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Volumn 1, Issue 4, 1999, Pages 673-676

Regiocontrolled synthesis of carbocycle-fused indoles via arylation of siyl enol ethers with o-nitrophenylphenyliodonium fluoride

Author keywords

[No Author keywords available]

Indexed keywords

2 NITROPHENYLPHENYLIODONIUM; 2-NITROPHENYLPHENYLIODONIUM; INDOLE DERIVATIVE; IODOBENZENE; NITROBENZENE DERIVATIVE;

EID: 0033606876     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990759j     Document Type: Article
Times cited : (91)

References (39)
  • 1
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    • The monoterpenoid indole alkaloids
    • part 4: Saxton J. E., Ed.; Wiley: Chichester
    • Recent reviews: (a) Herbert, R. B. The Monoterpenoid Indole Alkaloids, supplement to vol. 25, part 4 of The Chemistry of Heterocyclic Compounds: Saxton J. E., Ed.; Wiley: Chichester, 1994.
    • (1994) The Chemistry of Heterocyclic Compounds , vol.25 , Issue.SUPPL.
    • Herbert, R.B.1
  • 3
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    • Cordell, G. A., Ed.; Academic Press: New York, Chapter 9
    • (c) Saxton, J. E. In The Alkaloids: Cordell, G. A., Ed.; Academic Press: New York, 1998; Vol. 50, Chapter 9.
    • (1998) The Alkaloids , vol.50
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    • 0347225187 scopus 로고    scopus 로고
    • Cordell, G. A., Ed.; Academic Press: New York. Chapter 1
    • (d) Saxton, J. E. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York. 1998; Vol. 51, Chapter 1.
    • (1998) The Alkaloids , vol.51
    • Saxton, J.E.1
  • 7
    • 0003979828 scopus 로고    scopus 로고
    • Academic Press: San Diego, CA
    • (b) Sundberg, R. J. Indoles; Academic Press: San Diego, CA, 1996.
    • (1996) Indoles
    • Sundberg, R.J.1
  • 8
    • 0001426611 scopus 로고    scopus 로고
    • Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Science: Oxford
    • (c) Sundberg, R. J. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Science: Oxford, 1996; Vol. 2. pp 119-206.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.2 , pp. 119-206
    • Sundberg, R.J.1
  • 9
    • 0000119323 scopus 로고
    • Kreher, R., Ed.; Georg Thieme Verlag: Stuttgart, Hetarene I, and references therein
    • (d) Döpp, H.; Döpp, D.; Langer, U.; Gerding, B. In Methoden der Organischen Chemie; Kreher, R., Ed.; Georg Thieme Verlag: Stuttgart, 1994; Hetarene I, Teil 2, pp 546-1336, and references therein.
    • (1994) Methoden der Organischen Chemie , Issue.2 TEIL , pp. 546-1336
    • Döpp, H.1    Döpp, D.2    Langer, U.3    Gerding, B.4
  • 15
    • 0012114495 scopus 로고
    • Preparation of indoles via direct arylation of ketone enolates or their equivalents has been previously investigated. For example, see: (a) Kuehne, M. E. J. Am. Chem. Soc. 1962, 84, 837-847.
    • (1962) J. Am. Chem. Soc. , vol.84 , pp. 837-847
    • Kuehne, M.E.1
  • 19
    • 33751499126 scopus 로고
    • Phenylation of TMS enol ethers using diphenyl iodonium fluoride has been reported: Chen, K.; Koser, G. F. J. Org. Chem. 1991, 56, 5764-5767.
    • (1991) J. Org. Chem. , vol.56 , pp. 5764-5767
    • Chen, K.1    Koser, G.F.2
  • 28
    • 0042574911 scopus 로고    scopus 로고
    • note
    • 2O (30 mL) was added the iodonium iodide (3.6 g, 7.9 mmol), and the mixture was stirred for several hours. After removal of the insoluble material by filtration, the solution was concentrated below 30°C under reduced pressure (<5 Torr). The residue was diluted with 8 mL of MeCN and crystallized at 0°C to give NPIF (1, 1.80 g first crop, 0.33 g second crop; total 2.13 g, 78%).
  • 31
    • 0042073901 scopus 로고    scopus 로고
    • note
    • 13C NMR and IR spectra. See Supporting Information for the spectral data as well as copies of actual spectra.
  • 32
    • 0042574913 scopus 로고    scopus 로고
    • note
    • The modest yield for this example stands in contrast with the high yield obtained for the o-nitrophenylation of a complex intermediate leading to the natural product tabersonine (ref 5).
  • 33
    • 85088810207 scopus 로고    scopus 로고
    • note
    • 1H NMR) of cis-trans isomers.
  • 37
    • 0042574912 scopus 로고    scopus 로고
    • note
    • 3N) to give the indole product (4).


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