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Synlett
Volumn , Issue 2, 2009, Pages 263-267
An efficient approach to original substituted 2-arylidene-2H-[1,4]-oxazin- 3(4H)-ones via a tandem intramolecular P(O→C) migration/Horner-Wadsworth- Emmons olefination sequence
Author keywords

1,3 phosphorus migration; Arylidene; Horner Wadsworth Emmons olefination; Oxazine; Vinylphosphate
Indexed keywords

EID: 62349091173     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1087665     Document Type: Article
Times cited : (3)
References (43)
  • 25
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    • and references cited therein
    • Du, Y.; Wiemer, D. F. J. Org. Chem. 2002, 67, 5709; and references cited therein.
    • (2002) J. Org. Chem , vol.67 , pp. 5709
    • Du, Y.1    Wiemer, D.F.2
  • 27
    • 62349125841 scopus 로고    scopus 로고
    • α-Phosphonolactams analogous to 3 (Scheme 1) have been prepared previously, in a number of different ways, and used in olefination processes. For recent representative examples, see: (a) Gois, P. M. P.; Afonso, C. A. M. Eur. J. Org. Chem. 2003, 3798.
    • α-Phosphonolactams analogous to 3 (Scheme 1) have been prepared previously, in a number of different ways, and used in olefination processes. For recent representative examples, see: (a) Gois, P. M. P.; Afonso, C. A. M. Eur. J. Org. Chem. 2003, 3798.
  • 31
    • 62349104704 scopus 로고    scopus 로고
    • The 1,3-phosphorus migration reaction was easily followed by TLC. Synthesis of 4-(tert-Butoxycarbonyl)-2-(diphenoxyphosphoryl, 5-(diphenoxyphosphoryloxy)-3-oxo-2,3-dihydro-4H-[1,4]-oxazine (3) A solution of KHMDS (13.94 mL, 0.5 M in toluene, 6.97 mmol) in THF (20 mL) was cooled to -78°C under argon. Subsequently, a solution of 1 (0.500 g, 2.32 mmol, distilled diphenyl chlorophosphate (1.373 g, 5.11 mmol, and distilled HMPA (1.041 g, 5.81 mmol) in THF (15 mL) was added dropwise over 5 min. After 15 min at -78°C, KHMDS was added (4.65 mL, 2.32 mmol, After an additional hour at -78°C, the reaction mixture was diluted with Et 2O (85 mL, Water (125 mL) was then added, and the mixture was extracted with EtOAc. The organic phase was washed with brine, dried over anhyd MgSO4, and concentrated. Flash chromatography (PE-EtOAc, 7:3) afforded 3 0.315 g, 20, as a pale yellow oil; Rf, 0.5
    • +.
  • 32
    • 62349101750 scopus 로고    scopus 로고
    • 5c)
    • 5c)
  • 36
    • 62349092897 scopus 로고    scopus 로고
    • General Procedure for the Wiemer Rearrangement Followed by the Horner-Wadsworth-Emmons Reaction, Synthesis of (6Z)-4-(tert-Butoxycarbonyl)-6-(3,4,5-trimethoxybenzylidene)-5, 6-dihydro-5-oxo-4H-[1,4]-oxazin-3-yl Diphenyl Phosphate (4a) A solution of the bisvinylphosphate 25c (0.500 g, 0.74 mmol) in THF (7.5 mL) was cooled to -78°C under argon. Subsequently, n-BuLi (0.552 mL, 1.6 M in hexane, 0.88 mmol) was added dropwise, and the reaction mixture was stirred for 10 min at -78°C. A solution of 3,4,5- trimethoxybenzaldehyde (0.722 g, 3.68 mmol) in THF (2 mL, previously dried over MS 4 Å, was then added dropwise. After 15 min at -78°C and 150 min at 0°C, the reaction mixture was diluted with Et2O (10 mL, Water (10 mL) was then added, and the mixture was extracted with EtOAc. The organic phase was washed with brine, dried over anhyd MgSO4, and concentrated. Flash ch
    • +.
  • 38
    • 62349107619 scopus 로고    scopus 로고
    • General Procedure for Stille-Type Coupling Reactions, Synthesis of (2Z)-4-(tert-Butoxycarbonyl)-2-(3,4, 5-trimethoxybenzylidene)-5-{benzo[b][1,4]dioxin-2-yl}-2, 3-dihydro-3-oxo-[1,4]-oxazine (5a) To a stirred solution of enol phosphate 4a (0.517 g, 0.83 mmol) in THF (16 mL, benzo[b][1,4]dioxin-2-yl} tributylstannane (0.874 g, 2.07 mmol) and LiCl (0.105 g, 2.48 mmol) were added under argon. Then, the flask was evacuated and backfilled with argon three times. Under argon, Pd(PPh3)4 (0.096 g, 0.08 mmol) was added, and the mixture was heated at reflux during 150 min. After cooling, the reaction mixture was diluted with EtOAc. The organic phase was washed with brine, dried over anhyd MgSO4, and concentrated. Flash chromatography (PE-EtOAc, 9:1 then 8:2) afforded 5a (0.247 g, 59, as a yellow solid; mp 151-152°C. IR NaCl, 2978, 2942, 2836, 1759, 1702, 1493, 1246 cm -1
    • +: 287.11576; found: 287.1166.
  • 39
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    • Minireview: Soos, T. J.; Meijer, L.; Nelson, P. J. Drug News Perspect. 2006, 19, 325.
    • Minireview: Soos, T. J.; Meijer, L.; Nelson, P. J. Drug News Perspect. 2006, 19, 325.
  • 40
    • 62349104703 scopus 로고    scopus 로고
    • Kinase activities assay were performed as reported in ref. 15 and 17
    • 17.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.