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Synthesis 2003(18): 2763-2764
DOI: 10.1055/s-2003-44354
DOI: 10.1055/s-2003-44354
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
One-Pot Synthesis of 3-Substituted Isoxazoles from Phenyl Vinylic Selenide
Further Information
Received
13 August 2003
Publication Date:
25 November 2003 (online)
Publication History
Publication Date:
25 November 2003 (online)
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Abstract
Phenyl vinylic selenide was adopted for 1,3-dipolar cycloaddition to nitrile oxides and subsequent oxidation-elimination furnished 3-substituted isoxazoles with good yields in a one-pot, two-step transformation.
Key words
isoxazoles - phenyl vinylic selenide - 1,3-dipolar cycloaddition - oxidation-elimination
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1a
Dominguez E.Ibeus E.Matrinez de Margorta E.Palacious JK.San Marka E. J. Org. Chem. 1996, 61: 5435 -
1b
Buron C.Kairon LE.Hslu A. Tetrahedron Lett. 1997, 38: 8027 -
1c
Grunanger P.Vitafinzi P. Isoxazoles in the Chemistry of Heterocylic Compounds Vol. 1, Part I:Talyor EC. Wiley Interscience; New York: 1991. p.1-46 -
2a
Micetich RG. Can. J. Chem. 1970, 48: 467 -
2b
Wade P.Amin NV.Yen H.Price DT.Huhn GF. J. Org. Chem. 1984, 49: 4595 -
2c
Nunno LD.Scilimati A. Tetrahedron 1987, 43: 2181 -
2d
Cadogan JIG.Cameron DK.Gosney I.Tinley EJ.Wyse SJ.Amaro A. J. Chem. Soc., Perkin Trans. 1 1991, 2081 - 3
Samuilov YD.Soloveva SE.Konovalov AI.Mannafov TG. Zh. Org. Khim. 1979, 15: 243 -
4a
Kauffmann T.Ahlers H.Echsler K.-J.Schulz H.Tilhard H.-J. Chem. Ber. 1985, 118: 4496 -
4b
Pearson WH.Stevens EP. J. Org. Chem. 1998, 63: 9812 -
4c
Pearson WH.Szura DP.Postich MJ. J. Am. Chem. Soc. 1992, 114: 1329 -
4d
Pearson WH.Clark RB. Tetrahedron Lett. 1997, 38: 7669 -
5a
Reich HJ. Acc. Chem. Res. 1979, 12: 22 -
5b
Liotta D. Acc. Chem. Res. 1984, 17: 28 -
5c
Organoselenium Chemistry
Liotta D. Wiley; New York: 1987. -
5d
Back TG. The Chemistry of Organic Selenium and Tellurium Compounds Vol. 2:Patai S. Wiley; Chichester: 1987. Chap. 3. -
6a
Kataev EG.Mannafov TG.Remizov AB.Komarovskaya DA. J. Org. Chem. (USSR). 1975, 11: 2363 -
6b
Kataev EG.Mannafov TG.Berdnikov EA.Komarovskaya DA. J. Org. Chem. (USSR). 1973, 9: 1998 - 7
Comasseto JV. J. Organomet. Chem. 1983, 253: 131 - 8
Said SB.Skar J.ewski M J. Synth. Commun. 1992, 22: 1851ochowski - 9
Choji K.Katsumi T.Akira H. Heterocycles 1994, 37: 1075 - 10
Barber GN.Olofson RA. J. Org. Chem. 1978, 43: 3015 - 11
Bast K.Christl M.Huisgen R.Mack W.Sustmann R. Chem. Ber. 1973, 106: 3258 - 12
Maeda M.Kojima M. J. Chem. Soc., Perkin Trans. 1 1977, 239