3.2.1. General Procedure for the Synthesis of the Target Compounds 5a–h

The appropriate

N

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-acetylisatin 4a–d (1 mmol) was added to a suspension containing the proper acid hydrazide 3a,b (1 mmol) in acetonitrile (15 mL). The reaction mixture was heated to reflux for two hours, cooled to room temperature, and filtered. The collected solid was dried and re-crystallized from ethanol to give the title compounds 5a–h.

N

-(2-{[2-(1

H

-Indol-2-ylcarbonyl)hydrazinyl](oxo)acetyl}phenyl)acetamide (5a): Yellow powder; m.p. 249–250 °C (yield 58%); 1H-NMR (DMSO-

d

6): δ (ppm) 2.20 (s, 3H, C

H

3), 7.09 (t,

J

= 7.5 Hz, 1H, Ar-H), 7.24 (t,

J

= 7.5 Hz, 1H, Ar-H), 7.27 (d,

J

= 1.5 Hz, 1H, CH-3-indole), 7.31 (t,

J

= 7.5 Hz, 1H, Ar-H), 7.47 (d,

J

= 8.5 Hz, 1H, Ar-H), 7.68 (d,

J

= 8.0 Hz, 1H, Ar-H), 7.73 (dd,

J

= 1.5, 8.5 Hz, 1H, Ar-H), 8.11 (dd,

J

= 1.0, 8.0 Hz, 1H, Ar-H), 8.21 (d,

J

= 8.0 Hz, 1H, Ar-H), 10.71 (s, 1H, NH), 10.75 (s, 1H, NH), 10.90 (s, 1H, NH), 11.85 (s, 1H, NH-indole); 13C-NMR (DMSO-

d

6): δ (ppm) 24.9 (

C

H3), 104.2, 112.9, 120.5, 121.5, 121.9, 122.3, 123.6, 124.4, 127.4, 129.5, 133.5, 135.9, 137.3, 140.3 (Ar-CH and Ar-C), 158.3, 164.5, 169.6, 192.7 (4× C=O); MS

m

/

z

(ESI): 363 [M − H]−; HR-MS (MALDI) calcd for C19H16N4O4: 363.1093, found: 363.1028 (M − H).

N

-(4-Bromo-2-{[2-(1

H

-indol-2-ylcarbonyl)hydrazinyl](oxo)acetyl}phenyl)acetamide (5b): Yellow powder; m.p. 261–263 °C (yield 56%); 1H-NMR (DMSO-

d

6): δ (ppm) 2.19 (s, 3H, C

H

3), 7.08 (t,

J

= 7.5 Hz, 1H, Ar-H), 7.24 (t,

J

= 7.5 Hz, 1H, Ar-H), 7.27 (d,

J

= 1.5 Hz, 1H, CH-3-indole), 7.49 (d,

J

= 8.5 Hz, 1H, Ar-H), 7.68 (d,

J

= 8.0 Hz, 1H, Ar-H), 7.89 (dd,

J

= 2.0, 8.5 Hz, 1H, Ar-H), 7.96 (d,

J

= 8.5 Hz, 1H, Ar-H), 8.08 (d,

J

= 2.5 Hz, 1H, Ar-H), 10.65 (s, 1H, NH), 10.68 (s, 1H, NH), 10.91 (s, 1H, NH), 11.83 (s, 1H, NH-indole); 13C-NMR (DMSO-

d

6): δ (ppm) 24.7 (

C

H3), 104.3, 112.9, 114.0, 115.4, 120.2, 122.3, 123.7, 124.4, 127.3, 129.5, 133.4, 134.6, 137.5, 138.6 (Ar-CH and Ar-C), 158.3, 160.6, 169.4, 192.6 (4× C=O); MS

m

/

z

(ESI): 441 [M − H]−, 442 [(M + 1) − H]−, 443[(M + 2) − H]−; HR-MS (MALDI) calcd for C19H15BrN4O4: 441.0198, found: 441.0206 (M − H).

N

-(4-Chloro-2-{[2-(1

H

-indol-2-ylcarbonyl)hydrazinyl](oxo)acetyl}phenyl)acetamide (5c): Yellow powder; m.p. 259–260 °C (yield 77%); 1H-NMR (DMSO-

d

6): δ (ppm) 2.19 (s, 3H, C

H

3), 7.08 (t,

J

= 7.5 Hz, 1H, Ar-H), 7.24 (t,

J

= 7.5 Hz, 1H, Ar-H), 7.27 (d,

J

= 1.5 Hz, 1H, CH-3-indole), 7.48 (d,

J

= 8.0 Hz, 1H, Ar-H), 7.68 (d,

J

= 8.0 Hz, 1H, Ar-H), 7.77 (dd,

J

= 2.5, 8.5 Hz, 1H, Ar-H), 7.99 (d,

J

= 2.5 Hz, 1H, Ar-H), 7.02 (d,

J

= 8.5 Hz, 1H, Ar-H), 10.66 (s, 1H, NH), 10.69 (s, 1H, NH), 10.91 (s, 1H, NH), 11.83 (s, 1H, NH-indole); 13C-NMR (DMSO-

d

6): δ (ppm) 24.7 (

C

H3), 104.3, 112.9, 120.5, 122.3, 123.8, 124.4, 124.8, 127.4, 127.7, 129.5, 131.7, 134.9, 137.2, 138.2 (Ar-CH and Ar-C), 160.9, 163.4, 169.7, 190.2 (4 × C=O); MS

m

/

z

(ESI): 397 [M − H]−, 398 [(M + 1) − H]−, 399 [(M + 2) − H]−; HR-MS (MALDI) calcd for C19H15ClN4O4: 397.0704, found: 397.0738 (M − H).

N

-(4-Fluoro-2-{[2-(1

H

-indol-2-ylcarbonyl)hydrazinyl](oxo)acetyl}phenyl)acetamide (5d): Yellow powder; m.p. 268–270 °C(yield 73%); 1H-NMR (DMSO-

d

6): δ (ppm) 2.17 (s, 3H, C

H

3), 7.08 (t,

J

= 7.5 Hz, 1H, Ar-H), 7.24 (t,

J

= 8.0 Hz, 1H, Ar-H), 7.27 (d,

J

= 1.5 Hz, 1H, CH-3-indole), 7.47 (d,

J

= 8.5 Hz, 1H, Ar-H), 7.60 (ddd,

J

= 2.5, 3.0, 8.5 Hz, 1H, Ar-H), 7.68 (d,

J

= 8.0 Hz, 1H, Ar-H), 7.84 (dd,

J

= 3.0, 9.5 Hz, 1H, Ar-H), 7.97–7.99 (m, 1H, Ar-H), 10.55 (s, 1H, NH), 10.69 (s, 1H, NH), 10.89 (s, 1H, NH), 11.85 (s, 1H, NH-indole); 13C-NMR (DMSO-

d

6): δ (ppm) 24.5 (

C

H3), 104.3, 112.9, 118.4, 118.5, 120.5, 122.2, 122.3, 124.4, 127.4, 129.5, 130.4, 133.2, 135.6, 137.7 (Ar-CH and Ar-C), 161.1, 163.6, 169.6, 190.1 (4× C=O); MS

m

/

z

(ESI): 381 [M − H]−; HR-MS (MALDI) calcd for C19H15FN4O4: 381.0999, found: 381.0951 (M − H).

N

-{2-[{2-[(5-Methoxy-1

H

-indol-2yl)carbonyl]hydrazinyl}(oxo)acetyl]phenyl}acetamide (5e): Pale yellow powder; m.p. 228-230 °C (yield 52%); 1H-NMR (DMSO-

d

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6): δ (ppm) 2.19 (s, 3H, C

H

3), 3.78 (s, 3H, OC

H

3), 6.90 (dd,

J

= 2.5, 8.5 Hz, 1H, Ar-H), 7.15 (d,

J

= 1.0 Hz, 1H, Ar-H), 7.19 (s, 1H, CH-3-indole), 7.31(t,

J

= 7.5 Hz, 1H, Ar-H), 7.35 (d,

J

= 9.0 Hz, 1H, Ar-H), 7.72 (t,

J

= 8.0 Hz, 1H, Ar-H), 8.11 (d,

J

= 8.0 Hz, 1H, Ar-H), 8.20 (d,

J

= 8.5 Hz, 1H, Ar-H), 10.66 (s, 1H, NH), 10.75 (s, 1H, NH), 10.89 (s, 1H, NH), 11.71 (s, 1H, NH-indole); 13C-NMR (DMSO-

d

6): δ (ppm) 24.9 (

C

H3), 55.7 (O

C

H3), 102.6, 103.9, 113.7, 115.8, 121.5, 121.9, 123.6, 127.8, 129.8, 132.5, 133.5, 135.9, 140.3, 154.4 (Ar-CH and Ar-C), 160.9, 164.5, 169.6, 192.7 (4× C=O); MS

m

/

z

(ESI): 393 [M − H]−; HR-MS (MALDI) calcd for C20H18N4O5: 393.1199, found: 393.1139 (M − H).

N

-{4-Bromo-2-[{2-[(5-methoxy-1

H

-indol-2-yl)carbonyl]hydrazinyl}(oxo)acetyl]phenyl}acetamide (5f): Light brown powder; 248–250 °C (yield 65%); 1H-NMR (DMSO-

d

6): δ (ppm) 2.18 (s, 3H, C

H

3), 3.78 (s, 3H, OC

H

3), 6.89 (dd,

J

= 2.5, 9.0 Hz, 1H, Ar-H), 7.14 (d,

J

= 2.0 Hz, 1H, Ar-H), 7.19 (d,

J

= 1.5 Hz, 1H, CH-3-indole), 7.36 (d,

J

= 8.5 Hz, 1H, Ar-H), 7.89 (dd,

J

= 2.0, 8.5 Hz, 1H, Ar-H), 7.97 (d,

J

= 9.0 Hz, 1H, Ar-H), 8.08 (d,

J

= 2.5 Hz, 1H, Ar-H), 10.62 (s, 1H, NH), 10.65 (s, 1H, NH), 10.88 (s, 1H, NH), 11.68 (s, 1H, NH-indole); 13C-NMR (DMSO-

d

6): δ (ppm) 24.7 (

C

H3), 55.7 (O

C

H3), 102.5, 103.9, 113.7, 115.4, 115.7, 123.9, 125.0, 127.7, 129.8, 132.5, 134.5, 137.8, 138.6, 154.4 (Ar-CH and Ar-C), 160.9, 163.4, 169.7, 190.1 (4× C=O); MS

m

/

z

(ESI): 471 [M − H]−, 472 [(M + 1) − H]−, 473 [(M + 2) − H]−; HR-MS (MALDI) calcd for C20H17BrN4O5: 471.0304, found: 471.0365 (M − H).

N

-{4-Chloro-2-[{2-[(5-methoxy-1

H

-indol-2-yl)carbonyl]hydrazinyl}(oxo)acetyl]phenyl}acetamide (5g): Yellow powder; 255–257 °C (yield 77%); 1H-NMR (DMSO-

d

6): δ (ppm) 2.18 (s, 3H, C

H

3), 3.78 (s, 3H, OC

H

3), 6.89 (dd,

J

= 2.0, 9.0 Hz, 1H, Ar-H), 7.14 (d,

J

= 2.5 Hz, 1H, Ar-H), 7.19 (d,

J

= 2.0 Hz, 1H, CH-3-indole), 7.36 (d,

J

= 8.5 Hz, 1H, Ar-H), 7.78 (dd,

J

= 2.5, 9.0 Hz, 1H, Ar-H), 7.99 (d,

J

= 2.5 Hz, 1H, Ar-H), 8.03 (d,

J

= 9.0 Hz, 1H, Ar-H), 10.63 (s, 1H, NH), 10.65 (s, 1H, NH), 10.89 (s, 1H, NH), 11.68 (s, 1H, NH-indole); 13C-NMR (DMSO-

d

6): δ (ppm) 24.7 (

C

H3), 55.7 (O

C

H3), 102.5, 103.9, 113.7, 115.7, 123.8, 124.7, 127.6, 127.7, 129.7, 131.7, 132.6, 134.9, 138.3, 154.4 (Ar-CH and Ar-C), 160.9, 163.5, 169.7, 190.2 (4× C=O); MS

m

/

z

(ESI): 427 [M − H]−, 428 [(M + 1) − H]−, 429 [(M + 2) − H]−; HR-MS (MALDI) calcd for C20H17ClN4O5: 427.0809, found: 427.0845 (M − H).

N

-{4-Fluoro-2-[{2-[(5-methoxy-1

H

-indol-2-yl)carbonyl]hydrazinyl}(oxo)acetyl]phenyl}acetamide (5h): Yellow powder; 238–240 °C (yield 60%); 1H-NMR (DMSO-

d

6): δ (ppm) 2.17 (s, 3H, C

H

3), 3.78 (s, 3H, OC

H

3), 6.89 (dd,

J

= 2.5, 9.0 Hz, 1H, Ar-H), 7.14 (d,

J

= 2.0 Hz, 1H, Ar-H), 7.18 (d,

J

= 1.5 Hz, 1H, CH-3-indole), 7.35 (d,

J

= 9.0 Hz, 1H, Ar-H), 7.60 (ddd,

J

= 2.5, 3.0, 9.0 Hz, 1H, Ar-H), 7.85 (dd,

J

= 3.0, 9.0 Hz, 1H, Ar-H), 7.99 (dd,

J

= 1.0, 9.0 Hz, 1H, Ar-H), 10.55 (s, 1H, NH), 10.64 (s, 1H, NH), 10.87 (s, 1H, NH), 11.70 (s, 1H, NH-indole); 13C-NMR (DMSO-

d

6): δ (ppm) 24.5 (

C

H3), 55.8 (O

C

H3), 102.6, 103.9, 113.7, 115.8, 122.2, 122.4, 124.4, 124.5, 127.8, 129.7, 132.6, 135.9, 142.4, 154.4 (Ar-CH and Ar-C), 160.9, 163.7, 169.6, 190.3 (4× C=O); MS

m

/

z

(ESI): 411 [M − H]−; HR-MS (MALDI) calcd for C20H17FN4O5: 411.1105, found: 411.1148 (M − H).

H

-indol-2-ylcarbonyl)amino]acetate (6): White powder; m.p. 222-224 °C [

Ethyl [(1-indol-2-ylcarbonyl)amino]acetate (): White powder; m.p. 222-224 °C [ 35 ].

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