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Volumn 11, Issue 5, 2009, Pages 1159-1162

Synthesis of 3-aminoisoxazoles via the addition-elimination of amines on 3-bromoisoxazolines

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BROMINATED HYDROCARBON; ISOXAZOLE DERIVATIVE;

EID: 64349120627     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9000284     Document Type: Article
Times cited : (28)

References (43)
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    • (b) Pinho e Melo, T. M. V. D. Curr. Org. Chem. 2005, 9, 925-958.
  • 19
    • 33746494445 scopus 로고    scopus 로고
    • This issue was also noted by others; see ref 6a. For a review of azoles cross-couplings, see: Schnürch, M, Flasik, R, Khan, A. F, Spina, M, Mihovilovic, M. D, Stanetty, P. Eur. J. Org. Chem. 2006, 2006, 3283-3307
    • This issue was also noted by others; see ref 6a. For a review of azoles cross-couplings, see: Schnürch, M.; Flasik, R.; Khan, A. F.; Spina, M.; Mihovilovic, M. D.; Stanetty, P. Eur. J. Org. Chem. 2006, 2006, 3283-3307.
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    • (c) Böshagen, H. Chem. Ber. 1967, 100, 3326-3330.
    • (1967) Chem. Ber , vol.100 , pp. 3326-3330
    • Böshagen, H.1
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    • 64349121831 scopus 로고    scopus 로고
    • For an example with an isoxazolo[4, 5-d]pyrimidine, see: Wagner, E.; Becan, L. Pol. J. Chem. 1995, 69, 70-73.
    • (d) For an example with an isoxazolo[4, 5-d]pyrimidine, see: Wagner, E.; Becan, L. Pol. J. Chem. 1995, 69, 70-73.
  • 24
    • 0037420808 scopus 로고    scopus 로고
    • For an example of the reaction of a 3-bromoisoxazoline with nucleobases, see
    • (a) For an example of the reaction of a 3-bromoisoxazoline with nucleobases, see: Coutouli-Argyropoulou, E.; Pilanidou, P. Tetrahedron Lett. 2003, 44, 3755-3758.
    • (2003) Tetrahedron Lett , vol.44 , pp. 3755-3758
    • Coutouli-Argyropoulou, E.1    Pilanidou, P.2
  • 25
    • 84973039763 scopus 로고
    • For an example using a phenylsulfonyl leaving group, see
    • (b) For an example using a phenylsulfonyl leaving group, see: Anderson, W. K.; Raju, N. Synth. Commun. 1989, 19, 2237-2242.
    • (1989) Synth. Commun , vol.19 , pp. 2237-2242
    • Anderson, W.K.1    Raju, N.2
  • 26
    • 64349097375 scopus 로고    scopus 로고
    • Rohm and Haas Company; Improved synthesis of haloformimine compounds
    • Dibromoformaldoxime is commercially available but is readily prepared; see: a, Eur. Pat. Appl. 979814, Feb. 16
    • Dibromoformaldoxime is commercially available but is readily prepared; see: (a) Berrier, J. V.; Umarvadia, A. S.; Rohm and Haas Company; Improved synthesis of haloformimine compounds. Eur. Pat. Appl. 979814, Feb. 16, 2000.
    • (2000)
    • Berrier, J.V.1    Umarvadia, A.S.2
  • 30
    • 77957810963 scopus 로고
    • For a general discussion of nitrile oxide cycloaddition with alkenes, see
    • (a) For a general discussion of nitrile oxide cycloaddition with alkenes, see: Easton, C. J.; Hughes, C. M. M.; Savage, G. P.; Simpson, G W. Adv. Heterocycl. Chem. 1994, 60, 261-327.
    • (1994) Adv. Heterocycl. Chem , vol.60 , pp. 261-327
    • Easton, C.J.1    Hughes, C.M.M.2    Savage, G.P.3    Simpson, G.W.4
  • 35
    • 64349090916 scopus 로고    scopus 로고
    • See Supporting Information for the synthesis of the 3-bromoisoxazoline substrates
    • See Supporting Information for the synthesis of the 3-bromoisoxazoline substrates.
  • 36
    • 64349100033 scopus 로고    scopus 로고
    • The reaction was performed at 80 °C (DIPEA, EtOH, oil bath) for various substrates and the conversions were determined by HPLC after 18 h.. Reaction rates are in the order 6j > 6f > 6d > 6e - 6c > 6a
    • The reaction was performed at 80 °C (DIPEA, EtOH, oil bath) for various substrates and the conversions were determined by HPLC after 18 h.. Reaction rates are in the order 6j > 6f > 6d > 6e - 6c > 6a
  • 37
    • 64349107957 scopus 로고    scopus 로고
    • This is consistent with the fact that we did not observe the addition-elimination of the solvent n-butanol on 3-bromoisoxazolines 6d when sodium carbonate was used as a base. The 3-butoxyisoxazoline 10 was obtained upon replacement of Na2CO3 with K3PO4. See Supporting Information
    • 4. See Supporting Information.
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    • For the use of NBS, see
    • (a) For the use of NBS, see: Bianchi, G.; Grünanger, P. Tetrahedron 1965, 21, 817-822.
    • (1965) Tetrahedron , vol.21 , pp. 817-822
    • Bianchi, G.1    Grünanger, P.2
  • 42
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    • For the use of iodine in DMSO to oxidize 3, 5-diarylisoxazolines, see: Deshmukh, A. Y.; Raghuwanshi, P. B.; Doshi, A. G. Asian J. Chem. 2002, 14, 548-550.
    • For the use of iodine in DMSO to oxidize 3, 5-diarylisoxazolines, see: Deshmukh, A. Y.; Raghuwanshi, P. B.; Doshi, A. G. Asian J. Chem. 2002, 14, 548-550.
  • 43
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    • See Supporting Information for the effect of various inorganic and organic bases on the oxidation of 8d by iodine
    • See Supporting Information for the effect of various inorganic and organic bases on the oxidation of 8d by iodine.


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