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. Author manuscript; available in PMC: 2014 Apr 5.
Published in final edited form as: Org Lett. 2013 Mar 18;15(7):1540–1543. doi: 10.1021/ol400322v

Table 2.

Domino Synthesis of Fused Acridines 4 and 5

entry product 4 and 5a substrate (1) 2(R1) 3’ time /min yield b/%
1 graphic file with name nihms457709t1.jpg 4a Indoline-2,3-dione (1a) 4-Chlorophenyl (2a) 3a 20 59
2 4b Indoline-2,3-dione (1a) Phenyl (2b) 3a 24 54
3 4c Indoline-2,3-dione (1a) 4-Tolyl (2c) 3a 30 61
4 4d Indoline-2,3-dione (1a) 3,4-Dimethoxyphenyl (2d) 3a 20 50
5 4e 5-Fluoroindoline-2,3-dione (1b) 4-Tolyl (2c) 3a 25 46
6 4f Indoline-2,3-dione (1a) 4-Chlorophenyl (2a) 3b 20 53
7 4g Indoline-2,3-dione (1a) Phenyl (2b) 3b 22 56
8 graphic file with name nihms457709t2.jpg 4h Indoline-2,3-dione (1a) 4-Tolyl (2c) 3b 24 59
9 4i Indoline-2,3-dione (1a) 3,4-Dimethoxyphenyl (2d) 3b 26 51
10 4j Indoline-2,3-dione (1a) 4-Methoxyphenyl (2e) 3b 30 48
11 4k Indoline-2,3-dione (1a) Carboxymethyl (2f) 3b 28 52
12 41 5-Methylindoline-2,3-dione (1c) 4-Chlorophenyl (2a) 3b 26 58
13 4m 5-Methylindoline-2,3-dione (1c) Phenyl (2b) 3b 25 62
14 4n 5-Methylindoline-2,3-dione (1c) 4-Tolyl (2c) 3b 26 64
15 graphic file with name nihms457709t3.jpg 4o 5-Methylindoline-2,3-dione (1c) 4-Methoxyphenyl (2e) 3b 30 49
16 4p 5-Methylindoline-2,3-dione (1c) 4-Bromophenyl (2g) 3b 30 52
17 4q 5-Chloroindoline-2,3-dione (1d) 4-Chlorophenyl (2a) 3b 28 45
18 5a Indoline-2,3-dione (1a) Phenyl (2b) 3c 30 48
19 5b Indoline-2,3-dione (1a) 4-Tolyl (2c) 3c 20 51
20 5c Indoline-2,3-dione (1a) 4-Methoxyphenyl (2e) 3c 30 46
21 5d Indoline-2,3-dione (1a) 3,5-Dichlorophenyl (2g) 3c 30 43
22 graphic file with name nihms457709t4.jpg 5e Indoline-2,3-dione (1a) 4-Chlorophenyl (2a) 3c 28 40
23 5f Indoline-2,3-dione (1a) Phenyl (2b) 3d 25 50
24 5g Indoline-2,3-dione (1a) 4-Tolyl (2c) 3d 28 52
25 5h Indoline-2,3-dione (1a) 3,4-Dimethoxyphenyl (2d) 3d 28 45
26 5i Indoline-2,3-dione (1a) 4-Methoxyphenyl (2e) 3d 30 42
27 5j Indoline-2,3-dione (1a) Carboxymethyl (2f) 3d 30 46
28 5k Indoline-2,3-dione (1a) 3-Chlorophenyl (2h) 3d 28 52
29 51 5-Methylindoline-2,3-dione (1c) 4-Tolyl (2c) 3d 28 55
30 5m 5-Methylindoline-2,3-dione (1c) 4-Methoxyphenyl (2e) 3d 30 50
a

Conditions: the synthesis of products 4, (CH3)2CHCOOH (1.5 mL), 90–100 °C, microwave heating; the synthesis of products 5, (CH3)2CHCOOH (1.5 mL), 130–140 °C, microwave heating.

b

Isolated yield.