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

• Authors: Victor Rogachev , Victor Filimonov , Julya Kulmanakova , Mehman Yusubov , Wolfgang Bender
• 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

EN

Alkynes; isoxazoles; nitrates; sulfur trioxide

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2005
• Volume: 3
• Issue: 3
• Pages: 370-376

Dates

published

1 - 9 - 2005

online

1 - 9 - 2005

Contributors

author

Victor Rogachev

• Department of Organic Chemistry, Tomsk Polytechnic University, 634050, Tomsk, Russia

author

Victor Filimonov

• Department of Organic Chemistry, Tomsk Polytechnic University, 634050, Tomsk, Russia

author

Julya Kulmanakova

• Department of Chemistry, Siberian State Medical University, 634050, Tomsk, Russia

author

Mehman Yusubov

• Department of Chemistry, Siberian State Medical University, 634050, Tomsk, Russia

author

Wolfgang Bender

• 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]

Identifiers

DOI

10.2478/BF02479268