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Journal
2005 | 3 | 3 | 370-376
Article title

Simple synthesis of 3-acyl-5-alkyl(aryl)isoxazoles from terminal alkynes and nitrates of alkaline metals or ammonium

Content
Title variants
Languages of publication
EN
Abstracts
EN
A simple and general synthesis of 3-acyl-5-alkyl(aryl)isoxazoles by reaction of terminal alkynes with nitrates in acetic acid in the presence of SO3 or alkaline salts is described.
Keywords
Publisher

Journal
Year
Volume
3
Issue
3
Pages
370-376
Physical description
Dates
published
1 - 9 - 2005
online
1 - 9 - 2005
Contributors
  • Department of Organic Chemistry, Tomsk Polytechnic University, 634050, Tomsk, Russia
  • Department of Organic Chemistry, Tomsk Polytechnic University, 634050, Tomsk, Russia, filimonov@tpu.ru
  • Department of Chemistry, Siberian State Medical University, 634050, Tomsk, Russia
  • Department of Chemistry, Siberian State Medical University, 634050, Tomsk, Russia
  • Business Group Pharma, Research, Bayer AG, D-42096, Wuppertal, Germany
References
  • [1] V.O. Rogachev, M.S. Yusubov and V.D. Filimonov: “Reaction of phenylacetylene with sulfuric acid or sulfuric anhydride”, Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii), Vol. 35, (1999), pp. 415–418.
  • [2] V.O. Rogachev, M.S. Yusubov, V.D. Filimonov and V.D. Ogorodnikov: “Unexpected formation of (E)-1-(methylthio)-1,2-diphenyl-2-chloroethene in reaction of diphenylacetylene with DMSO in the presence of sulfur trioxide and CCl4”, Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii), Vol. 36, (2000), pp. 290–291.
  • [3] V.O. Rogachev, V.D. Filimonov and M.S. Yusubov: “A Novel Practical Reaction of Diarylalkyne With Sulfur Trioxide: Oxidation to 1,2-Diketones”, Synthesis, Vol. 7, (2001), pp. 1001–1003.
  • [4] V.O. Rogachev, V.D. Filimonov and M.S. Yusubov: “New reaction of terminal acetylenes with nitrates in the presence of sulfur trioxide: heterocyclization into 3-acyl-5-aryl(alkyl)isoxazoles”, Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii), Vol. 37, (2001), pp. 1192–1193. http://dx.doi.org/10.1023/A:1013169104293[Crossref]
  • [5] M.S. Yusubov, I.A. Perederina, V.D. Filimonov, T.-H. Park and K.-W. Chi: “A facile synthesis of α-iodo-β-nitroalkenes from alkynes using I2/NO3 or KI/NO3”, Synthetic Communications, Vol. 28, (1998), pp. 833–836. [Crossref]
  • [6] F. Gasparrini, M. Giovannoli, D. Misiti, G. Natile, G. Palmieri and L. Maresca: “Gold(III)-catalysed one-pot synthesis of isoxazoles from terminal alkynes and nitric acid”, Journal of American Chemical Society, Vol. 115, (1993), pp. 4401–4402. http://dx.doi.org/10.1021/ja00063a084[Crossref]
  • [7] K-i. Itoh, S. Takahashi, T. Ueki, T. Sugiyama, T.T. Takahashi and C.A. Horiuchi: “A novel one-pot synthesis of 3-acetyl- and 3-benzoylisoxazole derivatives using ammonium cerium nitrate (CAN)”, Tetrahedron Letters, Vol. 43, (2002), pp. 7035–7037. http://dx.doi.org/10.1016/S0040-4039(02)01612-X[Crossref]
  • [8] A. Quilico: “Acetylene and its isoxazole derivatives. XI. The structure of the reaction products of nitric acid with acetylene”, Gazzetta Chimica Italiana, Vol. 62, (1932), pp. 503–518.
  • [9] R. Warsinsky and E. Steckhan: “Oxidative free-radical additions of α-nitro ketones and α-nitro amides to alkenes and alkynes mediated by electrochemically regenerable manganese(III) acetate”, Journal of Chemical Society Perkin Trans. 1., Vol. 14, (1994), pp. 2027–2037. http://dx.doi.org/10.1039/p19940002027[Crossref]
  • [10] T.N. Duybova, O.I. Yurchenko, N.V. Grizai and N.V. Komarov: “Reactions of acetylenic hydrocarbons with dimedone and some o-nitro ketones”, Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii), Vol. 34, (1998), pp. 642–646.
  • [11] E. Cereda, A. Ezhaya, M. Quai and W. Barbaglia: “Solid-phase synthesis of 3-hydroxymethylisoxazoles via resin bound nitrile oxides”, Tetrahedron Letters, Vol. 42, (2001), pp. 4951–4953. http://dx.doi.org/10.1016/S0040-4039(01)00904-2[Crossref]
  • [12] V.D. Filimonov, Yu.Yu. Kulmanakova, M.S. Yusubov, I.A. Perederina, Ki-Whan Chi and O.Kh. Poleshchuk: “Halogenating and Nitrating Activity of Reagents Based on Sodium Nitrate and Alkali Metal Halides in Acetic Acid”, Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii), Vol. 40, (2004), pp. 917–923. http://dx.doi.org/10.1023/B:RUJO.0000045178.33131.c2[Crossref]
Document Type
Publication order reference
Identifiers
YADDA identifier
bwmeta1.element.-psjd-doi-10_2478_BF02479268
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