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Unusual regioselectivity in [3+2] cycloaddition reactions between (E)-3-nitroacrylic acid derivatives and (Z)-C,N-diphenylimine N-oxide

Treść / Zawartość
Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
[3+2] cycloaddition reactions of -COOMe and -CN trans-substituted nitroethenes with (Z)-C,N-diphenylimine N-oxide were tested. For the contrast to most known nitroalkene/nitrone cycloaditions, the reactions studied realized with the formation of 5-nitroisoxazolidines.
Czasopismo
Rocznik
Strony
112--117
Opis fizyczny
Bibliogr. 15 poz., 1 il. kolor., 1 rys.
Twórcy
autor
  • Cracow University of Technology, Institute of Organic Chemistry and Technology, Cracow, Poland
  • Department of Organic Chemistry, Faculty of Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland
  • Cracow University of Technology, Institute of Organic Chemistry and Technology, Cracow, Poland
Bibliografia
  • [1] Romeo, R.; Navarra, M.; Giofrè, S.V.; Carnovale, C.; Cirmi, S.; Lanza, G.; Chiacchio, M.A.; Synthesis and biological activity of new arenediyne-linked isoxazolidines. Bioorg Med Chem. 2014, 22, 3379. DOI: 10.1016/j.bmc.2014.04.047
  • [2] Malhotra, S.; Balwani, S.; Dhawan, A.; Raunak; Kumar, Y.; Singh, B.K.; Olsen, C.E.; Prasad, A.K.; Parmar V.S.; Ghosh, B.; Design, synthesis and biological activity evaluation of regioisomeric spiro-(indoline-isoxazolidines) in the inhibition of TNF-α-induced ICAM-1 expression on human endothelial cells. Med Chem Commun. 2012, 3, 1536. DOI: 10.1039/c2md20216f
  • [3] Burton, G.; Clarke, G.J.; Douglas, J.D.; Eglington, A.J.; Frydrych, C.H.; Hinks, J.D.; Hird, N.W.; Novel C-2 Substituted Carbapenem Derivatives. Part II. Synthesis and Structure-activity Relationships of Isoxazolin-2-yl,Isoxazolidin-2-yl and 2-Pyrazolin-2-yl Carbapenems Generated Using 1,3-Dipolar Cycloaddition Chemistry. The Journal of Antibiotics. 1996, 49, 1266. DOI: 10.7164/antibiotics.49.1266
  • [4] Jasiński, R.; Mikulska, M.; Polewski, D.; Dresler, E.; [3+2] Cycloadditions of 1-halo-1-nitroethenes with (Z)-C-(3,4,5-trimethoxyphenyl)-N-methyl-nitrone as regio- and stereocontrolled source of novel bioactive compounds: preliminary studies. Current Chem Lett. 2016, in press. DOI: 10.5267/j.ccl.2016.2.001
  • [5] Ono, N.; The nitro group in organic synthesis. Wiley-VCH: Weinheim. 2001, 6, 159-181.
  • [6] Perekalin V.V., Lipina E.S., Berestovitskaya V.M., Efremov D.A.; Nitroalkenes: Conjugated Nitro Compounds. J.Wiley & Sons, Chichester. 1994.
  • [7] Siadati, S. A.; Rezazadeh, S. The extraordinary gravity of three atom 4π-components and 1,3-dienes to C20-nXn fullerenes; a new gate to the future of Nano technology. Sci. Radices. 2022, 1, 4, 46-68. DOI: 10.58332/v22i1a04
  • [8] Banerji, A.; Gupta, M.; Biswas, P. K.; Prangé, T.; Neuman, A.; 1,3-Dipolar Cycloadditions. Part XII - Selective Cycloaddition. Route to 4-Nitroisoxazolidine Ring Systems. Journal of Heterocyclic Chemistry. 2007, 44, 5, 1045 - 1049. DOI: 10.1002/jhet.5570440511
  • [9] Sridharan, V.; Muthusubramanian, S.; Sivasubramaniana, S.; Polborn, K.; Diastereoselective synthesis of 2,3,4,5-tetrasubstituted isoxazolidines via 1,3-dipolar cycloaddition. Tetrahedron 2004, 60, 8881-8892. DOI: 10.1016/j.tet.2004.07.021
  • [10] Jasiński, R.; Ziółkowska, M.; Demczuk, O.M.; Maziarka, A.; Regio- and Stereoselectivity of Polar [2+3] Cycloaddition Reactions between (Z)-C-(3,4,5-trimethoxyphenyl)-N-methylnitrone and Selected (E)-2-substituted Nitroethenes. Cent. Eur. J. Chem. 2014, 12, 586-593. DOI: 10.2478/s11532-014-0518-2
  • [12] Jasiński, R.; Mróz, K.; Kinetic aspects of [3+2] cycloaddition reactions between (E)-3,3,3-trichloro-1-nitroprop-1-ene and ketonitrones. Reac. Kinet. Cat. 2015, 116, 35-41. DOI: 10.1007/s11144-015-0882-8
  • [13] Szczepanek A., Jasińska E., Kącka A., Jasiński R.; An experimental and quantumchemical study of [2+3] cycloaddition between (Z)-C-(m,m,p-trimethoxyphenyl)-N-(p-methyphenyl)-nitrone and (E)-3,3,3-trichloro-1-nitroprop-1-ene: mechanistic aspects. Current Chemistry Letters, 2015, 4, 33-44. DOI: 10.5267/j.ccl.2014.10.003
  • [14] Shechter, H.; Conrad, F.; Daulton, A.; Kaplan, R.; Orientation in Reactions of Nitryl Chloride and Acrylic Systems. J. Am. Chem. Soc. 1952, 74, 3052. DOI: 10.1021/ja01132a029
  • [15] Jasiński, R.; Preparatyka alifatycznych nitrozwiązków, RTN: Radom. 2013, 3, 40.
  • [16] Bened, A.; Durand, R.; Pioch, D.; Geneste, P.; Guimon, C.; Guillouzo, G.P.; Declercq J-P.; Germain, G.; Briard, P.; Rambaud, J.; Roques, R.; Isoxazolidines by cycloadditions of N,α-Diphenyl Nitrone in the Benzo[b]thiophene S-Oxide and SS-Dioxide Series. J. Chem. Soc. Perkin Trans. 1984, 2, 1-6. DOI: 10.1039/P29840000001
Uwagi
W bibliografii brak poz. 11.
Opracowanie rekordu ze środków MNiSW, umowa nr SONP/SP/546092/2022 w ramach programu "Społeczna odpowiedzialność nauki" - moduł: Popularyzacja nauki i promocja sportu (2024).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-0b684795-e24e-4c70-9152-b79ce452b623
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