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Volumn 39, Issue 26, 1998, Pages 4595-4598

Synthesis of 3-methylindoles from N-aryl-N-(3- triisopropylsilylpropargyl)sulfonamides

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE ALKALOID; N ARYL N (3 TRIISOPROPYLSILYLPROPARGYL)SULFONAMIDE; SKATOLE; UNCLASSIFIED DRUG;

EID: 0032565925     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00847-8     Document Type: Article
Times cited : (22)

References (19)
  • 1
    • 0003540638 scopus 로고
    • Ed. Saxton, J, E. Interscience, New York
    • 1. "The Monoterpene Indole Alkaloids", Ed. Saxton, J, E. Interscience, New York, 1983.
    • (1983) The Monoterpene Indole Alkaloids
  • 3
    • 37049073783 scopus 로고
    • Recent developments in indole ring synthesis-methodology and applications
    • 3. Gribble, G. W. Recent developments in indole ring synthesis-methodology and applications. Contemporary Organic Synthesis, 1994, 1, 145-172.
    • (1994) Contemporary Organic Synthesis , vol.1 , pp. 145-172
    • Gribble, G.W.1
  • 4
    • 0001701652 scopus 로고
    • 4. Hyre, J. E.; Bader, A. R. J. Am. Chem. Soc. 1958, 80, 437-439. McDonald, B. G.; Proctor, G. R. J. Chem. Soc. Perkin I. 1975, 1446-1450.
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 437-439
    • Hyre, J.E.1    Bader, A.R.2
  • 7
    • 0000498692 scopus 로고
    • 6. Julian, P. L.; Meyer, E. W.; Magnani, A.; Cole, W. J. Am. Chem. Soc. 1945, 67, 1203-1211. Julian, P. L.; Meyer, E. W.; Printy, H. C. Heterocyclic Chemistry, ed. Elderfield, R. C, Wiley, New York, 1953. Vol 3, p. 32.
    • (1945) J. Am. Chem. Soc. , vol.67 , pp. 1203-1211
    • Julian, P.L.1    Meyer, E.W.2    Magnani, A.3    Cole, W.4
  • 8
    • 0000498692 scopus 로고
    • ed. Elderfield, R. C, Wiley, New York
    • 6. Julian, P. L.; Meyer, E. W.; Magnani, A.; Cole, W. J. Am. Chem. Soc. 1945, 67, 1203-1211. Julian, P. L.; Meyer, E. W.; Printy, H. C. Heterocyclic Chemistry, ed. Elderfield, R. C, Wiley, New York, 1953. Vol 3, p. 32.
    • (1953) Heterocyclic Chemistry , vol.3 , pp. 32
    • Julian, P.L.1    Meyer, E.W.2    Printy, H.C.3
  • 9
    • 0001463953 scopus 로고
    • 7. Sundberg, R. J.; Laurino, J. P. J. Org. Chem. 1984, 49, 249-254. For the use of acetals in the Nordlander modification of the Bischler indole synthesis see Nordlander, J. E.; Catalane, D. B.; Kotian, K. D.; Stevens, R. M.; Haky, J. E. J. Org. Chem. 1981, 46, 778-782.
    • (1984) J. Org. Chem. , vol.49 , pp. 249-254
    • Sundberg, R.J.1    Laurino, J.P.2
  • 10
    • 0001420375 scopus 로고
    • 7. Sundberg, R. J.; Laurino, J. P. J. Org. Chem. 1984, 49, 249-254. For the use of acetals in the Nordlander modification of the Bischler indole synthesis see Nordlander, J. E.; Catalane, D. B.; Kotian, K. D.; Stevens, R. M.; Haky, J. E. J. Org. Chem. 1981, 46, 778-782.
    • (1981) J. Org. Chem. , vol.46 , pp. 778-782
    • Nordlander, J.E.1    Catalane, D.B.2    Kotian, K.D.3    Stevens, R.M.4    Haky, J.E.5
  • 11
    • 37049174008 scopus 로고
    • 8. Kermack, W. O.; Perkin, W. H.; Robinson, R. J. Chem. Soc. 1921, 1602-1642. Fleming, I.; Woolias, M. J. Chem. Soc. Perkin I. 1979, 827-828. For a recent synthesis of 12 on a large scale see: Gan, T.; Liu, R.; Yu, P.; Zhao, S.; Cook, J. M. J. Org. Chem. 1997, 62, 9298-9304. Wieland, T.; Grimm, D. Chem. Ber. 1965, 98, 1727-1735.
    • (1921) J. Chem. Soc. , pp. 1602-1642
    • Kermack, W.O.1    Perkin, W.H.2    Robinson, R.3
  • 12
    • 37049094013 scopus 로고
    • 8. Kermack, W. O.; Perkin, W. H.; Robinson, R. J. Chem. Soc. 1921, 1602-1642. Fleming, I.; Woolias, M. J. Chem. Soc. Perkin I. 1979, 827-828. For a recent synthesis of 12 on a large scale see: Gan, T.; Liu, R.; Yu, P.; Zhao, S.; Cook, J. M. J. Org. Chem. 1997, 62, 9298-9304. Wieland, T.; Grimm, D. Chem. Ber. 1965, 98, 1727-1735.
    • (1979) J. Chem. Soc. Perkin I , pp. 827-828
    • Fleming, I.1    Woolias, M.2
  • 13
    • 0031436451 scopus 로고    scopus 로고
    • 8. Kermack, W. O.; Perkin, W. H.; Robinson, R. J. Chem. Soc. 1921, 1602-1642. Fleming, I.; Woolias, M. J. Chem. Soc. Perkin I. 1979, 827-828. For a recent synthesis of 12 on a large scale see: Gan, T.; Liu, R.; Yu, P.; Zhao, S.; Cook, J. M. J. Org. Chem. 1997, 62, 9298-9304. Wieland, T.; Grimm, D. Chem. Ber. 1965, 98, 1727-1735.
    • (1997) J. Org. Chem. , vol.62 , pp. 9298-9304
    • Gan, T.1    Liu, R.2    Yu, P.3    Zhao, S.4    Cook, J.M.5
  • 14
    • 0001301358 scopus 로고
    • 8. Kermack, W. O.; Perkin, W. H.; Robinson, R. J. Chem. Soc. 1921, 1602-1642. Fleming, I.; Woolias, M. J. Chem. Soc. Perkin I. 1979, 827-828. For a recent synthesis of 12 on a large scale see: Gan, T.; Liu, R.; Yu, P.; Zhao, S.; Cook, J. M. J. Org. Chem. 1997, 62, 9298-9304. Wieland, T.; Grimm, D. Chem. Ber. 1965, 98, 1727-1735.
    • (1965) Chem. Ber. , vol.98 , pp. 1727-1735
    • Wieland, T.1    Grimm, D.2
  • 15
    • 0029896223 scopus 로고    scopus 로고
    • 9. Black. D. St. C.; Kumar, N.; McConnell, D. B. Tetrahedron 1996, 52, 8925-8936. Black. D. St. C.; Rothnie, N. E.; Wong, L. C. H. Tetrahedron Lett. 1980, 21, 1883-1886. Black. D. St. C.; Rothnie, N. E.; Wong, L. C. H. Aust. J. Chem. 1983, 36, 2407-2412.
    • (1996) Tetrahedron , vol.52 , pp. 8925-8936
    • Black, D.St.C.1    Kumar, N.2    McConnell, D.B.3
  • 16
    • 0010502586 scopus 로고
    • 9. Black. D. St. C.; Kumar, N.; McConnell, D. B. Tetrahedron 1996, 52, 8925-8936. Black. D. St. C.; Rothnie, N. E.; Wong, L. C. H. Tetrahedron Lett. 1980, 21, 1883-1886. Black. D. St. C.; Rothnie, N. E.; Wong, L. C. H. Aust. J. Chem. 1983, 36, 2407-2412.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 1883-1886
    • Black, D.St.C.1    Rothnie, N.E.2    Wong, L.C.H.3
  • 17
    • 84943974456 scopus 로고
    • 9. Black. D. St. C.; Kumar, N.; McConnell, D. B. Tetrahedron 1996, 52, 8925-8936. Black. D. St. C.; Rothnie, N. E.; Wong, L. C. H. Tetrahedron Lett. 1980, 21, 1883-1886. Black. D. St. C.; Rothnie, N. E.; Wong, L. C. H. Aust. J. Chem. 1983, 36, 2407-2412.
    • (1983) Aust. J. Chem. , vol.36 , pp. 2407-2412
    • Black, D.St.C.1    Rothnie, N.E.2    Wong, L.C.H.3
  • 19
    • 0010421756 scopus 로고    scopus 로고
    • note
    • 11. Compounds 10, 14, 15, 18, 21, 23, 25-27 were made from the ArNHMs derivative by treatment with NaH/DMF/propargyl bromide, followed by LDA/THF/TIPSC1 at -78 °C.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.