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S. Ranganathan et al.
LETTER
Compound 2: mp 143–146 °C (colorless crystals). IR (KBr):
2867, 2819, 1599, 1491, 1240, 1110, 767 cm–1. 1H NMR
(300 MHz, CDCl3): d = 3.40–3.43 (m, 4 H), 3.91–3.95 (m, 4
H), 6.83–6.93 (m, 2 H), 7.21–7.26 (m, 1 H), 8.20 (d, 1 H,
J = 7.7 Hz). 13C NMR (50 MHz, CDCl3): d = 48.0, 66.6,
114.5, 118.2, 127.4, 140.6, 154.1. MS (EI): m/z = 180 [M+].
HRMS: m/z calcd for C9H12N2O2: 180.0899; found:
180.0877.
MHz, D2O): d = 3.73 (s, 4 H), 6.73 (app t, 2 H, J = 7.2 Hz),
6.97 (d, 2 H, J = 7.2 Hz), 7.45 (app t, 2 H, J = 8.4 Hz), 8.02
(d, 2 H, J = 6.6 Hz). 13C NMR (75.47 MHz, D2O): d = 41.2,
107.9, 112.3, 133.2, 137.3, 150.0. MS (EI): m/z = 246 [M+].
HRMS: m/z calcd for C12H14N4O2: 246.1116; found:
246.1105.
Compound 9: pale brown liquid. IR (neat): 3420, 1365 cm–1.
1H NMR (200 MHz, CDCl3): d = 2.79–2.84 (m, 3 H), 3.07
(s, 3 H), 3.33–3.40 (m, 2 H), 3.61–3.67 (m, 2 H), 6.96–7.05
(m, 2 H), 7.42 (app t, 1 H, J = 8.7 Hz), 8.11 (d, 1 H, J = 7.6
Hz). 13C NMR (75.47 MHz, CDCl3): d = 34.4, 37.9, 46.3,
47.9, 115.7, 117.9, 130.3, 139.7, 153.5. MS (EI): m/z = 181
[M+]. HRMS: m/z calcd for C9H15N3O: 181.1215; found:
181.1215.
Compound 10: mp 192–194 °C (pale brown rods). IR (KBr):
3369, 3257, 1615, 1516, 1186, 777 cm–1. 1H NMR (300
MHz, CDCl3): d = 3.04 (s, 6 H), 3.89 (s, 4 H), 6.76 (app t, 2
H, J = 6.8 Hz), 6.82 (d, 2 H, J = 8.5 Hz), 7.16 (app t, 2 H,
J = 8.7 Hz), 8.09 (d, 2 H, J = 7.7 Hz). 13C NMR (50 MHz,
CDCl3): d = 39.2, 49.9, 114.6, 116.3, 127.4, 140.3, 154.4.
MS (EI): m/z = 274 [M+]. HRMS: m/z calcd for C14H18N4O2:
274.1429; found: 274.1419.
Compound 3: thick brown liquid. IR (Neat): 3348, 2932,
1627, 1195 cm–1. 1H NMR (300 MHz, CDCl3): d = 3.38–
3.43 (m, 2 H), 3.90–3.93 (m, 2 H), 6.55–6.63 (m, 2 H), 7.21–
7.27 (m, 1 H), 7.57 (br, 1 H), 8.05 (d, 1 H, J = 7.7 Hz). 13
C
NMR (50 MHz, CDCl3): d = 45.5, 60.5, 106.7, 111.3, 130.2,
137.3, 150.6. MS (EI): m/z = 154 [M+]. HRMS: m/z calcd for
C7H10N2O2: 154.0742; found: 154.0744.
Compound 4: pale brown liquid. IR (neat): 3365, 1506, 1202
cm–1. 1H NMR (200 MHz, CDCl3): d = 3.60–3.65 (m, 4 H),
3.71–3.75 (m, 4 H), 6.88 (app t, 1 H, J = 7.0 Hz), 7.10 (d, 1
H, J = 10.1 Hz), 7.31 (app t, 1 H, J = 8.5 Hz), 8.14 (d, 1 H,
J = 7.9 Hz). 13C NMR (75.47 MHz, CDCl3): d = 52.0, 58.5,
116.7, 117.5, 129.5, 139.7, 152.8. MS (EI): m/z = 198 [M+].
HRMS: m/z calcd for C9H14N2O3: 198.1004; found:
198.1104.
Compound 5: quasi-crystalline brown thick liquid. IR (neat):
2926, 2855, 1241 cm–1. 1H NMR (300 MHz, CDCl3,):
d = 0.84–0.88 (m, 6 H), 1.24 (br, 20 H), 1.52 (br, 4 H), 3.38–
3.43 (m, 4 H), 6.74–6.84 (m, 2 H), 7.14 (app t, 1 H, J = 8.7
Hz), 8.14 (d, 1 H, J = 7.8 Hz). 13C NMR (75.47 MHz,
CDCl3): d = 14.0, 22.4, 26.8, 27.5, 29.0, 29.2, 31.7, 50.5,
116.2, 116.3, 127.8, 140.9, 153.6. MS (EI): m/z = 334 [M+].
HRMS: m/z calcd for C21H38N2O: 334.2984; found:
334.2969.
Compound 6: pale yellow liquid. IR (neat): 2931, 2854,
1622, 1571, 1525, 1196, 750 cm–1. 1H NMR (300 MHz,
CDCl3): d = 1.21–1.45 (m, 6 H), 1.76–1.83 (m, 2 H), 2.00–
2.04 (m, 2 H), 3.27–3.38 (m, 1 H), 6.47–6.60 (m, 2 H), 6.80
(br, 1 H), 7.20 (app t, 1 H, J = 8.3 Hz), 8.11 (d, 1 H, J = 7.4
Hz). 13C NMR (50 MHz, CDCl3): d = 24.6, 25.2, 32.6, 50.5,
105.9, 110.5, 128.2, 137.2, 149.3. MS (EI): m/z = 193 [M+ +
1]. HRMS: m/z calcd for C11H16N2O: 192.1263; found:
192.1164.
Compound 7: mp 180–182 °C (dark brown plates). IR
(KBr): 3423, 3234, 1628, 1575, 1198 cm–1. 1H NMR (200
MHz, D2O): d = 3.23–3.29 (m, 2 H), 3.68–3.74 (m, 2 H),
6.81 (app t, 1 H, J = 6.8 Hz), 6.95 (d, 1 H, J = 8.6 Hz), 7.55
(app t, 1 H, J = 7.8 Hz), 8.02 (d, 1 H, J = 6.6 Hz). 13C NMR
(75.47 MHz, D2O): d = 38.3, 39.0, 108.1, 113.3, 133.7,
137.6, 149.7. MS (EI): m/z = 153 [M+]. HRMS: m/z calcd for
C7H11N3O: 153.0902; found: 153.0899.
Compound 11: pale brown liquid. IR (neat): 2947, 1637 cm–1.
1H NMR (200 MHz, CDCl3): d = 1.70–1.73 (m, 6 H), 3.47–
3.50 (m, 4 H), 6.82 (d, 2 H, J = 7.8 Hz), 8.09 (d, 2 H, J = 8.0
Hz). 13C NMR (75.47 MHz, CDCl3): d = 23.9, 25.0, 47.7,
108.9, 139.3, 150.7. MS (ESI): m/z = 179 [M+ + 1]. HRMS:
m/z calcd for C10H14N2O: 178.1106; found: 178.1091.
Compound 12: thick brown liquid. IR (neat): 3278, 1642,
1539, 1061 cm–1. 1H NMR (300 MHz, D2O): d = 3.36–3.40
(m, 2 H), 3.75–3.81 (m, 2 H), 6.74 (d, 2 H, J = 7.4 Hz), 7.87
(d, 2 H, J = 7.4 Hz). 13C NMR (75.47 MHz, D2O): d = 44.7,
59.6, 108.4, 139.0, 152.5. MS (EI): m/z = 155 [M+ + 1].
HRMS: m/z calcd for C7H10N2O2: 154.0742; found:
154.0644.
Compound 13: quasi-crystalline thick brown liquid. IR
(neat): 2927, 2855, 1466 cm–1. 1H NMR (200 MHz, CDCl3):
d = 0.87–0.92 (m, 6 H), 1.29 (br, 20 H), 1.52 (br, 4 H), 2.57–
2.64 (m, 4 H), 7.27 (d, 2 H, J = 7.9 Hz), 8.15 (d, 2 H, J = 7.9
Hz). 13C NMR (50 MHz, CDCl3): d = 14.2, 22.5, 25.9, 26.8,
29.0, 29.1, 31.6, 47.7, 126.7, 140.3, 157.6. MS (ESI): m/z =
335 [M+ + 1]. HRMS: m/z calcd for C21H38N2O: 334.2984;
found: 334.2964.
Compound 14: pale brown liquid. IR (neat): 3401, 3047,
1643, 1551, 1339, 1218, 815 cm–1. 1H NMR (200 MHz,
D2O): d = 2.78 (br, 3 H), 3.24 (s, 3 H), 3.33–3.49 (m, 2 H),
3.91–4.01 (m, 2 H), 7.03 (d, 2 H, J = 7.3 Hz), 8.15 (d, 2 H,
J = 7.3 Hz). 13C NMR (50 MHz, D2O): d = 35.8, 40.8, 47.8,
50.3, 109.9, 141.6, 160.2. MS (ESI): m/z = 182 [M+ + 1].
HRMS: m/z calcd for C9H15N3O: 181.1215; found:
181.1225.
Compound 8: mp 242–244 °C (pale brown rods). IR (KBr):
3337, 1626, 1578, 1528, 1188, 767 cm–1. 1H NMR (300
Synlett 2007, No. 8, 1215–1218 © Thieme Stuttgart · New York