메뉴 건너뛰기




Volumn 50, Issue 14, 2009, Pages 1550-1553

Unexpected transformation of quinones to spirolactones and to naturally occurring naphthalenic compounds

Author keywords

[No Author keywords available]

Indexed keywords

LAPACHOL; NAPHTHALENE DERIVATIVE; NATURAL PRODUCT; NORDIHYDROLAPACHENONE; QUINONE DERIVATIVE; SPIRONOLACTONE; UNCLASSIFIED DRUG;

EID: 60249083657     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.01.058     Document Type: Article
Times cited : (8)

References (33)
  • 18
    • 60249101195 scopus 로고    scopus 로고
    • 1H and 13C NMR were recorded at room temperature using a Varian Gemini 200 (Varian, Palo Alto, CA, USA) in the solvents indicated, with TMS as internal standard. Chemical shifts (δ) are given in ppm and coupling constants (J) in Hertz. IR spectra were recorded using Perkin-Elmer and Nicolet IRFT. The mass spectra were obtained at 70 eV in a VG-autospec. The fragments were described as a relation between atomic mass units and the charge (m/z) and the relative abundance in percentage of the base peak intensity. General procedure for the synthesis of the spirolactones 4 and 5: 3 g of finely divided metallic copper, under strong agitation, was added to 1 mmol of the corresponding quinone dissolved in 10 mL of acetic acid. The reaction mixture was stirred at 60 °C for 20 h. After the end of the reaction was confirmed by TLC, the mixture was added to H2O and extracted with CH2Cl2 (3 × 50 mL) and washed several times with
    • 3).
  • 20
    • 37049120699 scopus 로고    scopus 로고
    • Burnett, A. R, Thomson, R. H. J. Chem. Soc. 1968, 850-853. Procedure for the synthesis of 2,2,2′,2′-tetramethyl-3,4,5,6,3′,4′-hexahydro-2H,2′H-[5,5′]bi[benzo[h]chromenyl]-6,6'-diol (6, To a solution of β-lapachone (1 mmol) in 10 mL of acetic acid was added 2.5 mL of HI under agitation. Soon after the mixture was refluxed for 2 h it was added to a solution of metabisulfite 2, The precipitate that was formed was filtered and washed with H2O distilled. The product was crystallized from benzene and was obtained as a white solid in 96% yield, mp 125 °C. λmax (EtOH) nm (log ε, 340, 331, 252, 211. MS [70 eV, m/z, 454(100, 398(30, 227(17, IR (KBr) cm-1: 3483, 2970, 2929, 2579, 1592, 1388, 765. 1H NMR (200 MHz, CDCl3) δ: 8.2-8.1 (4H, m, 7.6-7.4 (4H, m, 4.9 (2H, s, 2.5-2.2 (4H, m, 1.8 (4H, t, J, 7.0 Hz, 1.4 (12H, s, 13C NMR 50 MHz, CDCl3
    • 3) δ: 8.1-8.0 (2H, m), 7.5-7.4 (2H, m), 6.5 (1H, s), 2.8 (2H, t), 1.8 (2H, t), 1.4 (6H, s).
  • 24
    • 60249091291 scopus 로고    scopus 로고
    • note
    • 3).
  • 26
    • 60249098202 scopus 로고    scopus 로고
    • Enraf-Nonius COLLECT; Nonius BV: Delft, The Netherlands (1997-2000).
    • Enraf-Nonius COLLECT; Nonius BV: Delft, The Netherlands (1997-2000).
  • 27
    • 0031059866 scopus 로고    scopus 로고
    • Carter C.W., and Sweet R.M. (Eds), Academic Press, New York
    • Otwinowski Z., and Minor W. In: Carter C.W., and Sweet R.M. (Eds). Methods in Enzymology Vol. 276 (1997), Academic Press, New York 307-326
    • (1997) Methods in Enzymology , vol.276 , pp. 307-326
    • Otwinowski, Z.1    Minor, W.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.