Beilstein J. Org. Chem. 2014, 10, 848–857.
over anhydrous Na2SO4 and evaporated in vacuum to dryness
to obtain pure products. In the cases where precipitates did not
form, the solvents were evaporated to dryness under reduced
pressure. The residue was extracted by ethyl acetate (60 mL)
and washed with water (30 mL × 3). The organic layer was
dried over anhydrous Na2SO4 and evaporated in vacuum to
dryness. The purification of the crude product was achieved by
column chromatography (silica gel mesh size 230–240; eluent
50–100% EtOAc/hexane). Characterization data for one
representative compound from each series is presented here.
Supporting Information
Supporting Information File 1
Synthetic procedure and characterization data for all
compounds and crystallographic data for 1a, 1h, 2b and 3a.
Acknowledgements
We are grateful to Natural Sciences and Engineering Research
Council (NSERC) of Canada for financial support. TYC thanks
Nova Scotia Health Research Foundation (NSHRF) for granting
the Scotia Scholar Award.
5-(2-Oxopyrrolidin-1-yl)-6,6a-dihydroisoindolo[2,1-a]quinolin-
11(5H)-one (1a): Yield: 56%. White solid. mp: 225–227 °C;
1H NMR (CD3OD) δ 1.68–1.84 (m, 1H), 1.98–2.14 (m, 2H),
2.57–2.65 (m, 2H), 2.68–2.78 (m, 1H), 3.03–3.18 (m, 1H),
3.22–3.32 (m, 1H), 5.04 (d, J = 12.0 Hz, 1H), 5.73–5.75 (m,
1H), 7.10–7.25 (m, 2H), 7.32 (d, J = 6.6 Hz, 1H), 7.50–7.70 (m,
3H), 7.83 (d, J = 7.2 Hz, 1H), 8.45 (d, J = 8.1 Hz, 1H);
13C NMR (CD3OD) δ 18.9, 32.0, 32.2, 44.3, 50.0, 59.7, 121.5,
123.5, 124.7, 125.2, 125.7, 127.9, 129.3, 130.0, 133.0, 133.8,
137.8, 145.6, 167.8, 178.9; FTIR νmax (NaCl): 3051, 2953,
2921, 1689, 1490, 1456, 1380, 1282, 1213, 1094, 906, 759,
730 cm−1; HRMS m/z: [M + Na]+ calcd for C20H18N2O2Na,
341.1260; found, 341.1252.
References
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60.0, 121.7, 123.4, 124.8, 125.6, 126.5, 128.5, 129.1, 130.0,
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(E)-2-(2-Fluorophenyl)-3-(2-(2-oxopyrrolidin-1-yl)vinyl)isoin-
dolin-1-one (3a): Yield: 39%. Colorless solid, mp 260–262 °C;
1H NMR (CDCl3) δ 1.98–2.10 (m, 2H), 2.41–2.48 (m, 2H),
3.24–3.44 (m, 2H), 4.62 (dd, J = 9.6, 14.1 Hz, 1H), 5.55 (d,
J = 9.6 Hz, 1H), 7.12–7.33 (m, 4H), 7.40–7.47 (m, 1H), 7.57
(dt, J = 7.2, 26.4 Hz, 2H), 7.94 (d, J = 7.2 Hz, 1H); 13C NMR
(CDCl3) δ 17.5, 31.1, 45.2, 64.2, 107.5, 116.6, 116.9, 123.4,
124.4, 124.6, 125.0, 125.2, 128.9 (2C), 129.9, 131.7, 132.4,
145.8, 156.6, 159.9, 167.3, 173.3; FTIR νmax (NaCl): 3068,
2937, 1701, 1655, 1503, 1407, 1375, 1269, 758 cm−1; HRMS
m/z: [M + Na]+ calcd for C20H17FN2O2Na, 359.1166; found,
359.1149.
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856