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General Experimental Procedure. In a Schlenk tube, a mixture of nitroolefin (a or b, 0.10 mmol), nitrogen-containing aromatic or heteroaromatic compound (1-6, 13-15, 0.15 mmol) and catalyst (I and II, 0.01 mmol) in toluene (1 mL) or without solvent, was vigorously stirred at ambient temperature for the appropriate time (Table
[1]
or Table
[2]
). After completion of the reaction as indicated by 1H NMR, the reaction mixture was diluted with H2O and extracted with Et2O. The organic phases were combined, dried over Na2SO4 and concentrated under reduced pressure, and the crude mixture was purified by column chromatography. All the new compounds gave satisfactory analytical and spectral data. Typical data for representative compounds:
Analytical data of compound 10a: IR (CCl4): 3047, 2893, 1614, 1552, 1376, 1277, 895 cm-1. 1H NMR (300 MHz, CDCl3): δ = 1.05 (t, 3
J = 7.1 Hz, 6 H, 2 × CH
3CH2), 3.24 (c, 3
J = 7.2 Hz, 4 H, 2 × CH3CH
2), 4.71 (dd, 3
J = 8.8 Hz, 3
J = 7.5 Hz, 1 H, NO2CH2CH), 4.78-4.93 (m, 2 H, NO2CH2), 6.53 (d, 3
J = 8.7 Hz, 2 H, Ph), 6.97 (d, 3
J = 8.7 Hz, 2 H, Ph), 7.08-7.40 (m, 5 H, Ph). 13C NMR (400 MHz, CDCl3): δ = 12.48 (2 × CH3CH2), 44.25 (NO2CH2
CH), 48.21 (CH2NCH2), 79.66 (NO2CH2), 111.85 (CPh), 125.40 (Cq
Ph), 127.26, 127.50, 127.57, 140.03, 128.55, 128.86, (5 × CPh) 139.97, 147.01 (2 × Cq
Ph). MS (70 eV): m/z (%) = 298 [M+], 284 (17), 283 (86), 252 (50), 238 (100), 237 (19), 236 (56), 208 (28). HRMS: m/z calcd for C18H22N2O2: 298.1681; found: 298.1684.
Analytical data of compound 18b: IR (CCl4): 3061, 2860, 1555, 1468, 1426, 1377 cm-1. 1H NMR (400 MHz, CDCl3): δ = 0.83 (t, J = 7.1 Hz, 3 H, CH2CH
3), 1.12-1.36 (m, 6 H, 3 × CH2), 1.68-1.92 (m, 2 H, NO2CH2CHCH
2), 3.76 (s, 3 H, NCH3), 3.70-3.81 (m, 1 H, NO2CH2CH), 4.61 (dd, 2
J = 11.9 Hz, 3
J = 7.8 Hz, 1 H, NO2CHH), 4.66 (dd, 2
J = 11.9 Hz, 3
J = 7.4 Hz, 1 H, NO2CHH), 6.89 (s, 1 H, CH3NCH), 7.13 (t, 3
J = 7.8 Hz, 1 H, Ph), 7.25 (t, 3
J = 7.8 Hz, 1 H, Ph), 7.31 (d, 3
J = 8.2 Hz, 1 H, Ph), 7.61 (d, 3
J = 8.2 Hz, 1 H, Ph). 13C NMR (400 MHz, CDCl3): δ = 13.99 (CH2
CH3), 22.43, 26.88, 31.61, 32.49 (4 × CH2), 32.77 (NCH3), 36.29 (NO2CH2
CH), 80.72 (NO2CH2), 109.56 (CPh), 112.54 (Cq
Ph), 118.83, 119.20, 121.92 (3 × CPh), 126.55 (CH3NCHC), 126.64, 137.23 (2 × Cq
Ph). MS (70 eV): m/z (%) = 274 [M+], 228 (17), 214 (42), 171 (34), 158 (21), 157 (100), 156 (16). HRMS: m/z calcd for C16H22N2O2: 274.1681; found: 274.1687.
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