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Volumn 75, Issue 15, 2010, Pages 5289-5295

One-pot synthesis of aminoenone via direct reaction of the chloroalkyl enone with NaN 3: Rapid access to polycyclic alkaloids

Author keywords

[No Author keywords available]

Indexed keywords

DIRECT REACTIONS; ONE-POT PROCEDURES; ONE-POT SYNTHESIS; SODIUM AZIDE; SYNTHETIC ROUTES;

EID: 77955162140     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101226r     Document Type: Article
Times cited : (17)

References (41)
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    • Interestingly, acyclic enones gave different products under similar conditions, see
    • Interestingly, acyclic enones gave different products under similar conditions, see: Mahoney, J. M.; Smith, C. R.; Johnston, J. N. J. Am. Chem. Soc. 2005, 127, 1354-1355
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 1354-1355
    • Mahoney, J.M.1    Smith, C.R.2    Johnston, J.N.3
  • 24
    • 77955167061 scopus 로고    scopus 로고
    • Such 1,3-cycloaddition of alkylazide enone to triazoline was presumed in the literature, but chemists have never observed this intermediate up until the present moment
    • Such 1,3-cycloaddition of alkylazide enone to triazoline was presumed in the literature, but chemists have never observed this intermediate up until the present moment.
  • 25
    • 0000614865 scopus 로고
    • For the decomposition of nonpolarized triazoline, see
    • For the decomposition of nonpolarized triazoline, see: Wladkowski, B. D.; Smith, R. H.; Michejda, C. J. J. Am. Chem. Soc. 1991, 113, 7893-7897
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 7893-7897
    • Wladkowski, B.D.1    Smith, R.H.2    Michejda, C.J.3
  • 28
    • 39549110845 scopus 로고    scopus 로고
    • For the decomposition of polarized triazoline, see
    • For the decomposition of polarized triazoline, see: Hong, K. B.; Donahue, M. G.; Johnston, J. N. J. Am. Chem. Soc. 2008, 130, 2323-2328
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 2323-2328
    • Hong, K.B.1    Donahue, M.G.2    Johnston, J.N.3
  • 29
    • 77955152232 scopus 로고    scopus 로고
    • Initially, we thought that the migration attitude between the aryl group and acyl group would play an important role in the regioselectivity during this process
    • Initially, we thought that the migration attitude between the aryl group and acyl group would play an important role in the regioselectivity during this process.
  • 30
    • 77955164897 scopus 로고    scopus 로고
    • Interestingly, Molander et al. had observed (4h) that, treatment of the analogue of 7 in xylenes under reflux condition for 18-24 h gave enamides as sole products
    • Interestingly, Molander et al. had observed (4h) that, treatment of the analogue of 7 in xylenes under reflux condition for 18-24 h gave enamides as sole products.
  • 31
    • 77955162340 scopus 로고    scopus 로고
    • For the syntheses of substrates see the Supporting Information for details
    • For the syntheses of substrates see the Supporting Information for details.
  • 32
    • 84855639465 scopus 로고    scopus 로고
    • The crystallographic coordinates for 1 7 have been deposited with the Cambridge Crystallographic Data Centre; deposition no. 742901. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Rd., Cambridge CB2 1EZ, UK or via
    • The crystallographic coordinates for 1 7 have been deposited with the Cambridge Crystallographic Data Centre; deposition no. 742901. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Rd., Cambridge CB2 1EZ, UK or via www.ccdc.cam.ac.uk/data-request/cif.
  • 33
    • 33845554690 scopus 로고
    • 3 in a fridge at -6 °C after NMR experiment. The analogues of 14 were all treated with the same operation in this work, unfortunately no crystallines participated. The crystallographic coordinates for 14 have been deposited with the Cambridge Crystallographic Data Centre; deposition no. 742900. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Rd., Cambridge CB2 1EZ, UK or via; It should be noted that the earlier assigned structure of 14 is now demonstrated to be erroneous, see
    • 3 in a fridge at -6 °C after NMR experiment. The analogues of 14 were all treated with the same operation in this work, unfortunately no crystallines participated. The crystallographic coordinates for 14 have been deposited with the Cambridge Crystallographic Data Centre; deposition no. 742900. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Rd., Cambridge CB2 1EZ, UK or via www.ccdc.cam.ac.uk/data-request/cif; It should be noted that the earlier assigned structure of 14 is now demonstrated to be erroneous, see: Harding, T. T.; Mariano, P. S. J. Org. Chem. 1982, 47, 482-485
    • (1982) J. Org. Chem. , vol.47 , pp. 482-485
    • Harding, T.T.1    Mariano, P.S.2
  • 37
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    • De Mayo P. Part 2;, Ed.; Interscience: New York
    • Warnhoff, E. W In Molecular Rearrangements, Part 2; de Mayo, P., Ed.; Interscience: New York, 1964; pp 846 and 847
    • (1964) Molecular Rearrangements , pp. 846-847
    • Warnhoff, E.W.1
  • 38
    • 0000077697 scopus 로고
    • Manske R.H.F. Academic Press: London, UK For the synthesis of 1a, see
    • Boekelheide, V In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: London, UK, 1960; Vol. VII, pp 205. For the synthesis of 1a, see
    • (1960) The Alkaloids , vol.7 , pp. 205
    • Boekelheide, V.1
  • 41
    • 84855633581 scopus 로고    scopus 로고
    • 1H NMR spectra between their sample and ours in the aromatic area (6.58 vs 6.59, and 6.65 vs 6.81). For details, see ref 14e
    • 1H NMR spectra between their sample and ours in the aromatic area (6.58 vs 6.59, and 6.65 vs 6.81). For details, see ref 14e.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.