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Volumn 63, Issue 1, 2004, Pages 17-22

Synthesis of optically active tetrahydro-3-benzazepine-2-carboxylic acid derivatives via the ring expansion reaction of isoquinolines and enzymatic resolution

Author keywords

[No Author keywords available]

Indexed keywords

10B HYDROXYMETHYLOXAZOLOISOQUINOLINE; 3 BENZAZEPINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ISOQUINOLINE DERIVATIVE; TETRAHYDRO 3 BENZAZEPINE 2 CARBOXYLIC ACID; UNCLASSIFIED DRUG;

EID: 0346394080     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-03-9928     Document Type: Article
Times cited : (10)

References (40)
  • 2
    • 0042505129 scopus 로고
    • ed. by A. R. Katritzky, Academic Press, Inc., New York
    • (b) S. Kaspark, 'Advances in Heterocyclic Chemistry' Vol. 39, ed. by A. R. Katritzky, Academic Press, Inc., New York, 1986, p. 45.
    • (1986) Advances in Heterocyclic Chemistry , vol.39 , pp. 45
    • Kaspark, S.1
  • 15
    • 0035909641 scopus 로고    scopus 로고
    • The other examples of carboxylic acid or aldehyde derivatives, see: (a) J. R. Fuchs and R. L. Funk, Org. Lett., 2001, 3, 3349.
    • (2001) Org. Lett. , vol.3 , pp. 3349
    • Fuchs, J.R.1    Funk, R.L.2
  • 23
    • 0347379865 scopus 로고    scopus 로고
    • note
    • For reviews, see: Ref. 1a. For recent some references not included in the above review, see: Ref. 5b; and references cited therein.
  • 25
    • 0028150852 scopus 로고
    • and references cited therein
    • 4a,b were prepared as follows. Compound (4a): Treatment of propargyl 2-(3,4-dimethoxyphenyl)ethylcarbamate with LiN(TMS)2 (0.3 equiv.) in THF at 66 °C afforded 4a in 90% yield. Compound (4b): Treatment of 3-phenylprop-2-ynyl 2-(3,4-dimethoxyphenyl)ethylcarbamate with NaN(TMS)2 (0.3 equiv.) in the presence of 18-crown-6 (0.3 equiv.) in toluene at 60 °C afforded 4b in 97% yield. And also, see: Y. Tamaru, M. Kimura, S. Tanaka, S. Kure, and Z. Yoshida, Bull. Chem. Soc. Jpn., 1994, 67, 2838; and references cited therein.
    • (1994) Bull. Chem. Soc. Jpn. , vol.67 , pp. 2838
    • Tamaru, Y.1    Kimura, M.2    Tanaka, S.3    Kure, S.4    Yoshida, Z.5
  • 31
    • 0347379864 scopus 로고    scopus 로고
    • note
    • 3, followed by a conventional work-up. The residue was chromatographed (silica gel, hexane-AcOEt = 10: 1) to give 2a (9.9 g) in 85% yield.
  • 32
    • 0347379863 scopus 로고    scopus 로고
    • note
    • 5: C, 67.90; H, 6.78; N; 3.77. Found: C, 67.79; H, 6.78; N, 3.70.
  • 36
    • 0346749466 scopus 로고    scopus 로고
    • note
    • +) 386.1604, found 386.1601.
  • 37
    • 0346118872 scopus 로고    scopus 로고
    • note
    • 2O) δ: 31.38, 34.69, 45.49, 56.52, 56.58, 58.52, 113.9, 114.8, 129.4, 132.6, 147.4, 147.8, 171.5.
  • 38
    • 0347379855 scopus 로고    scopus 로고
    • note
    • 3, all diagrams and calculations were performed using maXus crystallographic software package, the refinement was performed using SHELX-97.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.