal articles on the topic 'Diels-Alder type reactions'

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Published: 4 June 2021

Last updated: 7 February 2022

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1

Ayadi, Sameh, and Manef Abderrabba. "Étude DFT des réactions de cycloaddition de type Diels–Alder sur le 4-aza-6-nitrobenzofuroxane." Canadian Journal of Chemistry 85, no. 5 (2007): 331–35. http://dx.doi.org/10.1139/v07-026.

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The purpose of this work is a theoretical study of Diels–Alder reactions between the 4-aza-6-nitrobenzofuroxan 1 with a series of dienophiles 3a–3c. From a thermodynamic and orbital point of view, we discuss the reactivity and the stereoselectivty of these reactions. Activation barriers in the Diels-Alder reactions of compound 1 with a series of dienophiles 3a–3c have been calculated and discussed.Key words: inverse electron demand Diels–Alder (IEDDA), DFT method, 4-aza-6-nitrobenzofuroxane.

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2

Cabrera-Trujillo, Jorge Juan, and Israel Fernández. "Understanding exo-selective Diels–Alder reactions involving Fischer-type carbene complexes." Organic & Biomolecular Chemistry 17, no. 11 (2019): 2985–91. http://dx.doi.org/10.1039/c9ob00132h.

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3

Minuti, Lucio, Roberta Selvaggi, Aldo Taticchi, Ming Guo, and Ernest Wenkert. "Diels–Alder reactions of bicyclic, heteroannular dienones." Canadian Journal of Chemistry 70, no. 5 (1992): 1481–85. http://dx.doi.org/10.1139/v92-183.

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Aluminum chloride catalyzed Diels–Alder reactions of bicyclic dienones of the hexalone type with 1,3-butadiene, isoprene, (E)-piperylene, and (E)-1-methoxy-1,3-butadiene are described. Structure analysis of the adducts by NMR spectroscopy is presented. The site-, endo–exo-, and face-selectivity of the reactions are discussed.

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4

Kell, Arnold J., Christopher C. Montcalm, and Mark S. Workentin. "Photogeneration of a diene template for surface DielsAlder reactions: Photoenolization of an ortho-methyl-benzophenone-modified Au cluster." Canadian Journal of Chemistry 81, no. 6 (2003): 484–94. http://dx.doi.org/10.1139/v03-031.

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A series of monolayer-protected clusters (MPCs) modified with a photoreactive [4-(11-mercaptoundecyl)-phenyl](2-methylphenyl)methanone (1) moiety have been prepared where 1 is co-absorbed to the MPC surface with dodecanethiol, octadecanethiol, or 11-mercaptoundecanoic acid methyl ester. Upon irradiation the MPC-anchored 1 reacts efficiently through its triplet excited states, yielding 1,4-biradicals that collapse to synthetically useful, long-lived photodienol intermediates, which can be efficiently trapped in DielsAlder type chemistry by dienophiles namely, dimethyl acetylenedicarboxylate

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5

Hornung, Christian H., Miguel Á. Álvarez-Diéguez, Thomas M. Kohl, and John Tsanaktsidis. "Diels–Alder reactions of myrcene using intensified continuous-flow reactors." Beilstein Journal of Organic Chemistry 13 (January 19, 2017): 120–26. http://dx.doi.org/10.3762/bjoc.13.15.

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This work describes the Diels–Alder reaction of the naturally occurring substituted butadiene, myrcene, with a range of different naturally occurring and synthetic dienophiles. The synthesis of the Diels–Alder adduct from myrcene and acrylic acid, containing surfactant properties, was scaled-up in a plate-type continuous-flow reactor with a volume of 105 mL to a throughput of 2.79 kg of the final product per day. This continuous-flow approach provides a facile alternative scale-up route to conventional batch processing, and it helps to intensify the synthesis protocol by applying higher reacti

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6

Still, Ian W. J., та Donna Kaye T. Wilson. "α-Oxosulfines: reactions with alkenes and alkynes". Canadian Journal of Chemistry 70, № 3 (1992): 964–73. http://dx.doi.org/10.1139/v92-129.

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Thiochroman-4-one 1,1-dioxide has been successfully converted into 3-sulfinylthiochroman-4-one 1,1-dioxide and the reactions of this α-oxosulfine with a series of alkenes have been carefully investigated. The α-oxosulfine was found to react as a Diels–Alder diene with 2-methylpropene, Z- and E-2-butene, 2-ethyl-1-butene, 1-pentene, Z-2-pentene, and cyclopentene and cyclohexene to produce a new group of heterocyclic compounds, the 2,3-dihydro-5H-1,4-oxathiino[3,2-c][1]benzothiopyrans, in yields ranging from 21 to 42%. In all cases, formation of the Diels–Alder adduct was accompanied by a second

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7

Vichard, Dominique, Taoufik Boubaker, François Terrier, Marie-José Pouet, Julian M. Dust та Erwin Buncel. "The versatile reactivity of 2-aryl-4,6-dinitrobenzotriazole 1-oxides in Diels-Alder type condensations and in σ-complexation - A relationship between superelectrophilicity and pericyclic reactivity". Canadian Journal of Chemistry 79, № 11 (2001): 1617–23. http://dx.doi.org/10.1139/v01-020.

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A two-pronged study of a series of 2-aryl-4,6-dinitrobenzotriazole 1-oxide substrates (2ac) is reported: DielsAlder type pericyclic reactivity and covalent hydration to yield Meisenheimer type hydroxy anionic σ-adducts. The most activated benzotriazole 1-oxide 2a is found to exhibit both dienophilic and heterodienic behaviour on treatment with cyclopentadiene, providing a highly functionalized stereoselective diadduct (7). This diadduct is shown to be the result of two consecutive inverse demand DielsAlder condensations proceeding through the endo mode with a trans addition of two cyclopent

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8

Suzuki, Ichiro, Masafumi Ando, Rumiko Shimabara, Ai Hirata, and Kei Takeda. "A novel hydrazide type organocatalyst for enantioselective Diels–Alder reactions." Organic & Biomolecular Chemistry 9, no. 8 (2011): 3033. http://dx.doi.org/10.1039/c0ob01138j.

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9

Chou, Ta-shue, Hong-Chuan Chen, Woei-Chang Yang, Wan-Sheung Li, Ito Chao, and Shwu-Jiuan Lee. "Type-Two Intramolecular Diels−Alder Reactions of Pyrazolo-o-quinodimethanes." Journal of Organic Chemistry 65, no. 18 (2000): 5760–67. http://dx.doi.org/10.1021/jo9917285.

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10

Xuan, Wen-Jing, Candice Botuha, Bernold Hasenknopf, and Serge Thorimbert. "Chiral Dawson-Type Hybrid Polyoxometalate Catalyzes Enantioselective Diels-Alder Reactions." Chemistry - A European Journal 21, no. 46 (2015): 16512–16. http://dx.doi.org/10.1002/chem.201502839.

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11

Kan, Toshiyuki, and Yasufumi Ohfune. "Internal activation of acrylate-type dienophiles in Diels-Alder reactions." Tetrahedron Letters 36, no. 6 (1995): 943–46. http://dx.doi.org/10.1016/0040-4039(94)02379-p.

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12

Mancini, Pedro M. E., Carla M. Ormachea, and María N. Kneeteman. "Polar Diels-Alder Reactions Under Microwave Irradiation Employing Different Heterocyclic Compounds as Electrophiles." Mini-Reviews in Organic Chemistry 16, no. 6 (2019): 527–43. http://dx.doi.org/10.2174/1570193x15666180608083925.

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During the last twenty years, our research group has been working with aromatic nitrosubstituted compounds acting as electrophiles in Polar Diels-Alder (P-DA) reactions with different dienes of diverse nucleophilicity. In this type of reaction, after the cycloaddition reaction, the nitrated compounds obtained as the [4+2] cycloadducts suffer cis-extrusion with the loss of nitrous acid and a subsequent aromatization. In this form, the reaction results are irreversible. On the other hand, the microwave-assisted controlled heating become a powerful tool in organic synthesis as it makes the reacti

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13

Campi, EM, and WR Jackson. "The Stereochemistry of Organometallic Compounds. XXXIII. Preparation and Reactions of Some Substituted Buta-1,3-Dienes." Australian Journal of Chemistry 42, no. 4 (1989): 471. http://dx.doi.org/10.1071/ch9890471.

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Hydroformylation and hydrocyanation of 2-methylhex-1-en-3-yne surprisingly both involve addition to the alkyne leading to the formation of formyl- and cyano-buta-1,3-dienes whose reactivity in Diels-Alder and ene-type reactions has been investigated.

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14

Ward, Dale E., Thomas E. Nixey, Yuanzhu Gai, Matthew J. Hrapchak, and M. Saeed Abaee. "Intramolecular Diels–Alder reactions of 2H-thiopyran dienes." Canadian Journal of Chemistry 74, no. 7 (1996): 1418–36. http://dx.doi.org/10.1139/v96-160.

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A systematic survey of IMDA reactions of 4-[tris(2-methylethyl)silyl]oxy-2H-thiopyran derivatives with potential dienophiles tethered at the C-2, C-3, C-5, and C-6 positions is presented. Cycloaddition was not observed with a C3 or C4 tether and an unactivated terminal olefin as dienophile. IMDA adducts could be obtained when dienophiles activated by a carbomethoxy group were employed. Compounds having the activated dienophile attached via a C3 tether to C-2 of the 2H-thiopyran gave adducts with high stereoselectivity. Substrates having the dienophile attached to C-3 with a C3 or C4 tether cyc

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15

Späte, Anne-Katrin, Verena F. Schart, Julia Häfner, Andrea Niederwieser, Thomas U. Mayer, and Valentin Wittmann. "Expanding the scope of cyclopropene reporters for the detection of metabolically engineered glycoproteins by Diels–Alder reactions." Beilstein Journal of Organic Chemistry 10 (September 22, 2014): 2235–42. http://dx.doi.org/10.3762/bjoc.10.232.

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Monitoring glycoconjugates has been tremendously facilitated by the development of metabolic oligosaccharide engineering. Recently, the inverse-electron-demand Diels–Alder reaction between methylcyclopropene tags and tetrazines has become a popular ligation reaction due to the small size and high reactivity of cyclopropene tags. Attaching the cyclopropene tag to mannosamine via a carbamate linkage has made the reaction even more efficient. Here, we expand the application of cyclopropene tags to N-acylgalactosamine and N-acylglucosamine derivatives enabling the visualization of mucin-type O-gly

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16

Bräse, Stefan, Nicole Volz, Franziska Gläser, and Martin Nieger. "Highly enantioselective access to cannabinoid-type tricyles by organocatalytic Diels–Alder reactions." Beilstein Journal of Organic Chemistry 8 (August 28, 2012): 1385–92. http://dx.doi.org/10.3762/bjoc.8.160.

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After prosperous domino reactions towards benzopyrans, the products were used as the starting material in Lewis acid catalyzed and organocatalytic Diels–Alder reactions to build up a tricyclic system. Herein, an asymmetric induction up to 96% enantiomeric excess was obtained by the use of imidazolidinone catalysts. This approach can be utilized to construct the tricyclic system in numerous natural products, in particular the scaffold of tetrahydrocannabinol (THC) being the most representative one. Compared with other published methods, condensation with a preexisting cyclohexane moiety in the

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17

Tambar, Uttam K., Sharon K. Lee, and James L. Leighton. "Enantioselective (Formal) Aza-Diels−Alder Reactions with Non-Danishefsky-Type Dienes." Journal of the American Chemical Society 132, no. 30 (2010): 10248–50. http://dx.doi.org/10.1021/ja104480g.

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18

Chou, Ta-shue, and Hong-Chuan Chen. "Type one and type two intramolecular Diels-Alder reactions of quinolono-o-quinodimethanes." Tetrahedron Letters 37, no. 43 (1996): 7823–26. http://dx.doi.org/10.1016/0040-4039(96)01742-x.

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19

Roscales, Silvia, and Joaquín Plumet. "Ring Rearrangement Metathesis in 7-Oxabicyclo[2.2.1]heptene (7-Oxanorbornene) Derivatives. Some Applications in Natural Product Chemistry." Natural Product Communications 12, no. 5 (2017): 1934578X1701200. http://dx.doi.org/10.1177/1934578x1701200517.

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Metathesis reactions is firmly established as a valuable synthetic tool in organic chemistry, clearly comparable with the venerable Diels-Alder and Wittig reactions and, more recently, with the metal-catalyzed cross-coupling reactions. Metathesis reactions can be considered as a fascinating synthetic methodology, allowing different variants regarding substrate (alkene and alkyne metathesis) and type of metathetical reactions. On the other hand, tandem metathesis reactions such Ring Rearrangement Metathesis (RRM) and the coupling of metathesis reaction with other reactions of alkenes such as Di

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20

Polat-Cakir, Sidika, and Ayhan S. Demir. "Hetero Diels–Alder reactions of acyl phosphonates: synthesis of glycosyl type phosphonates." Tetrahedron 67, no. 13 (2011): 2396–401. http://dx.doi.org/10.1016/j.tet.2011.02.007.

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21

Chou, Ta-shue, Hong-Chuan Chen, Woei-Chang Yang, Wan-Sheung Li, Ito Chao, and Shwu-Jiuan Lee. "ChemInform Abstract: Type-Two Intramolecular Diels-Alder Reactions of Pyrazolo-o-quinodimethanes." ChemInform 31, no. 51 (2000): no. http://dx.doi.org/10.1002/chin.200051154.

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22

Suzuki, Ichiro, Masafumi Ando, Rumiko Shimabara, Ai Hirata, and Kei Takeda. "ChemInform Abstract: A Novel Hydrazide Type Organocatalyst for Enantioselective Diels-Alder Reactions." ChemInform 42, no. 34 (2011): no. http://dx.doi.org/10.1002/chin.201134025.

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23

Khorasani, Sanaz, and Manuel Fernandes. "Cooperativity in the Reaction of 9-Methylanthracene With a 1,4-Dithiin Molecule." Acta Crystallographica Section A Foundations and Advances 70, a1 (2014): C913. http://dx.doi.org/10.1107/s205327331409086x.

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Solid-state chemistry involves the manipulation of molecules and materials through photochemical, thermal, or mechanical reaction methods. Single-crystal-to-single-crystal (SCSC) reactions are rare, but offer the opportunity to study reaction mechanisms and molecular motions in the solid state at the atomic level using single crystal X-ray diffraction. This allows the effect of the surrounding molecules, and hence the reaction cavity, on the reacting molecules to be examined which may ultimately lead to postcrystallization methods for creating new materials or reaction products that cannot eas

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24

Banwell, M. G., A. J. Edwards, G. J. Harfoot, et al. "Chemoenzymatic methods for the enantioselective preparation of sesquiterpenoid natural products from aromatic precursors." Pure and Applied Chemistry 75, no. 2-3 (2003): 223–29. http://dx.doi.org/10.1351/pac200375020223.

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The enantiomerically pure cis-1,2-dihydrocatechols 2, which are generated by enzymatic dihydroxylation of the corresponding aromatic, engage in regio- and stereo-controlled Diels-Alder cycloaddition reactions to give a range of synthetically useful bicyclo[2.2.2]octenes. Certain examples of the latter type of compound have been used as starting materials in the synthesis of the sesquiterpenoids (−)-patchoulenone and (−)-hirsutene.

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25

Miyashita, Masaaki. "Recent progress in the synthesis of bioactive polycyclic natural products." Pure and Applied Chemistry 79, no. 4 (2007): 651–65. http://dx.doi.org/10.1351/pac200779040651.

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The zoanthamine alkaloids, a type of heptacyclic marine alkaloid isolated from colonial zoanthids of the genus Zoanthus sp., have distinctive biological and pharmacological properties as well as their unique chemical structures with stereochemical complexity. Namely, norzoanthamine can suppress the loss of bone weight and strength in ovariectomized mice and has been considered a promising candidate for an antiosteoporotic drug, whereas zoanthamine has exhibited potent inhibitory activity toward phorbol myristate-induced inflammation in addition to powerful analgesic effects. Recently, norzoant

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26

Tambar, Uttam K., Sharon K. Lee, and James L. Leighton. "ChemInform Abstract: Enantioselective (Formal) Aza-Diels-Alder Reactions with Non-Danishefsky-Type Dienes." ChemInform 42, no. 2 (2010): no. http://dx.doi.org/10.1002/chin.201102022.

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27

Mattay, Jochen, Joachim Gersdorf, and Jürgen Mertes. "A new type of electron acceptor for Diels–Alder reactions via radical cations." J. Chem. Soc., Chem. Commun., no. 16 (1985): 1088–90. http://dx.doi.org/10.1039/c39850001088.

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28

Constantino, Andre F., Carla S. Francisco, Diana C. Cubides-Roman, and Valdemar Lacerda. "Hetero-Diels-Alder Reactions in the Synthesis of Biologically Active Nitrogen Compounds: A Review." Current Organic Synthesis 15, no. 1 (2018): 84–104. http://dx.doi.org/10.2174/1570179414666170517170230.

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Background: The Hetero-Diels-Alder reaction (HDAR) is a method extensively used in organic chemistry as a tool in the synthesis of innumerous polycyclic compounds in particular nitrogen compounds, presents in many natural products, medicinally relevant substances and organic materials. The literature describes innumerable studies of HDAR using classic methods and modern developments such as reactions on the solid phase, the use of catalysts, transformations in aqueous solution and under microwaves. Objective: This review describes a variety of HDAR focused on obtaining nitrogen-containing comp

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29

Grygorenko, Oleksandr O., Viktoriia S. Moskvina, Oleksandr V. Hryshchuk, and Andriy V. Tymtsunik. "Cycloadditions of Alkenylboronic Derivatives." Synthesis 52, no. 19 (2020): 2761–80. http://dx.doi.org/10.1055/s-0040-1707159.

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The literature on cycloaddition reactions of boron-containing alkenes is surveyed with 132 references. The data are categorized according to the reaction type ([2+1], [2+2], [3+2], [4+2], and [4+3] cycloadditions). The cyclopropanation and the Diels–Alder reactions of alkenylboronic derivatives have been studied more or less comprehensively, and for some substrates, they can be considered as convenient methods for the rapid regio- and stereoselective construction of even complex cyclic systems. Other types of the cycloadditions, as well as mechanistic aspects of the processes, have been addres

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30

Shi, Min, Shi-Cong Cui, and Qing-Jiang Li. "Lithium heptadecafluorooctanesulfonate catalyzed Mannich-type and aza-Diels–Alder reactions in supercritical carbon dioxide." Tetrahedron 60, no. 29 (2004): 6163–67. http://dx.doi.org/10.1016/j.tet.2004.05.065.

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31

Shea, K. J., Kathleen S. Zandi, Andrew J. Staab, and R. Carr. "Disposable tethers in type 2 intramolecular diels-alder cycloaddition reactions. Applications in stereochemical control." Tetrahedron Letters 31, no. 41 (1990): 5885–88. http://dx.doi.org/10.1016/s0040-4039(00)97985-1.

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32

Yoshizawa, Kazunari, Song-Yun Kang, Tokio Yamabe, Akinobu Naka, and Mitsuo Ishikawa. "Thermal Addition of Disilacyclobutenes and Acetylene: A Theoretical Study on Diels−Alder Type Reactions." Organometallics 18, no. 22 (1999): 4637–45. http://dx.doi.org/10.1021/om990316j.

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33

Polat-Cakir, Sidika, and Ayhan S. Demir. "ChemInform Abstract: Hetero Diels-Alder Reactions of Acyl Phosphonates: Synthesis of Glycosyl Type Phosphonates." ChemInform 42, no. 30 (2011): no. http://dx.doi.org/10.1002/chin.201130189.

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34

Rogers, Christine, and Brian A. Keay. "Diastereoselective intramolecular Diels–Alder reactions of the furan diene: the synthesis of (±)-1,4-epoxycadinane." Canadian Journal of Chemistry 71, no. 5 (1993): 611–22. http://dx.doi.org/10.1139/v93-081.

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The diastereoselective intramolecular Diels–Alder reactions of the furan diene (IMDAF), in which the side arm comprises four carbon atoms and is substituted by a methyl group adjacent to, or one carbon removed from, the furan ring, are described. Adducts are formed in moderate to excellent yields when treated with either Florisil in methylene chloride at room temperature or methylaluminum dichloride in methylene chloride at −78 °C. Florisil is most effective for substrates containing unsubstituted dienophiles. An equimolar quantity (1.1 equivalents) of methylaluminum dichloride is most effecti

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35

Delamere, C., C. Jakins, and E. Lewars. "Reactions of oxiranylidene and dimethyloxiranylidene, and their generation by retro Diels–Alder-type reactions: a computational study." Journal of Molecular Structure: THEOCHEM 593, no. 1-3 (2002): 79–91. http://dx.doi.org/10.1016/s0166-1280(02)00144-6.

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36

Bakhtiari, Atefeh, and Javad Safaei-Ghomi. "Effects of Chiral Ligands on the Asymmetric Carbonyl-Ene Reaction." Synlett 30, no. 15 (2019): 1738–64. http://dx.doi.org/10.1055/s-0037-1611875.

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The carbonyl-ene reaction is one of the most well-known reactions for C–C bond formation. Based on frontier molecular orbitals (FMO), carbonyl-ene reactions occur between the highest occupied molecular orbital (HOMO) of the ene compound bearing an active hydrogen atom at the allylic center and the lowest unoccupied molecular orbital (LUMO) of the electron-deficient enophile, which is a carbonyl compound. A high activation barrier enforces the concerted ene reaction rather than a Diels–Alder reaction at high temperature. Employing a catalytic system can eliminate defects in the ene reaction, an

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37

Liu, Hsing-Jang, Yanhong Li, and Eric N. C. Browne. "Face-selective Diels–Alder reactions of (1R,5R)-3-formyl-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-one." Canadian Journal of Chemistry 72, no. 9 (1994): 1883–93. http://dx.doi.org/10.1139/v94-240.

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The stereofacially differentiated enone aldehyde 11 was chosen to study the effects of steric and electronic influence on the Diels–Alder reaction. Under Lewis acid catalysis, 11 adds to dienes at low temperatures at a reasonable rate. Yields of desired chiral adducts are good to high with zinc chloride and boron trifluoride etherate catalysis. In all cases only products of addition to the Re face of general type 27 were observed. The regiochemistry of the adducts is exclusively that predicted by the ortho and para rules. The stereochemistry shows a very high selectivity in favour of aldehyde-

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38

Agramunt, Jordi, Enrique Pedroso, Silvia Kreda, Rudolph Juliano, and Anna Grandas. "Retro-1-Oligonucleotide Conjugates. Synthesis and Biological Evaluation." Molecules 24, no. 3 (2019): 579. http://dx.doi.org/10.3390/molecules24030579.

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Addition of small molecule Retro-1 has been described to enhance antisense and splice switching oligonucleotides. With the aim of assessing the effect of covalently linking Retro-1 to the biologically active oligonucleotide, three different derivatives of Retro-1 were prepared that incorporated a phosphoramidite group, a thiol or a 1,3-diene, respectively. Retro-1–oligonucleotide conjugates were assembled both on-resin (coupling of the phosphoramidite) and from reactions in solution (Michael-type thiol-maleimide reaction and Diels-Alder cycloaddition). Splice switching assays with the resultin

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39

Sugumaran, Manickam, Kubra Umit, Jason Evans, Rachel Muriph, Shosuke Ito, and Kazumasa Wakamatsu. "Oxidative Oligomerization of DBL Catechol, a potential Cytotoxic Compound for Melanocytes, Reveals the Occurrence of Novel Ionic Diels-Alder Type Additions." International Journal of Molecular Sciences 21, no. 18 (2020): 6774. http://dx.doi.org/10.3390/ijms21186774.

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The exposure of human skin to 4-(4-hydroxyphenyl)-2-butanone (raspberry ketone, RK) is known to cause chemical/occupational leukoderma. RK is a carbonyl derivative of 4-(4-hydroxyphenyl)-2-butanol (rhododendrol), a skin whitening agent that was found to cause leukoderma in skin of many consumers. These two phenolic compounds are oxidized by tyrosinase and the resultant products seem to cause cytotoxicity to melanocytes by producing reactive oxygen species and depleting cellular thiols through o-quinone oxidation products. Therefore, it is important to understand the biochemical mechanism of th

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40

Liu, Danyang, Zhijian Zhou, and Hao Liu. "The Theoretical Total Synthesis of an Aromatic Esters of the Crinane Amaryllidaceae Alkaloid Ambelline." E3S Web of Conferences 267 (2021): 02011. http://dx.doi.org/10.1051/e3sconf/202126702011.

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ABSTRACT. A series of crinane-type alkaloid ambelline derivatives were assessed for their potency to inhibit both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE), which has been shown to be effective medicine for the treatment of Alzheimer’s disease. However, no enzyme modification has been reported total synthesis. In this work, two possible theoretical synthesis paths of Crinane-type alkaloid ambelline were discussed in this article. The major difficulty of the proposed synthesis was the synthesis of the quaternary carbon. One of the approaches emphasized on the reactions betwe

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41

Hellou, Jocelyne, Gervais Bérubé, Michael J. Newlands, Alex G. Fallis, and Eric J. Gabe. "Intramolecular Diels–Alder reactions of cyclopentadiene systems: Model studies for the total synthesis of the capnellenes." Canadian Journal of Chemistry 66, no. 3 (1988): 439–48. http://dx.doi.org/10.1139/v88-077.

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Model studies for a general intramolecular Diels–Alder approach to the tricyclo[6.3.0.02,6]undecene skeleton common to the capnellene marine sesquiterpenes are described. Suitably functionalized cyclopentadiene systems 14 and 21 were synthesized and their cycloaddition reactivity examined. Triene 14 cyclized to the tricyclic adducts 15 and 16. In contrast, the anticipated product 22 from intramolecular cycloaddition of triene 21 was not formed in isolatable yield. Instead the minor adduct (10% yield) possessed an exocyclic double bond and was assigned structure 30 based on its relative stabili

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42

Terzidis, Michael A., Eleni Dimitriadou, Constantinos A. Tsoleridis, and Julia Stephanidou-Stephanatou. "4-Picoline-catalyzed hetero-Diels–Alder type reactions: one-pot synthesis of pyrano[4,3-c]chromenes." Tetrahedron Letters 50, no. 19 (2009): 2174–76. http://dx.doi.org/10.1016/j.tetlet.2009.02.077.

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Kron, Kareesa J., Mikaela Kosich, Robert J. Cave, and David A. Vosburg. "Divergent Diels–Alder Reactions in the Biosynthesis and Synthesis of Endiandric-Type Tetracycles: A Computational Study." Journal of Organic Chemistry 83, no. 18 (2018): 10941–47. http://dx.doi.org/10.1021/acs.joc.8b01594.

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Ishihara, Kazuaki, Mayumi Miyata, Kouji Hattori, Toshiji Tada, and Hisashi Yamamoto. "A New Chiral BLA Promoter for Asymmetric Aza Diels-Alder and Aldol-Type Reactions of Imines." Journal of the American Chemical Society 116, no. 23 (1994): 10520–24. http://dx.doi.org/10.1021/ja00102a019.

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SHEA, K. J., K. S. ZANDI, A. J. STAAB, and R. CARR. "ChemInform Abstract: Disposable Tethers in Type 2 Intramolecular Diels-Alder Cycloaddition Reactions. Applications in Stereochemical Control." ChemInform 22, no. 39 (2010): no. http://dx.doi.org/10.1002/chin.199139134.

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Liu, Chengbin, Yanhong Tang, and Shuming Nie. "Synthesis and electronic properties of pentacene derivatives as promising n-type semiconductor candidates." Open Chemistry 4, no. 4 (2006): 723–31. http://dx.doi.org/10.2478/s11532-006-0036-y.

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AbstractTwo pentacene derivatives 1 and 2 were synthesized from the Diels-Alder reactions of furan derivatives with 1,4-benzoquinone. They were characterized by the methods of 1H — nuclear magnetic resonance spectroscopy (1H-NMR), matrix-assisted laser desorption/ionization time of flight mass spectrometry (MALDI-TOF MS), ultraviolet and visible spectrophotometry (UV-VIS), photoluminescence (PL) spectrometry and cyclic voltammetry (CV). The energy gaps of 1 and 2, taken directly from spectroscopic measurements, are broad as 2.72 and 2.46 eV, leading to blue and greenish blue photoluminescence,

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Yegorova, T., B. Barnych та Z. Voitenko. "REACTION OF PYRIDO[2,1-a]ISOINDOLE WITH З (R)- AND (S)- N-α-METHILBENZYLMALEIMIDE". Bulletin of Taras Shevchenko National University of Kyiv. Chemistry, № 1 (57) (2020): 44–47. http://dx.doi.org/10.17721/1728-2209.2020.1(57).11.

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Selective chemical reactions create new possibilities for controlled synthesis of compounds with pre-designed properties for further use in medical chemistry, material science and other fields. This is especially useful for such synthetic methodology as [4+2] cycloaddition. Current work is dedicated to study of reactions between N-chiral maleinimides with cyclic dienes based on the pyridoisoindol. Pyrido[2,1-a]isoindol turned out to be the most practical object to study the first example of asymmetric variant of the Diels-Alder reaction involving condensed isoindols. Previously, we established

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Keglevich, György. "Microwaves as “Co-Catalysts” or as Substitute for Catalysts in Organophosphorus Chemistry." Molecules 26, no. 4 (2021): 1196. http://dx.doi.org/10.3390/molecules26041196.

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The purpose of this review is to summarize the importance of microwave (MW) irradiation as a kind of catalyst in organophosphorus chemistry. Slow or reluctant reactions, such as the Diels-Alder cycloaddition or an inverse-Wittig type reaction, may be performed efficiently under MW irradiation. The direct esterification of phosphinic and phosphonic acids, which is practically impossible on conventional heating, may be realized under MW conditions. Ionic liquid additives may promote further esterifications. The opposite reaction, the hydrolysis of P-esters, has also relevance among the MW-assist

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Ishimaru, Kaori, Daiki Maeda, Kaori Ono, and Yuya Tanimura. "Mannich-Type Reactions of Aldimines and Hetero Diels-Alder Reactions of Aldehydes Catalyzed by Anion-Type Lewis Bases Derived from a Single Molecule." International Journal of Organic Chemistry 02, no. 03 (2012): 188–93. http://dx.doi.org/10.4236/ijoc.2012.23028.

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Kobayashi, S., M. Ueno, S. Saito, Y. Mizuki, H. Ishitani, and Y. Yamashita. "Asymmetric Catalysis Special Feature Part I: Air-stable, storable, and highly efficient chiral zirconium catalysts for enantioselective Mannich-type, aza Diels-Alder, aldol, and hetero Diels-Alder reactions." Proceedings of the National Academy of Sciences 101, no. 15 (2004): 5476–81. http://dx.doi.org/10.1073/pnas.0307870101.

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