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Volumn 3, Issue 1, 2006, Pages 68-72

Utilization of a tandem Michael-Dieckmann reaction to synthesize orixalone A

Author keywords

4 hydroxy 2 quinolinones; Orixalone A; Tandem Michael Dieckmann reaction

Indexed keywords


EID: 34247220228     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017806774964378     Document Type: Article
Times cited : (5)

References (25)
  • 18
    • 0004198491 scopus 로고
    • For reviews on the tandem Michael-Dieckmann reaction see: a, Wiley: New York
    • For reviews on the tandem Michael-Dieckmann reaction see: (a) Ho, T.-L. Tandem Organic Reactions, Wiley: New York, 1992; pp. 89-94;
    • (1992) Tandem Organic Reactions , pp. 89-94
    • Ho, T.-L.1
  • 20
    • 34247211464 scopus 로고    scopus 로고
    • Preparation of 6 via a tandem Michael-Dieckmann reaction: To a solution of methyl N-methyl-2-(acryloylamino)benzoate (43.8 mg, 0.2 mmol) in THF (1 mL) under an atmosphere of argon at -78 °C was added phenyl magnesium chloride (0.200 mL; 2M in THF, After 1 h at -78 °C the solution was stirred at rt for 40 min and then 1 N HC1 (1 mL) was added. The reaction mixture was extracted with ethyl acetate. The organic extracts were combined, washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give a solid. The solid was washed with hexane/EtOAc (70:30) to give 6 (43 mg, 81% yield) as a white solid. 1H NMR (500 MHz, d6-DMSO, δ 3.58 (s, 3H, 3.98 (s, 2H, 7.10, 7.13 (m, 1H, 7.19, 7.26 (m, 5H, 7.46 (d, 1H, J=8.5 Hz, 7.59 (dt, 1H, J1=7.3 Hz, J2=1.5 Hz, 8.05 (dd, 1H, J1=7.5 Hz, J2=1 Hz, 13C NMR 100.5 MHz, d6-DMSO, δ 29.20, 29.46
    • +: 266.1171 (calculated: 266.1176).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.