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Volumn 52, Issue 37, 1996, Pages 12039-12048

The intramolecular Schmidt reaction of azides with tertiary alcohols: Synthesis of 5-(α-naphthyl)- and 5-(β-naphthyl)indolizidines as potential dopamine analogs and non-opiate antinociceptive agents

Author keywords

[No Author keywords available]

Indexed keywords

1,3,4,5',6,6',7,12B OCTAHYDRO 1',3' DIMETHYL 2H SPIRO[BENZO[B]FURO[2,3 A]QUINOLIZINE 2,4' PYRIMIDINE] 2' ONE; ALPHA 1 ADRENERGIC RECEPTOR; ALPHA 2 ADRENERGIC RECEPTOR; DOPAMINE 2 RECEPTOR; INDOLIZIDINE DERIVATIVE; PRAZOSIN; SPIPERONE;

EID: 0030576891     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00723-5     Document Type: Article
Times cited : (24)

References (36)
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    • (1983) Dopamine Receptors, ACS Symposium Series 224 , vol.224 , pp. 223-246
    • Kaiser, C.1
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    • 0011731443 scopus 로고
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    • (13) Kaiser, C. In Dopamine Receptor Agonists; G. Poste and S. T. Crooke, Ed.; Plenum Press: New York, 1984; pp 87-137.
    • (1984) Dopamine Receptor Agonists , pp. 87-137
    • Kaiser, C.1
  • 16
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    • (1989) Basic and Clinical Aspects of Neuroscience , vol.3 , pp. 47-55
    • Petcher, T.J.1
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    • note
    • (17) Högberg and coworkers have discussed the naphthalene-like receptor binding site which allows for binding of both butaclamol (3) and isobutaclamol (4). See ref. 15 and references cited therein.
  • 18
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    • U. S. Patent 3,919,230, 1975
    • (18) Hill and Lafferty have reported the synthesis of 4-substituted-1-(β-naphthylmethyl)piperazines that have anti-Parkinsonism activity. See: Hill, H. F.; Lafferty, J. J., U. S. Patent 3,919,230, 1975.
    • Hill, H.F.1    Lafferty, J.J.2
  • 23
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    • (23) For leading references for Aubé's work on Schmidt reactions of azides with carbonyl compounds, see: (a) Aubé, J.; Milligan, G. L. J. Am. Chem. Soc. 1991, 113, 8965-8966.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 8965-8966
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    • note
    • (29) Molecular modeling and comparison overlays were carried out using PCMODEL version 5.0-PPC.
  • 35
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    • note
    • (34) Hindered rotation about the bond between the indolizidine ring and the aromatic ring led to a complex NMR spectrum at room temperature, necessitating data aquisition at temperatures above the coalescence point.
  • 36
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    • (35) Prepared in 98% yield from 6-bromo-2-naphthol by treatment with NaH (1.1 equiv., THF, 0 °C, 1h) followed by MeI (2.0 equiv., 0 °C to room temperature). For a recent synthesis, see: Bernas, B. R.; Hossain, M. M. Eur. Polym. J. 1993, 29, 657-659.
    • (1993) Eur. Polym. J. , vol.29 , pp. 657-659
    • Bernas, B.R.1    Hossain, M.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.