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For recent paper in this area, see:
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For recent paper in this area, see:. Zhang W., Huang L., and Wang J. Synthesis (2006) 2053
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Synthesis
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61349188742
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2, AcOEt/cyclohexane (4:1)] and recrystallized from the indicated solvents to give the expected tricyclic product.
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2, AcOEt/cyclohexane (4:1)] and recrystallized from the indicated solvents to give the expected tricyclic product.
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21
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61349193589
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Selected data for 1,2,3,13b-tetrahydropyrrolo[1,2-d]dibenzo[b,f][1,4]oxazepin-3-one (4a, This compound was isolated as a white solid in 84% yield after recrystallization from Et2O and melted at 127 °C; IR (KBr) v 1711 cm-1; 1H-NMR (CDCl3) δ 2.22-2.44 (m, 1H, Hpyrrolidine, 2.47-2.71 (m, 3H, Hpyrrolidine, 5.28-5.39 (m, 1H, CH, 7.07-7.28 (m, 7H, Haromatic, 7.72 (d, 1H, J=8.3 Hz, Haromatic, 13C-NMR (CDCl3) δ 27.1 (CH2, 31.3 (CH2, 60.4 (CH, 121.8 (CH, 125.0 (CH, 125.1 (CH, 125.2 (CH, 126.6 (CH, 127.0 (CH, 127.6 (CH, 129.5 (CH, 130.4 (Cq, 130.9 (Cq, 151.6 (Cq, 155.7 (Cq, 174.1 (CO, MS (El, 70 ev) m/z: 251 (M, Anal. Calcd for C16H13NO2 251.28, C, 76.48; H, 5.21; N, 5.57. Found: C, 76.31; H, 5.09; N, 5.48
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2 (251.28): C, 76.48; H, 5.21; N, 5.57. Found: C, 76.31; H, 5.09; N, 5.48.
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22
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61349161507
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Selected data for 1,2-dihydropyrrolo[1,2-d]dibenzo[b,f][1,4]oxazepin-3-one (5a, This product was isolated as a white solid in 64% yield after recrystallization from Et2O/cyclohexane and melted at 115 °C; IR (KBr) v 1712 cm-1; 1H-NMR (CDCl3) δ 3.40 (s, 2H, CH2-C, 5.60 (s, 1H, CH{double bond, long}C, 7.13-7.42 (m, 6H, Haromatic, 7.52 (d, l H, J=7.6 Hz, Haromatic, 7.87 (d, I H, J=7.6 Hz, Haromatic, 13C-NMR (CDCl3) δ 37.5 (CH2, 102.3 (CH{double bond, long, 121.0 (CH, 121.8 (CH, 125.5 (CH, 125.6 (CH, 125.7 (CH, 127.0 (Cq, 127.3 (CH, 128.6 (CH, 129.0 (Cq, 131.2 (CH, 142.5 (Cq, 151.5 (Cq, 156.6 (Cq, 176.1 (CO, MS (EI, 70 ev) m/z: 249 (M, Anal. Calcd for C16H11NO2 249.27, C 77.10; H 4.45; N 5.62. Found: C 76.92; H 4.30; N 5.48
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2 (249.27): C 77.10; H 4.45; N 5.62. Found: C 76.92; H 4.30; N 5.48.
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23
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61349194837
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Selected data for 1-methyl-3,13b-dihydropyrrolo[1,2-d]dibenzo[b,f][1,4]oxazepin-3-one (6Ua, This product was isolated as a white solid in 65% yield after recrystallization from Et2O/hexane and melted at 159 °C; IR (KBr) v 1687 cm-1; 1H-NMR (CDCl3) δ 2.07 (d, 3H, J=1.3 Hz, CH3(CH, 6.11 (q, 1H, J=1.3 Hz, CH(CH3, 6.96-7.17 (q, 4H, Haromatic+CH{double bond, long}C, 7.20-7.35 (m, 4H, Haromatic, 8.85 (d, 1H, J=7.6 Hz, Haromatic, 13C-NMR (CDCl3) δ 11.6 (CH3, 60.7 (CH, 120.7 (CH, 121.3 (CH, 122.0 (CH, 125.0 (CH, 125.2 (CH, 125.3 (CH, 126.8 (CH, 129.5 (Cq, 130.6 (CH, 131.2 (Cq, 137.5 (CH, 137.7 (Cq, 146.1 (Cq, 156.6 (Cq, 169.9 (CO, MS (El, 70 ev) m/z: 263 (M, Anal. Calcd for C17H13NO2 263.29, C 77.55; H 4.98; N 5.32. Found: C 77.33; H 4.76; N 5.16
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2 (263.29): C 77.55; H 4.98; N 5.32. Found: C 77.33; H 4.76; N 5.16.
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