Evaluation Only. Created with Aspose.PDF. Copyright 2002-2021 Aspose Pty Ltd.
7772 Wu et al.
Asian J. Chem.
CH3OH). IR (KBr, νmax, cm-1): 3488 (νO-H), 3416 (fermi
resonance of 2 δN-H and νas N-H), 3294, 3165 (νN-H, NH2), 1627
(νC=N), 1610 (δN-H, NH2), 1556, 1514 (νC=C, C6H4-), 1380 (νC-O),
1279 (νC-C), 1230 (νC-N), 842, 800 (δC-H, C6H4-); 1H NMR (300
MHz, DMSO) δ (ppm): 0.68 (s, 3H, 10-CH3), 1.23 (d, J = 8.6
Hz, 1H, 6-CH), 1.35 (s, 3H, 11-CH3), 2.30 (t, J = 2.6 Hz, 1H,
8-CH), 2.50-2.64 (m, 2H, 9-CH2), 2.71-2.88 (m, 2H, 5-CH2),
6.19 (s, 2H, NH2), 6.83 (d, J = 8.6 Hz, 2H, 3', 5'-CH), 7.57 (d,
J = 8.6 Hz, 2H, 2', 6'-CH), 9.67 (s, 1H, Ar-OH); 13C NMR
(300 MHz, DMSO) δ (ppm): 21.54, 26.11, 29.82, 29.89, 38.61,
40.87, 50.07, 111.82, 115.20, 129.92, 130.51, 158.41, 161.76,
162.65, 175.56; MS m/z (% relative intensity): 281 (M+, 75),
280 (68), 266 (40), 252 (14), 239 (40), 238 (53), 225 (17),
213 (26), 172 (4), 147 (9), 131 (7), 119 (100), 91 (8), 77 (17),
65 (10), 51 (4);Anal. Calcd for C17H19N3O: C, 72.56; N, 14.94;
H, 6.82. Found: C, 72.53; N, 14.90; H, 6.89.
Synthesis of compound 3f: A mixture of 2f (1.36 g, 5
mmol), guanidine hydrochloride (0.95 g, 10 mmol), potassium
tert-butoxide (2.24 g, 20 mmol), methylbenzene (30 mL) and
ethanol (5 mL) was refluxed for 4 h, other conditions reference
3a. colourless transparent crystal; yield = 66.2 %; purity of
99.3 %; m.p. 223.7-224.4 °C; [α]D20 = -59.0° (c = 0.1, CH3OH).
IR (KBr, νmax, cm-1): 3385 (νO-H), 3311, 3172 (νN-H, NH2), 1699
(νC=N), 1639 (δN-H, NH2), 1561 (νC=C, C6H3-), 1382 (νC-O), 1283,
1241 (νC-C), 1192 (νC-N), 736, 608 (δC-H, C6H3-); 1H NMR (300
MHz, CDCl3) δ (ppm): 0.77 (s, 3H, 10-CH3), 1.33 (d, J = 9.7
Hz, 1H, 6-CH), 1.39 (s, 3H, 11-CH3), 2.35 (m, 1H, 8-CH),
2.61-2.68 (m, 1H, 9α-CH), 2.80 (t, J = 5.6 Hz, 1H, 9β-CH),
2.92 (d, J = 2.8 Hz, 2H, 5-CH2), 3.91 (s, 3H, Ar-OCH3), 5.88
(s, 2H, NH2), 6.83-6.95 (m, 2H, 2', 3'-CH), 7.23 (t, J = 1.3 Hz,
1H, 6'-CH), 11.16 (s, 1H,Ar-OH); 13C NMR (300 MHz, CDCl3)
δ (ppm): 21.18, 25.68, 29.66, 30.17, 38.74, 40.22, 49.71, 56.11,
112.82, 114.46, 118.29, 121.33, 147.52, 148.48, 158.70,
161.91, 175.81, 177.59; MS m/z (% relative intensity): 311
(M+, 88), 310 (29), 296 (66), 268 (100), 252 (24), 238 (8),
196 (6), 167 (3), 119 (13), 77 (10), 65 (4), 51 (3); Anal. Calcd
for C18H21N3O2: C, 69.42; N, 13.50; H, 6.81. Found: C, 69.38;
N, 13.47; H, 6.87.
Synthesis of compound 3g: A mixture of 2g (1.30 g, 5
mmol), guanidine hydrochloride (0.95 g, 10 mmol), NaOH
(1.20 g, 30 mmol), distilled water (1.20 g) and ethanol (30
mL) was refluxed for 9 h, other conditions reference 3a.
colourless transparent crystal; yield = 90.2 %; purity of 99.4 %;
m.p. 111.8-112.1 °C; [α]D20 = -117.6° (c = 0.5, CH3OH). IR
(KBr, νmax, cm-1): 3316, 3191 (νN-H, NH2), 1701 (νC=N), 1624
(δN-H, NH2), 1578, 1560 (νC=C, C6H4-), 1269 (νC-C), 1089 (νC-N),
833, 800 (δC-H, C6H4-); 1H NMR (500 MHz, CDCl3) δ (ppm):
0.76 (s, 3H, 10-CH3), 1.31 (d, J = 9.8 Hz, 1H, 6-CH), 1.40 (s,
3H, 11-CH3), 2.32 (m, 1H, 9α-CH), 2.66 (m, 1H, 9β-CH),
2.75 (t, J = 3.2 Hz, 2H, 5-CH2), 2.81 (t, J = 5.5 Hz, 1H, 8-CH),
6.06 (s, 2H, NH2), 7.42 (m, 2H, 3', 5'-CH), 7.52 (m, 2H, 2', 6'-
CH); 13C NMR (500 MHz, CDCl3) δ (ppm): 21.24, 25.73,
29.18, 29.77, 38.80, 40.19, 49.20, 113.65, 128.56, 129.78,
135.23, 136.06, 160.52, 162.99, 175.95; MS m/z (% relative
intensity): 299 (M+, 41), 284 (25), 270 (9), 256 (37), 243 (11),
231 (11), 221 (6), 147 (7), 138 (5), 119 (100), 91 (5), 77 (13),
51 (4); Anal. Calcd for C17H18N3Cl: C, 68.10; N, 14.02; H,
6.06. Found: C, 68.15; N, 13.93; H, 6.12.
Synthesis of compound 3d: A mixture of 2d (1.28 g, 5
mmol), guanidine hydrochloride (0.95 g, 10 mmol), NaOH
(1.20 g, 30 mmol), distilled water (1.20 g) and ethanol (30
mL) was refluxed for 12 h, other conditions reference 3a.
colourless transparent crystal; yield = 73.4 %; purity of 99 %;
m.p. 175.5-176.1 °C; [α]D20 = -152.8° (c = 0.5, CH3OH). IR
(KBr, νmax, cm-1): 3311, 3186 (νN-H, NH2), 1735 (νC=N), 1609
(δN-H, NH2), 1581, 1560 (νC=C, C6H4-), 1512 (νas C-O-C), 1250
(νs C-O-C), 1196, 1174 (νC-C), 1037 (νC-N), 834, 801 (δC-H, C6H4-);
1H NMR (500 MHz, CDCl3) δ (ppm): 0.75 (s, 3H, 10-CH3),
1.32 (d, J = 9.7 Hz, 1H, 6-CH), 1.38 (s, 3H, 11-CH3), 2.32 (m,
1H, 9α-CH), 2.63 (m, 1H, 9β-CH), 2.75 (t, J = 5.5 Hz, 1H,
8-CH), 2.84 (m, 2H, 5-CH2), 3.84 (s, 3H, Ar-OCH3), 5.19 (s,
2H, NH2), 6.96 (m, 2H, 3', 5'-CH), 7.60 (m, 2H, 2', 6'-CH);
13C NMR (500 MHz, CDCl3) δ (ppm): 21.21, 25.79, 29.58,
29.89, 38.71, 40.41, 50.29, 55.27, 113.60, 113.76, 129.88,
131.00, 160.06, 160.79, 163.16, 176.43; MS m/z (% relative
intensity): 295 (M+, 74), 294 (66), 280 (40), 266 (13), 252
(49), 239 (15), 227 (29), 208 (5), 147 (9), 134 (8), 119 (100),
91 (7), 77 (14), 65 (4), 51 (3); Anal. Calcd for C18H21N3O: C,
73.18; N, 14.23; H, 7.18. Found: C, 73.24; N, 14.14; H, 7.27.
Synthesis of compound 3e: A mixture of 2e (1.36 g, 5
mmol), guanidine hydrochloride (0.95 g, 10 mmol), potassium
tert-butoxide (2.24 g, 20 mmol), methylbenzene (30 mL) and
ethanol (5 mL) was refluxed for 13 h, other conditions refe-
rence 3a. colourless transparent crystal; yield = 62.1 %; purity
20
of 98.8 %; m.p. 222.8-223.5 °C; [α]D = -69.0° (c = 0.1,
Synthesis of compound 3h: A mixture of 2h (1.30 g, 5
mmol), guanidine hydrochloride (0.95 g, 10 mmol), sodium
ethoxide (1.36 g, 20 mmol) and ethanol (30 mL) was refluxed
for 4 h, then KMnO4 (0.79 g, 5 mmol) was added for another
2 h, other conditions reference 3a. colourless transparent
crystal; yield = 75.9 %; purity of 98.7 %; m.p. 107.8-108.6 °C;
[α]D20 = -143.0° (c = 0.1, CH3OH). IR (KBr, νmax, cm-1): 3318,
CH3OH). IR (KBr, νmax, cm-1): 3465 (νO-H), 3440 (fermi reso-
nance f 2 δN-H and νas N-H), 3310, 3184 (νN-H, NH2), 1637 (νC=N),
1608 (δN-H, NH2), 1566, 1514 (νC=C, C6H3-), 1370 (νC-O), 1270
(νC-C), 1232 (νC-N), 806, 778 (δC-H,C6H3-); 1H NMR (300 MHz,
CDCl3) δ (ppm): 0.77 (s, 3H, 10-CH3), 1.33 (d, J = 9.7 Hz,
1H, 6-CH), 1.39 (s, 3H, 11-CH3), 2.34 (t, J = 2.8 Hz, 1H, 8-
CH), 2.61-2.90 (m, 4H, 9, 5-CH2), 3.92 (s, 3H, Ar-OCH3),
5.98 (s, 2H, NH2), 6.92-6.95 (d, J = 8.0 Hz, 1H, 3'-CH), 7.13-
7.26 (m, 2H, 2', 6'-CH), 9.19 (s, 1H, Ar-OH); 13C NMR (300
MHz, CDCl3) δ (ppm): 21.20, 25.72, 29.63, 29.78, 38.74,
40.30, 49.29, 55.96, 111.49, 113.52, 114.08, 122.05, 129.56,
146.59, 160.30, 163.57, 175.79, 176.35; MS m/z (% relative
intensity): 311 (M+, 100), 296 (54), 282 (15), 268 (71), 253
(21), 243 (22), 236 (7), 224 (6), 119 (93), 115 (7), 91 (9), 77
(15), 65 (5), 51 (5); Anal. Calcd for C18H21N3O2: C, 69.42;
N, 13.50; H, 6.81. Found: C, 69.39; N, 13.57; H, 6.83.
3200 (νN-H, NH2), 1708 (νC=N), 1640 (δN-H, NH2), 1577 (νC=C
,
1
C6H4-), 1264 (νC-C), 760 (δC-H, C6H4-); H NMR (300 MHz,
CDCl3) δ (ppm): 0.78 (s, 3H, 10-CH3), 1.33 (d, J = 9.8 Hz,
1H, 6-CH), 1.39 (s, 3H, 11-CH3), 2.25 (s, 1H, 8-CH), 2.48 (s,
2H, 5-CH2), 2.65-2.70 (m, 1H, 9α-CH), 2.80 (t, J = 5.3 Hz,
1H, 9β-CH), 5.97 (s, 2H, NH2), 7.26 (t, J = 5.6 Hz, 1H, 3'-
CH), 7.35 (m, 2H, 4', 5'-CH), 7.46 (t, J = 3.9 Hz, 1H, 6'-CH);
13C NMR (300 MHz, CDCl3) δ (ppm): 21.18, 25.90, 27.92,
30.03, 39.29, 39.97, 49.18, 115.17, 126.96, 129.29, 129.66,
129.90, 136.60, 160.33, 163.11, 175.72, 176.50; MS m/z (%