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Journal articles on the topic 'Azadiene'

Author: Grafiati

Published: 9 March 2023

Last updated: 10 March 2023

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1

Malcolmson, Steven J., Kangnan Li, and Xinxin Shao. "2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines." Synlett 30, no. 11 (March 26, 2019): 1253–68. http://dx.doi.org/10.1055/s-0037-1611770.

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The development of new strategies for the preparation of chiral amines is an important objective in organic synthesis. In this Synpacts, we summarize our approach for catalytically accessing nucleophilic aminoalkyl metal species from 2-azadienes, and its application in generating a number of important but elusive chiral amine scaffolds. Reductive couplings with ketones and imines afford 1,2-amino tertiary alcohols and 1,2-diamines, respectively, whereas fluoroarylations of gem-difluoro-2-azadienes deliver α-trifluoromethylated benzylic amines.1 Introduction2 Background: Umpolung Strategies for Preparing Chiral Amines3 Background: 2-Azadienes4 Reductive Couplings of 2-Azadienes5 Fluoroarylations of gem-Difluoro-2-azadienes6 Summary and Outlook

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2

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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3

Dong, Xiao-Yan, and Da-Ming Du. "Asymmetric 1,4-Michael Addition Reaction of Azadienes with α-Thiocyanoindanones Catalyzed by Bifunctional Chiral Squaramide." Molecules 26, no. 17 (August 25, 2021): 5146. http://dx.doi.org/10.3390/molecules26175146.

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In this paper, the organocatalytic asymmetric 1,4-Michael addition reaction of azadienes and α-thiocyanoindanones was investigated. A series of chiral benzofuran compounds containing thiocyano group and quaternary carbon center were synthesized in moderate yields with good enantioselectivities (up to 90:10 er) and high diastereoselectivities (up to >95:5 dr). This is the first case of 1,4-Michael addition reaction using α-thiocyanoindanones to obtain a series of chiral thiocyano compounds and further broaden the scope of application of azadiene substrates. In addition, a possible reaction mechanism is also described in the article.

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4

Davis, Jeremy M., Richard J. Whitby, and Albert Jaxa-Chamiec. "1-Azadiene complexes of zirconocene." Journal of the Chemical Society, Chemical Communications, no. 24 (1991): 1743. http://dx.doi.org/10.1039/c39910001743.

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5

Barluenga, José. "Azadiene derivatives as synthetic intermediates." Bulletin des Sociétés Chimiques Belges 97, no. 8-9 (September 1, 2010): 545–72. http://dx.doi.org/10.1002/bscb.19880970801.

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6

Nakamura, Itaru, Takeru Jo, Dong Zhang, and Masahiro Terada. "N-Allenylnitrone acts as 2-azadiene in the Cu-catalyzed cascade reaction of O-propargylic oximes with azodicarboxylates." Org. Chem. Front. 1, no. 8 (2014): 914–18. http://dx.doi.org/10.1039/c4qo00156g.

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7

Zhang, Gaoting, Aimin Yu, Yingjie Lei, Xiangtai Meng, and Lei Zhang. "Synthesis of novel pyridinium 1,5-zwitterions and their reactivity with isatin-based α-(trifluoromethyl)imines: a sulfur-controlled domino reaction." Organic Chemistry Frontiers 8, no. 14 (2021): 3718–23. http://dx.doi.org/10.1039/d1qo00312g.

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A new stable pyridinium 1,5-zwitterion, generated from azadiene and 4-dimethylaminopyridine, was isolated. The reaction of pyridinium 1,5-zwitterion and isatin-derived α-(trifluoromethyl)imine was regulated by temperature.

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8

Bode, J., M. He, and J. Struble. "NHC-Catalyzed Azadiene Diels-Alder Reaction." Synfacts 2006, no. 8 (August 2006): 0840. http://dx.doi.org/10.1055/s-2006-942031.

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9

Cherkaoui, Hassan, Jacques Martelli, and René Grée. "Synthesis of new functionalized azadiene carbonyliron complexes." Tetrahedron Letters 35, no. 27 (July 1994): 4781–82. http://dx.doi.org/10.1016/s0040-4039(00)76966-8.

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10

DAVIS, J. M., R. J. WHITBY, and A. JAXA-CHAMIEC. "ChemInform Abstract: 1-Azadiene Complexes of Zirconocene." ChemInform 23, no. 18 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199218247.

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11

Zakharova, Valerija M., Anja Siegemund-Eilfelda, Joachim Sieler, and Bärbel Schulze. "Synthesis of N,N’-Linked Isothiazolium Salts via Intramolecular Cyclocondensation of Hydrazonium Salts." Zeitschrift für Naturforschung B 61, no. 4 (April 1, 2006): 464–70. http://dx.doi.org/10.1515/znb-2006-0413.

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Interaction of β -thiocyanatovinyl aldehydes with N-amino heterocycles leads to formation of α, β - unsaturated hydrazonium salts dependent on the functional surroundings. The latter can undergo further intramolecular cyclocondensation giving rise to N,N′-linked isothiazolium salts as the final product. The isolated hydrazonium salts, not undergoing ring formation, have s-trans conformation of the azadiene system

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12

Fell, Jason S., Blanton N. Martin, and K. N. Houk. "Origins of the Unfavorable Activation and Reaction Energies of 1-Azadiene Heterocycles Compared to 2-Azadiene Heterocycles in Diels–Alder Reactions." Journal of Organic Chemistry 82, no. 4 (February 9, 2017): 1912–19. http://dx.doi.org/10.1021/acs.joc.6b02524.

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13

CHERKAOUI, H., J. MARTELLI, and R. GREE. "ChemInform Abstract: Synthesis of New Functionalized Azadiene Carbonyliron Complexes." ChemInform 25, no. 47 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199447194.

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14

Adamovich, S. N., I. A. Ushakov, A. V. Afonin, N. V. Vchislo, E. N. Oborina, and D. V. Pavlov. "O- and S-containing 1-azadiene derivatives of 3-aminopropylsilatrane." Russian Chemical Bulletin 70, no. 2 (February 2021): 406–11. http://dx.doi.org/10.1007/s11172-021-3100-z.

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15

Shiraishi, Yasuhiro, Hajime Maehara, Katsutake Ishizumi, and Takayuki Hirai. "Hg(II)-Selective Excimer Emission of a Bisnaphthyl Azadiene Derivative." Organic Letters 9, no. 16 (August 2007): 3125–28. http://dx.doi.org/10.1021/ol0713133.

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16

Chaabene, Marwa, Abderrahim Khatyr, Michael Knorr, Moheddine Askri, Yoann Rousselin, and Marek M. Kubicki. "Crystal structure of 4,4-dibromo-1-(3,4-dimethoxyphenyl)-2-azabuta-1,3-diene-1-carbonitrile." Acta Crystallographica Section E Crystallographic Communications 72, no. 8 (July 22, 2016): 1167–70. http://dx.doi.org/10.1107/s2056989016011075.

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The title compound, C12H10Br2N2O2, represents an example of a planar π-conjugated 2-azabutadiene molecule, which is both an interesting starting material for further organic transformations and a potential ligand in organometallic coordination chemistry. Its metric molecular parameters are typical for the family of 2-azabuta-1,3-dienes not substituted at the (CH) 3-position. In the crystal, the almost planar (r.m.s. deviation = 0.0658 Å) azadiene molecules form one-dimensional double-wide ribbons through intermolecular halogen bonds (C—Br...O and C—Br...Br—C), which then stack in a slipped manner through weak C—H...Br and π–π interactions to generate a three-dimensional network.

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17

Aguilar, Enrique, Jesús Joglar, Isabel Merino, Bernardo Olano, Francisco Palacios, and Santos Fustero. "Stereoselective Syntheses of Allylic Amines Through Reduction of 1-Azadiene Intermediates." Tetrahedron 56, no. 41 (October 2000): 8179–87. http://dx.doi.org/10.1016/s0040-4020(00)00736-5.

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18

Rammash, Bahlul K., and John L. Wong. "Azadiene chemistry. 7. Selective substitutions of imidoyl halide in 2-azanorbornenes." Journal of Organic Chemistry 52, no. 1 (January 1987): 64–67. http://dx.doi.org/10.1021/jo00377a010.

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19

Sommer, Christian, Heinrich Nöth, Werner Ponikwar, and Wolfgang Beck. "Neue 3-Imidazolin-1-oxyl-Radikale mit pyridyl und chinolylhaltigen 4-(2-Aminovinyl)-Substituenten und Palladium, Platin und Ruthenium-Komplexe mit diesen 4-Amino-1-azadien-Liganden / New 3-Imidazoline-1-oxyl Radicals with Pyridyl and Quinolyl Containing 4-(2-Aminovinyl) Substituents and Palladium, Platinum and Ruthenium Complexes of these 4-Amino-1-aza-diene Ligands." Zeitschrift für Naturforschung B 59, no. 6 (June 1, 2004): 639–54. http://dx.doi.org/10.1515/znb-2004-0604.

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The addition of pyridyl and quinolyl nitriles to the 4-lithium salt of 1-hydroxy-2.2.4.5.5- pentamethyl-3-imidazoline with a silyl protected OH group affords 4-aminovinyl substituted imidazoline derivatives 3, 6, 9, 12, and 15 which can be converted into the corresponding nitroxide radicals 5, 8, 11, 14 and 17. The 4-amino-1-azadiene residues of these imidazoline nitroxides form a series of chelates of palladium (22 - 26, 29 - 32) and with ruthenium half sandwich complexes (33 - 36). Coordination of the pyridine or quinoline N atom has been observed in mononuclear (19 - 21) and trinuclear (27, 28) palladium complexes and the structure of 19 was determined by X-ray diffraction.

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20

Caballero, Antonio, Alberto Tárraga, Maria D. Velasco, and Pedro Molina. "Ferrocene–thiophene dyads with azadiene spacers: electrochemical, electronic and cation sensing properties." Dalton Trans., no. 11 (2006): 1390–98. http://dx.doi.org/10.1039/b508757k.

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21

He, Ming, Justin R. Struble, and Jeffrey W. Bode. "Highly Enantioselective Azadiene Diels−Alder Reactions Catalyzed by Chiral N-Heterocyclic Carbenes." Journal of the American Chemical Society 128, no. 26 (July 2006): 8418–20. http://dx.doi.org/10.1021/ja062707c.

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22

Rammash, Bahlul K., John F. Richardson, and John L. Wong. "Azadiene chemistry. 9. Regioselective hydrogenation and hydrodechlorination of a pentachloro-2-azanorbornene." Journal of Organic Chemistry 53, no. 18 (September 1988): 4241–44. http://dx.doi.org/10.1021/jo00253a015.

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23

Cuellar, Mauricio A., Luz K. Alegrı́a, Yolanda A. Prieto, Manuel J. Cortés, Ricardo A. Tapia, and Marcelo D. Preite. "Hetero-Diels–Alder reaction of halogenated quinones with a polygodial-derived azadiene." Tetrahedron Letters 43, no. 12 (March 2002): 2127–31. http://dx.doi.org/10.1016/s0040-4039(02)00246-0.

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24

Sugaya, Toru, Nobuyuki Kato, Shinji Tomioka, and Kentaro Tamaki. "Stereoselective Synthesis of Novel Thromboxane A2Receptor Antagonists via Stereoselective 1-Azadiene Isomerization." Chemistry Letters 19, no. 12 (December 1990): 2181–82. http://dx.doi.org/10.1246/cl.1990.2181.

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25

Boger, Dale L. "Heterocyclic and acyclic azadiene diels-alder reactions: Total synthesis of nothapodytine B." Journal of Heterocyclic Chemistry 35, no. 5 (September 1998): 1003–11. http://dx.doi.org/10.1002/jhet.5570350502.

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26

Surendranath, Yogesh, Kevin D. Welch, Bradley W. Nash, W. Hill Harman, William H. Myers, and W. Dean Harman. "Tungsten-Promoted Dearomatization of Heterocycles: Uncovering the Latent 2-Azadiene Character of Pyrimidines." Organometallics 25, no. 25 (December 2006): 5852–53. http://dx.doi.org/10.1021/om060960f.

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27

Zhou, Yi, Chao-Yun Zhu, Xu-Sheng Gao, Xue-Yan You, and Cheng Yao. "Hg2+-Selective Ratiometric and “Off−On” Chemosensor Based on the Azadiene−Pyrene Derivative." Organic Letters 12, no. 11 (June 4, 2010): 2566–69. http://dx.doi.org/10.1021/ol1007636.

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28

Rammash, B. K., J. L. Atwood, J. A. Weeks, and J. L. Wong. "Azadiene chemistry. Part 8. Polycyclic amines via novel [2 + 2] cycloaddition of imine." Journal of Organic Chemistry 52, no. 13 (June 1987): 2712–14. http://dx.doi.org/10.1021/jo00389a014.

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29

Aguilar, Enrique, Jesus Joglar, Isabel Merino, Bernardo Olano, Francisco Palacios, and Santos Fustero. "ChemInform Abstract: Stereoselective Syntheses of Allylic Amines Through Reduction of 1-Azadiene Intermediates." ChemInform 32, no. 7 (May 30, 2010): no. http://dx.doi.org/10.1002/chin.200107078.

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30

Zapata, Fabiola, Antonio Caballero, Arturo Espinosa, Alberto Tárraga, and Pedro Molina. "A Selective Chromogenic and Fluorescent Molecular Probe for YbIIIBased on a Bichromophoric Azadiene." European Journal of Inorganic Chemistry 2010, no. 5 (February 2010): 697–703. http://dx.doi.org/10.1002/ejic.200901001.

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31

Sergeev, Pavel G., Roman A. Novikov, and Yury V. Tomilov. "Lewis Acid-Catalyzed Formal (4+2)-Cycloaddition between Cross-Conjugated Azatrienes and Styrylmalonates: The Way to Functionalized Quinolizidine Precursors." Molecules 28, no. 1 (December 22, 2022): 88. http://dx.doi.org/10.3390/molecules28010088.

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Quinolizidine and azaphenalene alkaloids are common in nature and exhibit a pharmaceutical activity, which stirs up increased interest in expanding the range of methods for the synthesis of the corresponding derivatives. In this work, we attempted to adapt our previously presented method for the synthesis of tetrahydropyridines to the preparation of potential precursors for these heterocycles as a separate development of a necessary intermediate stage. To this end, we studied the reactions of β-styrylmalonates with N-protected cross-conjugated azatrienes in the presence of Sn(OTf)2. Moreover, the regioselectivity of the process involving unsymmetrically substituted azatrienes was estimated. The diene character of vinyltetrahydropyridines was studied in detail with the participation of PTAD. Finally, for the Ts-protected highly functionalized vinyltetrahydropyridines synthesized, a detosylation method to give new desired azadiene structures as precursors of the quinolizidine core was suggested.

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32

Barluenga, Jose´, Miguel Tomás, Alfredo Ballesteros, Javier Santamaría, Raúl Corzo-Suárez, and Santiago García-Granda. "Reaction of Fischer alkynylcarbene complexes with 1-azadiene derivatives: unexpected formation of 3,4-dihydropyridines." New Journal of Chemistry 25, no. 1 (2001): 8–10. http://dx.doi.org/10.1039/b005648k.

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33

Shiraishi, Yasuhiro, Hajime Maehara, and Takayuki Hirai. "Indole-azadiene conjugate as a colorimetric and fluorometric probe for selective fluoride ion sensing." Organic & Biomolecular Chemistry 7, no. 10 (2009): 2072. http://dx.doi.org/10.1039/b821466b.

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34

Sissouma, Drissa, Geoffroy Dequirez, Sylvain Collet, and André Guingant. "Preparation of a chiral azadiene for the synthesis of 5-aza analogues of angucyclinones." Tetrahedron Letters 52, no. 18 (May 2011): 2336–39. http://dx.doi.org/10.1016/j.tetlet.2011.02.084.

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35

Hong, Bor-Cherng, Jian-Lin Wu, Arun Kumar Gupta, Mahanandeesha Siddappa Hallur, and Ju-Hsiou Liao. "Azadiene Diels−Alder Cycloaddition of Fulvenes: A Facile Approach to the [1]Pyrindine System." Organic Letters 6, no. 20 (September 2004): 3453–56. http://dx.doi.org/10.1021/ol048762c.

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36

Boger, Dale L., and Qun Dang. "Synthesis of desacetamido P-3A: 1,3,5-triazine .fwdarw. pyrimidine heteroaromatic azadiene Diels-Alder reaction." Journal of Organic Chemistry 57, no. 6 (March 1992): 1631–33. http://dx.doi.org/10.1021/jo00032a001.

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37

Boger, Dale L. "Azadiene diels-alder reactions: Scope and applications. Total synthesis of natural andEnt-fredericamycin A." Journal of Heterocyclic Chemistry 33, no. 5 (September 1996): 1519–31. http://dx.doi.org/10.1002/jhet.5570330508.

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38

Cuellar, Mauricio A., Luz K. Alegria, Yolanda A. Prieto, Manuel J. Cortes, Ricardo A. Tapia, and Marcelo D. Preite. "ChemInform Abstract: Hetero-Diels-Alder Reaction of Halogenated Quinones with a Polygodial-Derived Azadiene." ChemInform 33, no. 27 (May 21, 2010): no. http://dx.doi.org/10.1002/chin.200227213.

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39

Boger, Dale L. "ChemInform Abstract: Heterocyclic and Acyclic Azadiene Diels-Alder Reactions: Total Synthesis of Nothapodytine B." ChemInform 30, no. 9 (June 17, 2010): no. http://dx.doi.org/10.1002/chin.199909298.

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40

Zhang, Shu, Qiang Xu, Jie Sun, and Jiabi Chen. "Remarkable Reactions of (η4-1-azadiene)Fe(CO)3Complexes with Aryllithium Reagents. Syntheses and Structures of Novel Chelated Furanyl-Coordinated Alkoxy(amino)carbeneiron, η4-Azadiene-Coordinated 17e Acyliron, and Iron Inner Salt Complexes." Organometallics 20, no. 11 (May 2001): 2387–99. http://dx.doi.org/10.1021/om010034v.

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41

Cuerva, Juan, and Antonio Echavarren. "Synthesis of Heterocyclic Quinones by Aza-Diels-Alder Reaction of a 4-Stannyl-1-azadiene." Synlett 1997, no. 2 (February 1997): 173–74. http://dx.doi.org/10.1055/s-1997-735.

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42

Bongini, Alessandro, Mauro Panunzio, Elisa Bandini, Giorgio Martelli, and Giuseppe Spunta. "Hetero Diels−Alder vs Electrocyclic Reaction of Azadiene: Selective Synthesis of All Stereoisomers of Threonines." Journal of Organic Chemistry 62, no. 25 (December 1997): 8911–13. http://dx.doi.org/10.1021/jo971395g.

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43

Motorina, Irina A., and David S. Grierson. "An intramolecular 1-azadiene Diels-Alder approach to the preparation of synthetic equivalents of pyridine." Tetrahedron Letters 40, no. 40 (October 1999): 7211–14. http://dx.doi.org/10.1016/s0040-4039(99)01463-x.

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44

Glinkerman, Christopher M., and Dale L. Boger. "Catalysis of Heterocyclic Azadiene Cycloaddition Reactions by Solvent Hydrogen Bonding: Concise Total Synthesis of Methoxatin." Journal of the American Chemical Society 138, no. 38 (September 14, 2016): 12408–13. http://dx.doi.org/10.1021/jacs.6b05438.

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45

Nebois, Pascal, Houda Fillion, Leila Benameur, Bernard Fenet, and Jean-Louis Luche. "Synthesis and NMR structural study of furoquinolines and naphthofurans from quinones and a 1-azadiene." Tetrahedron 49, no. 43 (January 1993): 9767–74. http://dx.doi.org/10.1016/s0040-4020(01)80179-4.

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46

SUGAYA, T., N. KATO, S. TOMIOKA, and T. TAMAKI. "ChemInform Abstract: Stereoselective Synthesis of Novel Thromboxane A2 Receptor Antagonists via Stereoselective 1-Azadiene Isomerization." ChemInform 23, no. 6 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199206215.

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47

Boger, Dale L., and Scott E. Wolkenberg. "Total Synthesis ofAmaryllidaceaeAlkaloids Utilizing Sequential Intramolecular Heterocyclic Azadiene Diels−Alder Reactions of an Unsymmetrical 1,2,4,5-Tetrazine." Journal of Organic Chemistry 65, no. 26 (December 2000): 9120–24. http://dx.doi.org/10.1021/jo0012546.

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48

Barluenga, Jose, Miguel Tomas, Alfredo Ballesteros, Javier Santamaria, Raul Corzo-Suarez, and Santiago Garcia-Granda. "ChemInform Abstract: Reaction of Fischer Alkynylcarbene Complexes with 1-Azadiene Derivatives: Unexpected Formation of 3,4-Dihydropyridines." ChemInform 32, no. 20 (May 15, 2001): no. http://dx.doi.org/10.1002/chin.200120111.

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49

Kosturko, George W., Peter M. Graham, William H. Myers, Timothy M. Smith, Michal Sabat, and W. Dean Harman. "Tungsten-Promoted Diels−Alder Cycloaddition of Pyridines: Dearomatization of 2,6-Dimethoxypyridine Generates a Potent 2-Azadiene Synthon." Organometallics 27, no. 17 (September 2008): 4513–22. http://dx.doi.org/10.1021/om800430p.

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50

Varaksin, M. V., E. V. Tretyakov, I. A. Utepova, G. V. Romanenko, A. S. Bogomyakov, D. V. Stass, R. Z. Sagdeev, V. I. Ovcharenko, and O. N. Chupakhin. "Synthesis of nitroxyl radical by direct nucleophilic functionalization of a C-H bond in the azadiene systems." Russian Chemical Bulletin 61, no. 7 (July 2012): 1469–73. http://dx.doi.org/10.1007/s11172-012-0190-7.

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