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Volumn 60, Issue 6, 1995, Pages 1484-1485

Benzenoid Ring Functionalization of Indoles and Tryptophols via Combined Directed Ortho Metalation—Cross Coupling Methodology

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; TRYPTOPHAN DERIVATIVE;

EID: 0028903040     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00111a003     Document Type: Article
Times cited : (43)

References (25)
  • 11
    • 0026611289 scopus 로고
    • For example, synthetic work has focused on the preparation of serotonin mimics exhibiting locked conformations or bearing additional functionality to probe receptor site selectivity
    • For example, synthetic work has focused on the preparation of serotonin mimics exhibiting locked conformations or bearing additional functionality to probe receptor site selectivity: Swain, C. J.; Baker, R.; Kneen, C.; Herbert, R.; Moseley, J.; Saunders, J.; Seward, E. M.; Stevenson, G. I.; Beer, M.; Stanton, J.; Watling, K.; Ball, R. G. J. Med. Chem. 1992, 35, 1019.
    • (1992) J. Med. Chem. , vol.35 , pp. 1019
    • Swain, C.J.1    Baker, R.2    Kneen, C.3    Herbert, R.4    Moseley, J.5    Saunders, J.6    Seward, E.M.7    Stevenson, G.I.8    Beer, M.9    Stanton, J.10    Watling, K.11    Ball, R.G.12
  • 12
    • 0025601765 scopus 로고
    • See also and references cited therein
    • See also: Varíe, D. L. Tetrahedron Lett. 1990, 31, 7583 and references cited therein.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 7583
    • Varíe, D.L.1
  • 16
    • 85022477173 scopus 로고
    • 2/DMF; 2. 10% Pd/C/toluene/H2, 1 atm and silylation (NaH/TBSCl) to afford the product in 63% overall yield without chromatography
    • 2/DMF; 2. 10% Pd/C/toluene/H2, 1 atm (Org. Synth. 1986, 63, 214) and silylation (NaH/TBSCl) to afford the product in 63% overall yield without chromatography.
    • (1986) Org. Synth. , vol.63 , pp. 214
  • 18
    • 0004571867 scopus 로고
    • Brossi, A., Ed.; Academic Press: New York
    • Ninomiya, I.; Kiguchi, T. The Alkaloids, Brossi, A., Ed.; Academic Press: New York, 1990; Vol. 38; p 1.
    • (1990) The Alkaloids , vol.38 , pp. 1
    • Ninomiya, I.1    Kiguchi, T.2
  • 19
    • 0001052366 scopus 로고
    • 4-Hydroxy- and 4-aminoindoles are structural components of psylocibin and teleocidin alkaloids; see and references cited therein
    • 4-Hydroxy- and 4-aminoindoles are structural components of psylocibin and teleocidin alkaloids; see: Nakatsuka, S.-I.; Masuda, T.; Asano, O.; Teramae, T.; Goto, T. Tetrahedron Lett. 1986, 27, 4327 and references cited therein.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 4327
    • Nakatsuka, S.-I.1    Masuda, T.2    Asano, O.3    Teramae, T.4    Goto, T.5
  • 23
    • 85010134011 scopus 로고
    • 3/DMEZreflux) on 4, E = Li, afforded the analogous cross-coupled product with loss of TBS in 19% yield. For other low yield couplings of pyridyl boron derivatives with 4-iodo- and 4-thallioindoles, see
    • 3/DMEZreflux) on 4, E = Li, afforded the analogous cross-coupled product with loss of TBS in 19% yield. For other low yield couplings of pyridyl boron derivatives with 4-iodo- and 4-thallioindoles, see: Somei, M.; Amari, H.; Makita, Y. Chem. Pharm. Bull. Jpn. 1986, 34, 3971.
    • (1986) Chem. Pharm. Bull. Jpn. , vol.34 , pp. 3971
    • Somei, M.1    Amari, H.2    Makita, Y.3
  • 25
    • 0042733411 scopus 로고
    • 2 to give 9a, 9b, and 9c, respectively. Inter alia, this may allow the preparation of 5-hy-droxytryptamine analogues. TBS (22) For a crystal structure of serotonin see
    • 2 to give 9a, 9b, and 9c, respectively. Inter alia, this may allow the preparation of 5-hy-droxytryptamine analogues. TBS (22) For a crystal structure of serotonin see: Bugg, C. E.; Thewalt U. Acta Crystallogr. Sect. B 1972, 28, 82.
    • (1972) Acta Crystallogr. Sect. B , vol.28 , pp. 82
    • Bugg, C.E.1    Thewalt, U.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.