ACCEPTED MANUSCRIPT
(100 MHz, DMSO-d
6
) δ 178.3, 139.8, 136.0, 133.0, 131.8, 130.4, 129.1, 126.5, 125.1, 121.0,
1
4
2
18.2, 117.6, 111.1, 110.1, 109.5, 61.2, 39.1, 21.7, 20.5.
.2.11. 5,7-Dimethyl-2',3',4',9'-tetrahydrospiro[indoline-3,1'-pyrido[3,4-b]indol]-2-one (3i)
-(1H-indol-3-yl)ethan-1-amine 1a (50 mg, 0.31 mmol) and 5,7-dimethylisatin 2i (55 mg, 0.31
mmol) were reacted using the general procedure A. The product was obtained as a white solid
1
(50 mg, 51%); mp 266-268 °C; R
f
0.25 (CHCl
3
/MeOH = 99/1); H NMR (400 MHz, DMSO-d
6
)
δ 10.38 (br s, 1H), 10.36 (br s, 1H), 7.44 (d, J = 7.6 Hz, 1H), 7.20-7.13 (m, 1H), 7.07-6.92 (m,
2
H), 6.90-6.87 (m, 1H), 6.76-6.68 (m, 1H), 3.59 (ddd, J = 12.7, 7.9, 4.8 Hz, 1H), 3.13 (dt, J =
2.6, 4.8 Hz, 1H), 2.87-2.66 (m, 2H), 2.25 (s, 3H), 2.15 (s, 3H) (one -NH proton was not seen);
1
1
3
C NMR (100 MHz, DMSO-d ) δ 178.7, 138.3, 136.0, 132.6, 132.0, 130.5, 130.4, 126.5, 122.4,
6
1
4
2
20.9, 118.7, 118.2, 117.6, 111.0, 110.0, 61.4, 39.1, 21.7, 20.4, 16.4.
.2.12. 5-Methoxy-2',3',4',9'-tetrahydrospiro[indoline-3,1'-pyrido[3,4-b]indol]-2-one (3j)
-(1H-indol-3-yl)ethan-1-amine 1a (50 mg, 0.31 mmol) and 5-methoxyisatin 2j (56 mg, 0.31
mmol) were reacted using the general procedure A. The product was obtained as a Orange solid
1
(
45 mg, 45%); mp 253-255 °C; R 0.25 (CHCl /MeOH = 99/1); H NMR (400 MHz, DMSO-d )
f
3
6
δ 10.40 (br s, 1H), 10.27 (br s, 1H), 7.45 (d, J = 7.6 Hz, 1H), 7.17 (d, J = 7.8 Hz, 1H), 7.06-6.93
m, 2H), 6.85-6.81 (m, 2H), 6.69 (d, J = 1.6 Hz, 1H), 3.65-3.57 (m, 4H), 3.12 (dt, J= 12.5, 4.6
Hz, 1H), 2.88 (ddd, J = 13.5, 8.2, 5.2 Hz, 1H), 2.72 (dt, J = 15.1, 4.4 Hz, 1H) (one -NH proton
(
1
3
was not seen); C NMR (100 MHz, DMSO-d
6
) δ 178.3, 154.9, 136.1, 135.5, 133.9, 131.7,
1
4
2
26.6, 121.1, 118.3, 117.7, 114.0, 111.1, 110.2, 61.5, 55.4, 40.1, 21.6.
.2.13. 2',3',4',5'-Tetrahydrospiro[indoline-3,1'-pyrido[4,3-b]indol]-2-one (3k)
-(1H-indol-2-yl)ethan-1-amine 1b (50 mg, 0.31 mmol) and isatin 2a (46 mg, 0.31 mmol) were
reacted using the general procedure A. The product was obtained as a brown solid (61 mg, 68%);
1
mp 184-186 °C; R
f
0.25 (CHCl
3
/MeOH = 99/1); H NMR (500 MHz, DMSO-d
6
) δ 10.97 (br s,
1
6
1
H), 10.39 (br s, 1H), 7.25-7.20 (m, 2H), 7.00 (d, J = 7.2 Hz, 1H), 6.94 (d, J = 7.7 Hz, 1H), 6.91-
.83 (m, 2H), 6.66 (t, J = 7.4 Hz, 1H), 6.36 (d, J = 7.8 Hz, 1H), 3.72-3.67 (m, 1H), 3.16-3.11 (m,
1
3
H), 2.92-2.89 (m, 1H), 2.77-2.72 (m, 1H) (one -NH proton was not seen); C NMR (125 MHz,
DMSO-d ) δ 179.6, 141.9, 135.7, 135.3, 131.5, 128.6, 124.6, 124.3, 121.6, 120.2, 118.4, 116.8,
6
-1
+
1
10.8, 109.3, 60.7, 38.5, 23.3; FTIR ν 3033, 2922, 1627, 1032, 788, cm ; HRMS (ESI) [M + H]
found m/z 290.1289, calcd for C H N O 290.1288.
1
8
16
3
1
2