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Volumn 5, Issue 1, 2008, Pages 38-41

First tetrakis-SRN1 reaction in naphthoquinone series

Author keywords

Anthracyclines; Electron transfer reaction; Naphthoquinone; Nitronate anions; Sulfones; Tetrakis SRN1

Indexed keywords


EID: 38949147874     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017808783330135     Document Type: Article
Times cited : (3)

References (17)
  • 9
    • 38949159635 scopus 로고    scopus 로고
    • 4 (246.26): C, 68.28; H, 5.73. Found: C, 68.21; H, 5.78.
    • 4 (246.26): C, 68.28; H, 5.73. Found: C, 68.21; H, 5.78.
  • 10
    • 38949092843 scopus 로고    scopus 로고
    • New derivatives: 4, orange solid, mp 125°C (methyl alcohol, 1H NMR (CDCl3) δ 2.10 (s, 6H, 2xCH3, 2.29 (s, 6H, 2xCH3, 3.81 (s, 6H, 2xOCH3, 13C NMR (CDCl3) δ 13.0 (2xCH3, 13.3 (2xCH3, 61.4 (2xOCH3, 123.5 (2xC, 140.4 (2xC, 142.9 (2xC, 154.3 (2xC, 184.9 (2xC=O, Anal. Calcd for C16H18O4 (274.31, C, 70.06; H, 6.61. Found: C, 70.47; H, 6.74. 5, yellow solid, mp 203°C (methyl alcohol, 1H NMR (CDCl3) δ 4.01 (s, 6H, 2xOCH3, 4.49 (s, 4H, 2xCH2Br, 4.76 (s, 4H, 2xCH2Br, 13C NMR (CDCl3) δ20.4 (2xCH2Br, 21.5 (2xCH2Br, 63.1 (2xOCH3) 123.5 (2xC, 140.8 (2xC, 142.8 (2xC, 155.3 (2xC, 181.0 (2xC=O, Anal. Calcd for C16H14Br4O4 589-90, C, 32.58; H, 2.39. Found
    • 4 (412.09): C, 46.63; H, 3.42. Found. C, 46.18; H, 3.43.
  • 12
    • 38949194166 scopus 로고    scopus 로고
    • New products: 7, yellow solid, mp 297°C (CCl4, 1H NMR (CDCl3) δ 2.01 (s, 6H, 2xCH3, 2.29 (s, 6H, 2xCH3, 7.57 (m, 6H, 8.09 (m, 4H, 13C NMR (CDCl3) δ12.9 (2xCH3, 13.6 (2xCH3, 122.4 (2xC, 128.7 (4xCH, 129.5 (2xC, 130.5 (4xCH, 133.7 (2XCH, 139.1 (2xC, 143.1 (2xC, 164.5 (2xC, 165.0 (2xC=O, 183.3 (2xC=O, Anal. Calcd for C28H22O6 (454.47, C, 74.00; H, 4.88. Found: C, 73.78; H, 4.89. 8, yellow solid, mp 233°C (ethyl alcohol, 1H NMR (CDCl3) δ 4.27-4.86 (m, 8H, 4xCH2Br, 7.61 (m, 6H, 8.29 (m, 4H, 13C NMR (CDCl3) δ 19.8 (2xCH2Br, 20.8 (2xCH2Br, 124.5 (2xC, 128.6 (2xC, 128.9 (4xCH, 130.6 (4xCH, 134.3 (2xCH, 139.0 (2xC, 143.5 (2xC, 146.5 (2xC, 164.2 (2xC=0, 179.9 2xC=0, Anal. Calcd for C28H18Br4O
    • +; characteristic tetrachloride isotop peaks are observed.
  • 13
    • 38949168065 scopus 로고    scopus 로고
    • General procedure for tetrakis-SRN1 reaction of 6 with nitroalkanes: Under nitrogen atmosphere, a solution of tetra-butylammonium hydroxide (40% in water, 2.9 mL, 3.84 mmol) was treated with nitroalkane (3.84 mmol) for 1 h. A solution of 2,3,6,7-tetrakis(chloromethyl)-5,8-dimethoxynaphthalene-1,4-dione 6(0.20 g, 0.48 mmol) in dichloromethane (20 mL) was added and the mixture was irradiated with a fluorescent lamps (2 × 60 W) for 10 min. at room temperature under an inert atmosphere. The organic layer was separated and the aqueous layer was extracted with dichloromethane (3 × 10 mL, The combined organic layers were washed twice with water 30 mL, dried over MgSO4 and removed under reduced pressure. Purification by chromatography on silica gel eluting with chloroform and recrystallization from methanol led to the corresponding product 10a-h
    • 4 and removed under reduced pressure. Purification by chromatography on silica gel eluting with chloroform and recrystallization from methanol led to the corresponding product 10a-h.
  • 14
    • 38949196336 scopus 로고    scopus 로고
    • New derivatives: 10a, orange solid, mp 207°C, 1H NMR (CDCl3) δ 1.54 (s, 12H, 4xCH3, 1.62 (s, 12H, 4xCH3, 3.28 (s, 4H, 2xCH2, 3.34 (s, 4H, 2xCH2, 3.74 (s, 6H, 2xOCH3, 13C NMR (CDCl3) δ26.1 (4xCH3, 26.7 (4xCH3, 36.4 (2xCH2, 37.0 (2xCH2, 62.0 (2xOCH3, 87.8 (2xCNO2, 88.5 (2xCNO2, 124.0 (2xC, 139.6 (2xC, 144.6 (2xC, 155.7 (2xC, 182.9 (2xC=O, Anal. Calcd for C28H38N4O12 (622.62, C, 54.01; H, 6.15; N, 9.00. Found: C, 54.09; H, 6,29; N, 9.05. 10b, orange so-lid, mp 132°C, 1H NMR.(CDCl3) δ 1.58-1.69 (m, 16H, 8xCH2, 1.79-1.90 (m, 8H, 4xCH2, 2.49-2.60 (m, 8H, 4xCH2, 3.32 (s, 4H, 2xCH2, 3.43 (s, 4H, 2xCH2, 3.75 s, 6H, 2xOCH3, 13C NMR
    • 12 (838.98): C, 62.99; H, 7.45; N, 6.68. Found: C, 62.43; H, 7.53; N, 6.70.
  • 15
    • 38949083115 scopus 로고    scopus 로고
    • General procedure for reaction of 6 with substituted sulfinate sodium salt. A solution of substituted sulfinate sodium salt (5.76 mmol) in dimethylsulfoxide (10 mL) was added dropwise to a solution of tetrachloride 6 (0.20 g, 0.48 mmol) in dimethylsulfoxide (6 mL) and stirred under inert atmosphere for 10 mm. The reaction mixture was poured into cold water and the precipitate was formed. After filtration, the crude product was recrystallized from methanol gave the corresponding tetrakis-S-alkylated product.
    • General procedure for reaction of 6 with substituted sulfinate sodium salt. A solution of substituted sulfinate sodium salt (5.76 mmol) in dimethylsulfoxide (10 mL) was added dropwise to a solution of tetrachloride 6 (0.20 g, 0.48 mmol) in dimethylsulfoxide (6 mL) and stirred under inert atmosphere for 10 mm. The reaction mixture was poured into cold water and the precipitate was formed. After filtration, the crude product was recrystallized from methanol gave the corresponding tetrakis-S-alkylated product.
  • 17
    • 38949197766 scopus 로고    scopus 로고
    • New derivatives: 10e, orange solid mp 266°C, 1H NMR (CDCl3) δ 3.62, s, 6H, 2xOCH3, 4.93 (a, 4H, 2xCH2SO2, 5.05 (a, 4H, 2xCH2SO2, 7.59-7.71 (m, 12H, 7.84 (m, 4H, 7.98 (m, 4H, 13C NMR (CDCl3) δ53.4 (2xCH2SO2, 54.2 (2xCH2SO2, 63.6 (2xOCH3, 125.0 (2xC, 128.0 (4xCH, 128.3 (4xCH, 129.5 (4xCH, 129.6 (4xCH, 132.8 (2XC, 134.4 (4xCH, 138.8 (4xC, 139.3 (2xC, 156.6 (2xC, 180.4 (2xC=O, Anal. Calcd for C40H34O12S4 (834.95, C, 57.54; H, 4.10. Found: C, 57.18; K 4.00. 10f, orange solid, mp 254°C, 1H NMR (CDCl3) δ 2.45 (s, 12M, 4xCH3, 3.63 (s, 6H, 2xOCH3, 4.89 (s, 4H, 2xCH2SO2, 5.01 (s, 4H, 2xCH2SO2, 7.39 (d, J, 8.2 Hz, 8H, 7.79 d, J, 8.2 Hz, 8H
    • 4 (754.99); C, 50.91; H, 6.68. Found: C, 50.99; H, 6.57.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.