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Synlett
Volumn , Issue 10, 2008, Pages 1475-1478
N-substituted tetronamides as ambident nucleophilic building blocks for the synthesis of new 4-aza-2,3-didehydropodophyllotoxins
Author keywords

Benzhydrylation; Copper; N arylation; Podophyllotoxin; Tetronamide
Indexed keywords

4 AZA 2,3 DIDEHYDROPODOPHYLLOTOXIN; AMIDE; COPPER; HETEROCYCLIC COMPOUND; PODOPHYLLOTOXIN DERIVATIVE;
EID: 46449125005     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078429     Document Type: Article
Times cited : (15)
References (57)
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    • Axelson, M.1    Larsson, O.2
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    • For previous use of TV-benzyl tetronamides as building block, see: a
    • For previous use of TV-benzyl tetronamides as building block, see: (a) Sydorenko, N.; Hsung, R. P.; Darwish, O. S.; Hahn, J. M.; Liu, J. J. Org. Chem. 2004, 69, 6732.
    • (2004) J. Org. Chem , vol.69 , pp. 6732
    • Sydorenko, N.1    Hsung, R.P.2    Darwish, O.S.3    Hahn, J.M.4    Liu, J.5
  • 45
    • 46449134480 scopus 로고    scopus 로고
    • Representative Experimental Procedure for Benzhydrylation Reaction: To a stirred solution of benzhydrol 6 (437 mg, 1.1 mmol, 1.1 equiv) and enamine 4a (189 mg, 1 mmol) in anhyd CH2Cl 2 (10 mL) under a N2 atmosphere at r.t. was added BF 3OEt2 (0.380 mL, 3 equiv, The mixture was stirred for 2 h before a sat. aq NaHCO3 solution (10 mL) was added. The aqueous layer was extracted with Et2O (3 x10 mL, The organic layers were washed with brine (5 mL, dried over MgSO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (cyclohexane-EtOAc, 7:3) to afford the alkylated product 8a as a white foam (455 mg, 80% yield, 1H NMR (400 MHz, CDCl3, δ, 3.74 (s, 6 H, 3.80 (s, 3 H, 4.05-4.16 (m, 2 H, 4.64-4.79 (d, AB system, J= 15.4 Hz, 2 H, 5.38 (s, 1 H, 5.93 (d, J= 1.3 Hz, 1 H, 6.00 d, J= 1.3 H
    • 81BrNa: 592.07692; found: 590.07755 and 592.07560.
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    • Beletskaya, 1. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.
    • (c) Beletskaya, 1. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.
  • 56
    • 46449118488 scopus 로고    scopus 로고
    • Representative Experimental Procedure for Intramolecular Copper-Mediated N-Arylation Reaction: To a solution of cyclization precursor 8a (217 mg, 0.38 mmol) in anhyd DMF (4 mL) at r.t. were added Cul (87 mg, 0.46 mmol, 1.2 equiv) and Cs2CO3 (311 mg, 0.96 mmol, 2.5 equiv, The resulting mixture was stirred at 90 °C for 16 h. A sat. aq NH4Cl solution (5 mL) was added and the aqueous phase was extracted with CH2Cl2 (3 x10 mL, The collected organic phases were washed with aq NH3-NH4C1 solution (1:1, 10 mL, brine (3 x5 mL, and dried over MgSO4. The solvent was removed under reduced pressure. The crude product was purified by flash chromatography (cyclohexane-EtOAc, 7:3) to afford aza-analogue 9a as a yellow foam (185 mg, quantitative yield, 1H NMR (400 MHz, CDCl3, δ, 3.82 (s, 9 H, 4.75-489 (m, 4 H, 5.08 (s, 1 H),5.89(d, J= 1.2 Hz, 1 H),5
    • 7NNa: 510.15232; found: 510.15154.
  • 57
    • 46449098820 scopus 로고    scopus 로고
    • The cyclization of enolic precursors such as 7 to give 4-oxa-2,3-didehydropodophyllotoxin analogues will be the object of a separate study and will be reported elsewhere.
    • The cyclization of enolic precursors such as 7 to give 4-oxa-2,3-didehydropodophyllotoxin analogues will be the object of a separate study and will be reported elsewhere.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.