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Volumn , Issue 15, 2007, Pages 2363-2366

Application of the hypervalent iodine reagent to the synthesis of some pentasubstituted aporphine alkaloids

Author keywords

1 benzyltetrahydroisoquinoline; Aporphine; Hypervalent iodine; Neospirinedienone; p p coupling

Indexed keywords

1 BENZYLTETRAHYDOISOQUINOLINE; APORPHINE DERIVATIVE; IODINE DERIVATIVE; MORPHINANDIENONE; NEOSPIRINEDIENONE; PHENYLIODINE BIS(TRIFLUOROACETATE); REAGENT; UNCLASSIFIED DRUG;

EID: 34948839846     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-985596     Document Type: Article
Times cited : (13)

References (40)
  • 6
    • 77957029013 scopus 로고
    • Brossi, A, Ed, Academic Press: New York
    • Kametani, T.; Honda, T. In The Alkaloids, Vol. 24; Brossi, A., Ed.; Academic Press: New York, 1985, 153.
    • (1985) The Alkaloids , vol.24 , pp. 153
    • Kametani, T.1    Honda, T.2
  • 35
    • 34848929190 scopus 로고    scopus 로고
    • Typical Procedure: To a stirred solution of N-formyltetrahydroisoquinoline 2g (150 mg, 0.40 mmol) in CH 2Cl2 (10 mL) was added a solution of bis(trifluoroacetoxy) iodobenzene (191 mg, 0.44 mmol) and BF3·OEt2 (0.12 mL, 0.88 mmol) in CH2Cl2 (5 mL) at -40°C under an argon atmosphere. The reaction mixture was stirred at -40°C for 1 h, then sat. NaHCO3 (30 mL) was added followed by extraction with CH 2Cl2 (3 x 30 mL, The combined CH2Cl 2 extracts were dried over anhyd Na2SO4 and evaporated to dryness in vacuo. The crude product was purified by PLC on silica gel using 50% EtOAc-hexane as a developing solvent to give aporphine 1g (62 mg, 42, Recrystallization from EtOAc afforded yellow needles; mp 193.0-193.6°C. IR (nujol, 1675, 1602, 1570, 1520 cm-1. 1H NMR 300 MHz, CDCl3
    • +, 327 (50.32), 297 (100.00).
  • 39
    • 0017809090 scopus 로고
    • For a related migration involving stereoelectronic factors, see
    • (b) For a related migration involving stereoelectronic factors, see: Evan, D. A.; Hart, D. J.; Koelsch, P. M. J. Am. Chem. Soc. 1978, 100, 4593.
    • (1978) J. Am. Chem. Soc , vol.100 , pp. 4593
    • Evan, D.A.1    Hart, D.J.2    Koelsch, P.M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.