2290 J. Agric. Food Chem., Vol. 55, No. 6, 2007
Tian et al.
Scheme 1. General Synthetic Route for the Target Compound
1
Data for 6h: yield, 66%; mp 93.6-95.4 °C; H NMR (CDCl3), δ
Hz, Py-CH2), 4.66 (d, 1H, J ) 12.4 Hz, Ph-CH2), 4.65 (s, 1H, N-CH-
O), 4.55 (d, 1H, J ) 15.1 Hz, Ph-CH2), 4.53 (d, 1H, J ) 12.0 Hz,
Ph-CH2), 3.73-3.76 (m, 1H), 3.41-3.49 (m, 3H), 3.01-3.06 (m, 1H),
2.77-2.84 (m, 1H), 2.20-2.25 (m, 1H), 1.78-1.83 (m, 1H); IR (KBr,
cm-1) 3043, 1579, 1503, 1316, 1152, 1096; MS (EI, 1.30e4), m/z (%)
400 (M+, 3), 370 (35), 354 (11), 246 (27), 210 (11), 126 (25), 91 (100),
90 (6). HRMS: calcd for C20H21N4O3Cl (M+), 400.1302; found,
400.1325.
8.33 (d, J1 ) 2.3 Hz, 1H, Py-H), 7.92 (dd, J1 ) 2.4 Hz, J2 ) 8.2 Hz,
1H, Py-H), 7.33 (d, J2 ) 8.3 Hz, 1H, Py-H), 4.92 (d, 1H, J ) 15.4 Hz,
Py-CH2), 4.61 (d, 1H, J ) 15.5 Hz, Py-CH2), 4.58 (s, 1H, N-CH-O),
3.87-3.89 (m, 1H), 3.48-3.73 (m, 4H), 2.96-3.00 (m, 1H), 2.74-
2.79 (m, 1H), 2.06-2.09 (m, 1H), 1.78-1.83 (m, 1H), 1.47-1.57 (m,
2H), 1.17 (d, 3H, J ) 6.1 Hz, CHCH3), 0.90 (t, 3H, J ) 7.3 Hz, CH2-
CH3); IR (KBr, cm-1) 2972, 1573, 1560, 1513, 1460, 1328, 1175, 1056;
MS (EI, 2.71e4), m/z (%) 366 (M+, 7), 336 (100), 320 (27), 246 (30),
210 (17), 126 (100), 90 (8). HRMS: calcd for C16H21ClN4O3 (M+),
252.1302; found, 252.1303. HRMS: calcd for C17H23N4O3Cl (M+),
366.1459; found, 366.1465.
Data for 6n: yield, 76%; mp 155.8-158.0 °C; 1H NMR (CDCl3), δ
8.33 (d, J1 ) 2.7 Hz, 1H, Py-H), 8.32 (d, J3 ) 2.8 Hz, 1H, Py-H), 7.88
(dd, J1 ) 2.5 Hz, J2 ) 8.3 Hz, 1H, Py-H), 7.64 (dd, J3 ) 2.4 Hz, J4 )
8.2 Hz, 1H, Py-H), 7.36 (d, J2 ) 8.8 Hz, 1H, Py-H), 7.34 (d, J4 ) 9.0
Hz, 1H, Py-H), 4.98 (d, 1H, J ) 15.1 Hz, Py-CH2), 4.70 (t, 1H, J )
2.6 Hz, N-CH-O), 4.63 (d, 1H, J ) 12.1 Hz, Py-CH2), 4.55 (d, 1H,
J ) 12.0 Hz, Py-CH2), 4.54 (d, 1H, J ) 15.2 Hz, Py-CH2), 3.76-3.82
(m, 1H), 3.47-3.59 (m, 3H), 3.02-3.06 (m, 1H), 2.72-2.79 (m, 1H),
2.22-2.26 (m, 1H), 1.81-1.85 (m, 1H); IR (KBr, cm-1) 2979, 1570,
1553, 1474, 1334, 1275, 1216, 1082; MS (EI, 9.79e4), m/z (%) 435
(M+, 2), 275 (23), 142 (65), 126 (100), 114 (64), 90 (22), 78 (67).
HRMS: calcd for C19H19N5O3Cl2 (M+), 435.0865; found, 435.0888.
Data for 6i: yield, 68%; mp 118.8-120.8 °C; 1H NMR (CDCl3), δ
8.33 (d, J1 ) 2.1 Hz, 1H, Py-H), 7.92 (dd, J1 ) 2.3 Hz, J2 ) 8.3 Hz,
1H, Py-H), 7.34 (d, J2 ) 8.3 Hz, 1H, Py-H), 4.92 (d, 1H, J ) 15.1 Hz,
Py-CH2), 4.63 (d, 1H, J ) 15.1 Hz, Py-CH2), 4.52 (t, J ) 2.9 Hz, 1H,
N-CH-O), 3.84-3.90 (m, 1H), 3.48-3.60 (m, 3H), 3.22-3.29 (m,
2H), 2.98-3.03 (m, 1H), 2.70-2.77 (m, 1H), 2.13-2.17 (m, 1H), 1.78-
1.87 (m, 2H), 0.91 (d, 6H, J ) 6.7 Hz, CH(CH3)2); IR (KBr, cm-1
)
2989, 1573, 1533, 1348, 1288, 1169, 1016; MS (EI, 1.33e4), m/z (%)
366 (M+, 7), 336 (100), 320 (35), 246 (31), 210 (12), 126 (65), 90 (8).
HRMS: calcd for C17H23N4O3Cl (M+), 366.1459; found, 366.1458.
Data for 6j: yield, 51%; mp 132.4-133.9 °C; 1H NMR (CDCl3), δ
8.33 (d, J1 ) 1.6 Hz, 1H, Py-H), 7.93 (dd, J1 ) 1.8 Hz, J2 ) 8.2 Hz,
1H, Py-H), 7.34 (d, J2 ) 8.2 Hz, 1H, Py-H), 4.88 (d, 1H, J ) 15.0 Hz,
Py-CH2), 4.73 (s, 1H, N-CH-O), 4.62 (d, 1H, J ) 15.0 Hz, Py-CH2),
3.76-3.83 (m, 1H), 3.44-3.54 (m, 3H), 2.94-3.00 (m, 1H), 2.79-
2.86 (m, 1H), 1.95-1.99 (m, 1H), 1.86-1.92 (m, 1H), 1.25 (s, 9H,
CH(CH3)3); IR (KBr, cm-1) 2966, 1559, 1507, 1396, 1328, 1175, 1056;
MS (EI, 1.56e3), m/z (%) 366 (M+, 5), 336 (39), 320 (17), 246 (36),
210 (21), 126 (100), 90 (19). HRMS: calcd for C17H23N4O3Cl (M+),
366.1459; found, 366.1451.
1
Data for 6o: yield, 93%; mp 96.8-98.3 °C; H NMR (CDCl3), δ
8.33 (d, J1 ) 2.0 Hz, 1H, Py-H), 7.90 (dd, J1 ) 2.3 Hz, J2 ) 8.2 Hz,
1H, Py-H), 7.34 (d, J2 ) 8.2 Hz, 1H, Py-H), 4.98 (d, 1H, J ) 15.1 Hz,
Py-CH2), 4.86 (t, J ) 2.1 Hz, 1H, N-CH-O), 4.58 (d, 1H, J ) 15.1
Hz, Py-CH2), 4.19-4.29 (m, 2H), 3.89-3.95 (m, 1H), 3.57-3.64 (m,
2H), 3.47-3.53 (m, 1H), 3.00-3.05 (m, 1H), 2.69-2.75 (m, 1H), 2.50
(t, 1H, J ) 2.3 Hz), 2.18-2.22 (m, 1H), 1.80-1.84 (m, 1H); IR (KBr,
cm-1) 2919, 1573, 1507, 1454, 1431, 1338, 1154, 1062; MS (EI,
5.16e3), m/z (%) 348 (M+, 10), 318 (45), 302 (27), 246 (42), 210 (18),
126 (100), 90 (17). HRMS: calcd for C16H17N4O3Cl (M+), 348.0989;
found, 348.1012.
1
Data for 6p: yield, 91%; mp 97.8-100.3 °C; H NMR (CDCl3), δ
1
Data for 6k: yield, 49%; mp 81.5-87.2 °C; H NMR (CDCl3), δ
8.33 (d, J1 ) 2.2 Hz, 1H, Py-H), 7.91 (dd, J1 ) 2.4 Hz, J2 ) 8.2 Hz,
1H, Py-H), 7.34 (d, J2 ) 8.2 Hz, 1H, Py-H), 5.32 (t, J ) 6.3 Hz, 1H,
N-CH-O), 4.91 (d, 1H, J ) 15.1 Hz, Py-CH2), 4.60 (d, 1H, J ) 15.1
Hz, Py-CH2), 4.57-4.58 (m, 1H), 4.01-4.08 (m, 2H), 3.85-3.89 (m,
1H), 3.49-3.58 (m, 3H), 2.99-3.04 (m, 1H), 2.72-2.78 (m, 1H), 2.15-
2.19 (m, 1H), 1.79-1.81 (m, 1H), 1.77 (s, 3H, CH3), 1.69 (s, 3H, CH3);
IR (KBr, cm-1) 2934, 1572, 1508, 1467, 1316, 1175, 1187, 1067; MS
(EI, 2.04e3), m/z (%) 378 (M+, 6), 348 (33), 332 (12), 248 (100), 210
(26), 126 (95), 90 (21). HRMS: calcd for C18H23N4O3Cl (M+),
378.1459; found, 378.1432.
8.33 (d, J1 ) 1.9 Hz, 1H, Py-H), 7.92 (dd, J1 ) 2.1 Hz, J2 ) 8.2 Hz,
1H, Py-H), 7.34 (d, J2 ) 8.3 Hz, 1H, Py-H), 4.92 (d, 1H, J ) 15.0 Hz,
Py-CH2), 4.62 (d, 1H, J ) 14.9 Hz, Py-CH2), 4.53 (s, 1H, N-CH-O),
3.85-3.88 (m, 1H), 3.46-3.59 (m, 5H), 2.98-3.02 (m, 1H), 2.71-
2.77 (m, 1H), 2.13-2.17 (m, 1H), 1.77-1.82 (m, 1H), 1.57-1.59 (m,
2H, CH2), 1.31-1.33 (m, 4H, (CH2)2), 0.90 (t, 3H, J ) 6.6 Hz, CH3);
IR (KBr, cm-1) 2960, 1560, 1513, 1388, 1308, 1275; MS (EI, 8.67e3),
m/z (%) 380 (M+, 9), 350 (100), 334 (43), 246 (46), 128 (28), 126
(99), 43 (36). HRMS: calcd for C18H25N4O3Cl (M+), 380.1615; found,
380.1601.
Data for 6q: yield, 83%; mp 139.6-141.2 °C; 1H NMR (CDCl3), δ
8.32 (d, J1 ) 2.1 Hz, 1H, Py-H), 7.89 (dd, J1 ) 2.4 Hz, J2 ) 8.3 Hz,
1H, Py-H), 7.27-7.39 (m, 6H), 6.62 (d, 1H, J ) 15.9 Hz, Ph-CH2),
6.22-6.28 (m, 1H, PhsCH2dCH), 4.96 (d, 1H, J ) 15.1 Hz, Py-
CH2), 4.67 (t, 1H, J ) 2.7 Hz, N-CH-O), 4.57 (d, 1H, J ) 15.1 Hz,
Py-CH2), 4.26-4.30 (m, 1H, PhsCH2dCH-CH2), 4.12-4.22 (m, 1H,
PhsCH2dCH-CH2), 3.86-3.92 (m, 1H), 3.45-3.61 (m, 3H), 3.01-
3.06 (m, 1H), 2.76-2.83 (m, 1H), 2.19-2.24 (m, 1H), 1.78-1.85 (m,
1H); IR (KBr, cm-1) 2906, 1573, 1553, 1321, 1261, 1142; MS (EI,
1.16e4), m/z (%) 426 (M+, 2), 396 (10), 290 (10), 246 (12), 210 (5),
134 (17), 126 (23), 117 (100), 91 (23), 78 (10). HRMS: calcd for
C22H23N4O3Cl (M+), 426.1459; found, 426.1473.
1
Data for 6l: yield, 64%; mp 96.8-97.9 °C; H NMR (CDCl3), δ
8.33 (d, J1 ) 1.9 Hz, 1H, Py-H), 7.91 (dd, J1 ) 2.3 Hz, J2 ) 8.2 Hz,
1H, Py-H), 7.34 (d, J2 ) 8.2 Hz, 1H, Py-H), 4.92 (d, 1H, J ) 15.1 Hz,
Py-CH2), 4.62 (d, 1H, J ) 15.1 Hz, Py-CH2), 4.52 (t, J ) 1.5 Hz, 1H,
N-CH-O), 3.86-3.88 (m, 1H), 3.48-3.60 (m, 5H), 2.96-3.02 (m,
1H), 2.72-2.75 (m, 1H), 2.13-2.17 (m, 1H), 1.78-1.79 (m, 1H), 1.68-
1.71 (m, 1H), 1.45-1.49 (m, 2H), 0.90 (d, 6H, J ) 6.6 Hz, CH(CH3)2);
IR (KBr, cm-1) 2946, 1566, 1513, 1454, 1341, 1175, 1056; MS (EI,
1.01e4), m/z (%) 380 (M+, 10), 350 (100), 334 (37), 246 (43), 210
(15), 126 (72), 90 (9). HRMS: calcd for C18H25N4O3Cl (M+), 380.1615;
found, 380.1647.
1
1
Data for 6m: yield, 86%; mp 147.1-149.5 °C; H NMR (CDCl3),
Data for 6r: pale yellow liquid; yield, 66%; H NMR (CDCl3), δ
δ 8.31 (d, J1 ) 2.0 Hz, 1H, Py-H), 7.89 (dd, J1 ) 2.2 Hz, J2 ) 8.2 Hz,
1H, Py-H), 7.31-7.39 (m, 6H, Py-H, Ph-H), 4.94 (d, 1H, J ) 15.1
8.33 (s, 1H, Py-H), 7.91 (d, J ) 7.3 Hz, 1H, Py-H), 7.34 (d, J ) 8.2
Hz, 1H, Py-H), 4.92 (d, 1H, J ) 15.1 Hz, Py-CH2), 4.68 (s, 1H,