Synthesis and bio-evaluation of quaternary centered 3-hydroxy-3-(trifluoromethyl)indolin-2-…
5-Bromo-3-hydroxy-1-propyl-3-(trifluoromethyl)indolin-2-
1-Benzyl-3-hydroxy-5-iodo-3-(trifluoromethyl)indolin-2-
one (16, C16H11F3INO2)
one (12, C12H11BrF3NO2)
1
1
Isolated yield: 72 %; white solid; m.p.: 128–130 °C; H
Isolated yield: 80 %; white solid; m.p.: 148–150 °C; H
NMR (500 MHz, CDCl3 ? DMSO-d6): d = 7.82 (s, 1H),
7.63–7.62 (d, 1H, J = 8.3 Hz), 7.37–7.28 (m, 4H),
7.23–7.21 (d, 2H, J = 8.0 Hz), 6.52–6.50 (d, 1H,
J = 8.3 Hz), 5.07–5.03 (d, 1H, J = 15.7 Hz), 4.75–4.71
(d, 1H, J = 15.7 Hz), 4.23 (s, 1H) ppm; 13C NMR
(100 MHz, DMSO-d6): d = 42.9, 84.7, 111.1, 120.5,
124.3, 125.8, 125.9, 126.2, 127.0, 127.3, 128.0, 133.6,
139.0, 142.3, 169.7 ppm; 19F NMR: d = -79.42 ppm; MS
(ESI): m/z = 434 ([M ? H]?); HRMS (ESI): m/z calcd for
C16H11F3INNaO2 ([M ? Na]?) 455.9678, found 455.9662.
NMR (500 MHz, CDCl3 ? DMSO-d6): d = 7.60 (s, 1H),
7.57–7.55 (d, 1H, J = 8.3 Hz), 6.80–6.78 (d, 1H,
J = 8.3 Hz), 4.06 (s, 1H), 3.79–3.73 (m, 1H), 3.60–3.54
(m, 1H), 1.73–1.67 (q, 2H), 0.95 (s, 3H) ppm; 13C NMR
(100 MHz, DMSO-d6): d = 29.6, 110.3, 121.6, 122.2,
124.1, 124.4, 126.3, 128.8, 131.6, 133.0, 144.6, 170.7 ppm;
19F NMR: d = -79.61 ppm; MS (ESI): m/z = 338
([M ? H]?).
3-Hydroxy-1-phenyl-3-(trifluoromethyl)indolin-2-one
(13, C15H10F3NO2)
1
Isolated yield: 80 %; white solid; m.p.: 178–180 °C; H
Acknowledgments P. S. P and V. J. R gratefully acknowledge to
the financial assistance provided by the CSIR, Govt. of India, New
Delhi 12th Five-year plan ORIGIN Project (CSC-0108). RBP (UGC-
SRF), acknowledge for the fellowship provided by UGC, Govt of
India.
NMR (500 MHz, CDCl3 ? DMSO-d6): d = 7.62–7.61 (d,
1H, J = 7.4 Hz), 7.55 (t, 2H), 7.46 (t, 1H), 7.41–7.36 (m,
3H), 7.19 (t, 1H), 6.85–6.83 (d, 1H, J = 7.9 Hz), 3.96 (s,
1H) ppm; 13C NMR (100 MHz, DMSO-d6): d = 110.3,
121.6, 122.2, 124.1, 124.4, 126.3, 127.3, 128.8, 129.5,
129.8, 131.3, 131.6, 133.0, 144.6, 170.7 ppm; 19F NMR:
d = -79.62 ppm; MS (ESI): m/z = 316 ([M ? Na]?);
HRMS (ESI): m/z calcd for C15H10F3NNaO2 ([M ? Na]?)
316.0555, found 316.0539.
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5-Chloro-3-hydroxy-1-(prop-2-yn-1-yl)-3-(trifluo-
romethyl)indolin-2-one (14, C12H7ClF3NO2)
1
Isolated yield: 72 %; white solid; m.p.: 132–134 °C; H
NMR (500 MHz, CDCl3 ? DMSO-d6): d = 7.50 (s, 1H),
7.47–7.45 (d, 1H, J = 8.5 Hz), 7.07–7.06 (d, 1H,
J = 8.3 Hz), 4.50–4.49 (d, 2H, J = 2.2 Hz) 3.90 (s, 1H),
2.30 (t, 1H) ppm; 13C NMR (100 MHz, DMSO-d6):
d = 29.6, 75.0, 75.3, 110.3, 124.1, 126.3, 128.8, 129.8,
131.6,
133.0,
144.6,
170.7 ppm;
19F
NMR:
d = -79.56 ppm; MS (ESI): m/z = 290 ([M ? H]?);
HRMS (ESI): m/z calcd for C12H8ClF3NO2 ([M ? H]?)
258.0316, found 258.0317.
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1-Benzyl-5-bromo-3-hydroxy-3-(trifluoromethyl)indolin-2-
one (15, C16H11BrF3NO2)
1
Isolated yield: 82 %; white solid; m.p.: 138–140 °C; H
´
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Kover WB (2008) J Heterocycl Chem 45:969
NMR (500 MHz, CDCl3 ? DMSO-d6): d = 7.60 (s, 1H),
7.44–7.42 (d, 1H, J = 8.3 Hz), 7.36–7.29 (m, 4H),
7.23–7.22 (d, 1H, J = 6.8 Hz), 6.62–6.60 (d, 1H,
J = 8.3 Hz), 5.07–5.04 (d, 1H, J = 15.7 Hz), 4.75–4.72
(d, 1H, J = 15.7 Hz), 4.30 (s, 1H) ppm; 13C NMR
(100 MHz, DMSO-d6): d = 44.3, 111.6, 116.5, 124.5,
126.9, 127.6, 128.1, 128.5, 129.0, 129.3, 131.6, 133.8,
134.4, 142.5, 171.0 ppm; 19F NMR: d = -79.38 ppm; MS
(ESI): m/z = 386 ([M ? H]?); HRMS (ESI): m/z calcd for
C16H12BrF3NO2 ([M ? H]?) 385.9998, found 385.9984.
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