Comptes Rendus Chimie

CV3 - Editorial Board - English

Fengfeng Che

Yongsheng Wang

Tianhua Shen

Xiaoxia An

Qingbao Song

Supporting information for
Synthesis of 2-(3-amino-2-oxoindolin-3-yl)-3-hydroxynaphthalene-1,4-dione derivatives via a one-pot, three-component reaction under catalyst-free conditions

Fengfeng Chea, Yongsheng Wanga, Tianhua Shena, Xiaoxia Ana and Qingbao Songa,*
a College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. China
* Corresponding author. Tel.: +86 0571 88320284; Fax: +86 0571 88320813.
E-mail address: qbsong@zjut.edu.cn.

Table of contents
1. General remarks
2. Spectroscopic data of compounds 4a-4m
3. 1H NMR and 13C NMR spectrum of compound 4a-4m
4. HRMS (ESI) spectrum of compound 4a-4m

1. General remarks:
Reagents and solvents were commercially available and used without further purification. Melting points were recorded on a Büchi B-545 apparatus in open capillary tubes. Mass spectroscopy was recorded with a Thermo LCQ Fleet MS spectrometer. FTIR spectra were recorded as KBr pellets on a Shimadzu FT IR-8400S spectrometer. X-ray crystallographic intensity data were collected using a Xcalibur, Eos, Gemini Ultra CCD diffractometer equipped with a graphite monochromated Enhance (Mo) X-ray source(λ= 0.71073). 1H NMR (500 MHz) and 13C NMR (126 MHz) spectra were recorded on a Bruker AVANCE III 500-MHz instrument (Bruker, Switzerland) using TMS as internal standard and DMSO as solvents. All reactions were monitored by TLC with Qingdao GF254 silica gel coated plates using UV (254 nm) light to visualize the course of reaction.


2. Spectroscopic data of compounds 4a-4m:
2-(3-amino-2-oxoindolin-3-yl)-3-hydroxynaphthalene-1,4-dione (4a):
Orange solid, m.p. 266-268 oC. IR (KBr, cm-1): 3633, 3573, 3470, 3064, 3012, 1716, 1686, 1662; 1H NMR (500 MHz, DMSO-d6) δ = 10.64 (s, 1H), 9.30 (s, 3H), 7.83 (d, J = 7.5 Hz, 2H), 7.71 (t, J = 7.1 Hz, 1H), 7.59 (td, J = 7.5, 1.2 Hz, 1H), 7.42 (d, J = 7.4 Hz, 1H), 7.25 (td, J = 7.7, 1.1 Hz, 1H), 6.91 (t, J = 7.6 Hz, 1H), 6.87 (d, J = 7.8 Hz, 1H). 13C NMR (126 MHz, DMSO-d6) δ = 184.0, 174.6, 142.7, 133.9, 131.0, 130.9, 129.8, 129.1, 125.4, 125.1, 124.6, 121.7, 109.6, 61.3. HRMS (ESI) Calcd. for C18H11ClN2O4 ([M+H]+): 321.0875. Found: 321.0864. 

2-(3-amino-4-bromo-2-oxoindolin-3-yl)-3-hydroxynaphthalene-1,4-dione (4b):
Yellow solid, m.p. 225-226 oC. IR (KBr, cm-1): 3629, 3546, 3467, 3053, 3041, 1776, 1761, 1678, 525; 1H NMR (500 MHz, DMSO-d6) δ = 10.95 (s, 1H), 9.90 (s, 3H), 7.85 (d, J = 7.4 Hz, 1H), 7.78 – 7.65 (m, 2H), 7.61 (t, J = 6.6 Hz, 1H), 7.22 (t, J = 7.9 Hz, 1H), 7.15 – 7.04 (m, 1H), 6.92 (d, J = 7.6 Hz, 1H). 13C NMR (126 MHz, DMSO-d6) δ = 183.6, 178.4, 174.8, 171.8, 145.2, 134.0, 133.3, 131.4, 130.9, 128.2, 125.5, 125.2, 118.5, 109.2, 108.2, 63.4. HRMS (ESI) Calcd. for C18H11ClN2O4 ([M+H]+): 398.9980. Found: 398.9981.

2-(3-amino-4,7-dichloro-2-oxoindolin-3-yl)-3-hydroxynaphthalene-1,4-dione (4c):
Orange-red solid, m.p. 233-235 oC. IR (KBr, cm-1): 3631, 3532, 3467, 3058, 3038, 1783, 1747, 1676, 669, 658; 1H NMR (500 MHz, DMSO-d6) δ = 11.40 (s, 1H), 9.87 (s, 3H), 7.96 – 7.52 (m, 4H), 7.41 (d, J = 8.7 Hz, 1H), 7.00 (d, J = 8.7 Hz, 1H). 13C NMR (126 MHz, DMSO-d6) δ = 183.6, 178.4, 174.7, 171.8, 142.5, 134.1, 133.2, 131.6, 131.0, 130.9, 128.6, 127.4, 125.6, 125.3, 123.1, 113.0, 107.9, 63.0. HRMS (ESI) Calcd. for C18H11ClN2O4 ([M+H]+): 389.0096. Found: 389.0084.

2-(3-amino-5-fluoro-2-oxoindolin-3-yl)-3-hydroxynaphthalene-1,4-dione (4d):
Yellow solid, m.p. 260-262 oC. IR (KBr, cm-1): 3608, 3545, 3448, 3093, 3062, 1718, 1685, 1674, 1437; 1H NMR (500 MHz, DMSO-d6) δ = 10.65 (s, 1H), 9.27 (s, 3H), 7.83 (d, J = 7.5 Hz, 2H), 7.71 (t, J = 7.5 Hz, 1H), 7.60 (t, J = 7.5 Hz, 1H), 7.22 (dd, J = 8.1, 2.6 Hz, 1H), 7.10 (td, J = 9.1, 2.6 Hz, 1H), 6.86 (dd, J = 8.5, 4.3 Hz, 1H). 13C NMR (126 MHz, DMSO-d6) δ = 184.0, 174.6, 157.7 (d, J = 237.0 Hz), 139.0, 133.9, 131.1, 130.9, 130.3, 125.4, 125.1, 116.0 (d, J = 23.0 Hz), 112.1 (d, J = 25.0 Hz), 110.4 (d, J = 7.8 Hz), 61.4. HRMS (ESI) Calcd. for C18H11ClN2O4 ([M+H]+): 339.0781. Found: 339.0789.    

2-(3-amino-5-chloro-2-oxoindolin-3-yl)-3-hydroxynaphthalene-1,4-dione (4e):
Orange solid, m.p. 240-242 oC. IR (KBr, cm-1): 3604, 3569, 3450, 3087, 3016, 1706, 1674, 1616, 613; 1H NMR (500 MHz, DMSO-d6) δ 10.78 (s, 1H), 9.24 (s, 3H), 7.83 (d, J = 7.2 Hz, 2H), 7.71 (t, J = 6.7 Hz, 1H), 7.60 (t, J = 7.2 Hz, 1H), 7.43 (s, 1H), 7.31 (d, J = 7.8 Hz, 1H), 6.89 (d, J = 8.2 Hz, 1H). 13C NMR (126 MHz, DMSO-d6) δ 183.9, 174.3, 141.6, 133.9, 131.0, 130.9, 130.8, 129.5, 125.4, 125.2, 125.1, 124.5, 111.5, 111.0, 99.5, 60.9. HRMS (ESI) Calcd. for C18H11ClN2O4 ([M+H]+): 355.0486. Found: 355.0488.

2-(3-amino-5-bromo-2-oxoindolin-3-yl)-3-hydroxynaphthalene-1,4-dione (4f):
Orange-red solid, m.p. 228-230 oC. IR (KBr, cm-1): 3629, 3571, 3458, 3068, 3020, 1695, 1651, 1631, 588; 1H NMR (500 MHz, DMSO-d6) δ = 10.77 (s, 1H), 9.23 (s, 3H), 7.83 (d, J = 7.4 Hz, 2H), 7.70 (t, J = 7.3 Hz, 1H), 7.63 – 7.51 (m, 2H), 7.42 (dd, J = 8.3, 1.8 Hz, 1H), 6.84 (d, J = 8.3 Hz, 1H). 13C NMR (126 MHz, DMSO-d6) δ = 184.0, 174.2, 142.0, 133.9, 132.3, 131.3, 131.1, 130.9, 127.2, 125.5, 125.1, 112.8, 111.6, 61.0. ESI-MS (m/z): 399.0 [M+H]+. HRMS (ESI) Calcd. for C18H11ClN2O4 ([M+H]+): 398.9980. Found: 398.9994.

2-(3-amino-5-iodo-2-oxoindolin-3-yl)-3-hydroxynaphthalene-1,4-dione (4g): 
Orange solid, m.p. 197-199 oC. IR (KBr, cm-1): 3606, 3575, 3461, 3030, 3004, 1714, 1672, 1571, 499; 1H NMR (500 MHz, DMSO-d6) δ = 10.75 (s, 1H), 9.22 (s, 3H), 7.85 (d, J = 7.4 Hz, 2H), 7.75 – 7.66 (m, 2H), 7.60 (t, J = 8.4 Hz, 2H), 6.73 (d, J = 8.2 Hz, 1H). 13C NMR (126 MHz, DMSO-d6) δ = 184.0, 174.0, 142.5, 138.1, 133.9, 132.7, 131.6, 131.0, 130.9, 125.4, 125.2, 112.1, 83.8, 60.9. HRMS (ESI) Calcd. for C18H11ClN2O4 ([M+H]+): 446.9842. Found: 446.9820.

2-(3-amino-5-methyl-2-oxoindolin-3-yl)-3-hydroxynaphthalene-1,4-dione (4h):
Orange solid, m.p. 227-229 oC. IR (KBr, cm-1): 3602, 3585, 3469, 3045, 3004, 2630, 1712, 1699, 1639, 1539; 1H NMR (500 MHz, DMSO-d6) δ = 10.54 (s, 1H), 9.28 (s, 3H), 7.96 – 7.66 (m, 3H), 7.59 (td, J = 7.5, 1.2 Hz, 1H), 7.24 (s, 1H), 7.05 (dd, J = 7.9, 0.9 Hz, 1H), 6.77 (d, J = 7.9 Hz, 1H), 2.19 (s, 3H). 13C NMR (126 MHz, DMSO-d6) δ = 184.1, 174.7, 140.2, 133.9, 131.1, 130.9, 130.6, 130.0, 129.2, 125.4, 125.1, 125.0, 124.0, 109.4, 61.4, 20.5. HRMS (ESI) Calcd. for C18H11ClN2O4 ([M+H]+): 335.1032. Found: 335.1036.

2-(3-amino-5-methoxy-2-oxoindolin-3-yl)-3-hydroxynaphthalene-1,4-dione (4i):
Yellow solid, m.p. 229-231 oC. IR (KBr, cm-1): 3600, 3537, 3479, 3050, 3024, 2630, 1710, 1691, 1571, 1239; 1H NMR (500 MHz, DMSO-d6) δ = 10.47 (s, 1H), 9.25 (s, 3H), 7.83 (d, J = 6.4 Hz, 2H), 7.71 (s, 1H), 7.64 – 7.54 (m, 1H), 7.04 (s, 1H), 6.83 (s, 1H), 6.80 (s, 1H), 3.64 (s, 3H). 13C NMR (126 MHz, DMSO-d6) δ = 184.4, 175.0, 155.1, 154.8, 136.2, 134.3, 131.5, 131.1, 130.4, 125.7, 125.5, 125.1, 114.9, 112.6, 111.5, 110.5, 110.2, 61.9, 55.8. HRMS (ESI) Calcd. for C18H11ClN2O4 ([M+H]+): 351.0981. Found: 351.0985.

2-(3-amino-5,7-dimethyl-2-oxoindolin-3-yl)-3-hydroxynaphthalene-1,4-dione (4j):
Orange-red solid, m.p. 230-232 oC. IR (KBr, cm-1): 3612, 3527, 3450, 3057, 3033, 2898, 2757,1698, 1630, 1621, 1470, 1454; 1H NMR (500 MHz, DMSO-d6) δ = 10.60 (s, 1H), 9.31 (s, 3H), 7.82 (d, J = 7.2 Hz, 2H), 7.70 (s, 1H), 7.59 (t, J = 7.4 Hz, 1H), 7.06 (s, 1H), 6.88 (s, 1H), 2.21 (s, 3H), 2.15 (s, 3H). 13C NMR (126 MHz, DMSO-d6) δ = 184.9, 175.1, 160.1, 147.1, 138.8, 133.9, 131.8, 131.4, 131.9, 130.9, 130.5, 125.4, 125.2, 122.3, 121.4, 118.6, 117.57, 61.7, 20.5, 16.4. HRMS (ESI) Calcd. for C18H11ClN2O4 ([M+H]+): 349.1188. Found: 349.1178.

2-(3-amino-6-chloro-2-oxoindolin-3-yl)-3-hydroxynaphthalene-1,4-dione (4k):
Orange solid, m.p. 251-253 oC. IR (KBr, cm-1): 3593, 3540, 3477, 3100, 3018, 1731, 1681, 1645, 572; 1H NMR (500 MHz, DMSO-d6) δ = 10.80 (s, 1H), 9.28 (s, 3H), 7.83 (d, J = 7.4 Hz, 2H), 7.71 (t, J = 7.3 Hz, 1H), 7.60 (t, J = 7.4 Hz, 1H), 7.40 (d, J = 8.0 Hz, 1H), 6.97 (dd, J = 8.0, 1.7 Hz, 1H), 6.88 (d, J = 1.5 Hz, 1H). 13C NMR (126 MHz, DMSO-d6) δ = 184.0, 174.6, 144.2, 134.0, 134.0, 131.1, 130.9, 127.9, 126.1, 125.4, 125.2, 121.4, 109.6, 60.8. HRMS (ESI) Calcd. for C18H11ClN2O4 ([M+H]+): 355.0486. Found: 355.0475.

2-(3-amino-2-oxo-7-(trifluoromethyl)indolin-3-yl)-3-hydroxynaphthalene-1,4-dione (4l): 
Orange solid, m.p. 195-197 oC. IR (KBr, cm-1): 3647, 3558, 3483, 3041, 3032, 1695, 1684, 1633, 1454; 1H NMR (500 MHz, DMSO-d6) δ = 11.12 (s, 1H), 9.34 (s, 3H), 7.83 (d, J = 7.4 Hz, 2H), 7.71 (d, J = 7.3 Hz, 1H), 7.68 (d, J = 7.4 Hz, 1H), 7.59 (td, J = 7.5, 1.1 Hz, 1H), 7.53 (d, J = 8.0 Hz, 1H), 7.10 (t, J = 7.7 Hz, 1H). 13C NMR (126 MHz, DMSO-d6) δ = 184.0, 175.1, 140.1, 134.0, 131.2, 131.0, 130. 9, 128.6, 126.2, 125.5, 125.2, 123.6 (q, J = 271.8 Hz), 121.8, 110.5 (q, J = 32.8 Hz), 60.0, 21.0. HRMS (ESI) Calcd. for C18H11ClN2O4 ([M+H]+): 389.0749. Found: 389.0738.
, 
2-(3-amino-1-benzyl-2-oxoindolin-3-yl)-3-hydroxynaphthalene-1,4-dione (4m):
Orange-red solid, m.p. 187-189 oC. IR (KBr, cm-1): 3593, 3560, 3521, 3086, 3066, 3026, 2925, 1714, 1695, 1682; 1H NMR (500 MHz, DMSO-d6) δ = 9.44 (s, 3H), 7.85 (d, J = 7.0 Hz, 2H), 7.77 – 7.64 (m, 3H), 7.61 (t, J = 7.2 Hz, 1H), 7.53 (d, J = 7.2 Hz, 1H), 7.39 (t, J = 7.1 Hz, 2H), 7.31 (t, J = 6.8 Hz, 1H), 7.23 (t, J = 7.4 Hz, 1H), 6.98 (t, J = 7.3 Hz, 1H), 6.74 (d, J = 5.5 Hz, 1H), 5.05 (d, J = 15.9 Hz, 1H), 4.93 (d, J = 11.3 Hz, 1H). 13C NMR (126 MHz, DMSO-d6) δ = 184.1, 173.5, 143.3, 136.3, 134.0, 131.2, 130.9, 129.8, 128.5, 127.6, 127.3, 125.5, 125.3, 124.5, 122.5, 109.2, 94.8, 60.9, 43.8. HRMS (ESI) Calcd. for C18H11ClN2O4 ([M+H]+): 411.1345. Found: 411.1339.

3. 1H NMR and 13C NMR Spectrum of Compound 4a-4m


1H NMR Spectrum of Compound 4a



13C NMR Spectrum of Compound 4a

1H NMR Spectrum of Compound 4b





13C NMR Spectrum of Compound 4b

1H NMR Spectrum of Compound 4c





13C NMR Spectrum of Compound 4c

1H NMR Spectrum of Compound 4d





13C NMR Spectrum of Compound 4d

1H NMR Spectrum of Compound 4e





13C NMR Spectrum of Compound 4e

1H NMR Spectrum of Compound 4f





13C NMR Spectrum of Compound 4f

1H NMR Spectrum of Compound 4g





13C NMR Spectrum of Compound 4g

1H NMR Spectrum of Compound 4h





13C NMR Spectrum of Compound 4h

1H NMR Spectrum of Compound 4i


                                   
                                   

13C NMR Spectrum of Compound 4i

1H NMR Spectrum of Compound 4j





13C NMR Spectrum of Compound 4j

1H NMR Spectrum of Compound 4k





13C NMR Spectrum of Compound 4k

1H NMR Spectrum of Compound 4l





13C NMR Spectrum of Compound 4l

1H NMR Spectrum of Compound 4m





13C NMR Spectrum of Compound 4m
4. HRMS (ESI) spectrum of compound 4a-4m






































































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CV3 - Editorial Board - English

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