S. Chikhalikar, V. Bhawe, M. Jachak, M. Ghagare
FULL PAPER
142.9, 139.2, 129.3, 129.2, 127.9 (2ϫ C), 126.9 (2ϫ C), 116.2, 89.9,
30.5 ppm. C14H10N2O2 (238.25): calcd. C 70.58, H 4.23, N 11.76;
found C 70.56, H 4.07, N 11.73.
Acknowledgments
We gratefully acknowledge financial support for this project from
the University Grants Commission (UGC), New Delhi, India. We
thank Mamta Joshi (National Facility for High-Field NMR,
T. I. F. R. Mumbai) for 2D ROESY NMR spectroscopy assistance.
We also acknowledge support and facilities provided by Bhavans
and K. T. H. M. Colleges MS India.
5-Acetyl-1-(4-chlorophenyl)-6-oxo-1,6-dihydropyridine-3-carbonitrile
(5b): White solid; m.p. 153–154 °C. MS (EI, methanol): m/z = 272,
257, 243, 229, 215, 194, 166, 139, 111, 75. FTIR (KBr): ν = 3070,
˜
2238, 1694, 1683, 1517, 1224, 1096, 839 cm–1. 1H NMR
(499.85 MHz, TMS, [D6]DMSO): δ = 8.86 (d, J = 2.9 Hz, 1 H),
8.20 (d, J = 2.8 Hz, 1 H), 7.61 (d, J = 8.3 Hz, 2 H), 7.54 (d, J =
8.3 Hz, 2 H), 2.49 (s, 3 H) ppm. 13C NMR (125.70 MHz, [D6]-
DMSO): δ = 195.5, 159.0, 151.5, 143.0, 137.9, 133.9, 129.2 (2ϫ C),
128.9 (2ϫ C), 127.9, 116.1, 90.0, 30.3 ppm. C14H9ClN2O2 (272.69):
calcd. C 61.66, H 3.33, N 10.27; found C 61.68, H 3.01, N 10.08.
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5-Acetyl-1-(2,3-dimethylphenyl)-6-oxo-1,6-dihydropyridine-3-carbo-
nitrile (5c): White solid; m.p. 148–152 °C. MS (EI, methanol): m/z
= 266, 247, 232, 223, 209, 195, 179, 153, 131, 117, 103, 91, 77.
FTIR (KBr): ν = 3070, 2920, 2233, 1683, 1669, 1279, 1517, 925,
˜
786, 586 cm–1. 1H NMR (499.85 MHz, TMS, [D6]DMSO): δ = 8.79
(d, J = 2.4 Hz, 1 H), 8.25 (d, J = 2.4 Hz, 1 H), 7.33 (d, J = 7.4 Hz,
1 H), 7.26 (t, J = 7.3, J = 7.5 Hz, 1 H), 7.19 (d, J = 7.3 Hz, 1 H),
2.50 (s, 3 H), 2.31 (s, 3 H), 1.93 (s, 3 H) ppm. 13C NMR
(125.70 MHz, [D6]DMSO): δ = 195.5, 158.8, 151.6, 143.1, 138.6,
137.9, 133.0, 130.8, 127.8, 126.4, 124.9, 116.1, 90.1, 30.3, 19.8,
13.8 ppm. C16H14N2O2 (266.30): calcd. C 72.16, H 5.30, N 10.52;
found C 72.51, H 5.35, N 10.44.
5-Acetyl-1-(2,4-dimethylphenyl)-6-oxo-1,6-dihydropyridine-3-carbo-
nitrile (5d): Off-white solid; m.p. 213–217 °C. MS (EI, methanol):
m/z = 266, 247, 232, 223, 195, 179, 151, 132, 121, 109, 91, 77, 67.
FTIR (KBr): ν = 3009, 2226, 1683, 1657, 1544, 1266, 895, 836 cm–1.
˜
1H NMR (499.85 MHz, TMS, CDCl3): δ = 7.91 (d, J = 2.6 Hz, 1
H), 7.19 (d, J = 2.5 Hz, 1 H), 6.94 (s, 2 H), 6.21 (s, 1 H), 2.80 (s,
3 H), 2.28 (s, 3 H), 2.26 (s, 3 H) ppm. 13C NMR (125.70 MHz,
CDCl3): δ = 198.2, 159.82, 149.8, 146.2, 134.3, 134.1, 131.2, 128.9,
127.1, 122.4, 117.1, 114.9, 94.2, 21.7, 21.0, 18.5 ppm. C16H14N2O2
(266.30): calcd. C 72.16, H 5.30, N 10.52; found C 71.91, H 5.35,
N 10.24.
5-Acetyl-1-(2,4-dichlorophenyl)-6-oxo-1,6-dihydropyridine-3-carbo-
nitrile (5e): Off-white solid; m.p. 118–123 °C. MS (EI, methanol):
m/z = 306, 294, 290, 276, 229, 168, 161, 151, 133, 124, 109, 85, 67.
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FTIR (KBr): ν = 3086, 2232, 1680, 1668, 1520, 1392, 1227, 861,
˜
1
846 cm–1. H NMR (499.85 MHz, TMS, [D6]DMSO): δ = 8.78 (s,
1 H), 8.21 (s, 1 H), 7.72 (d, J = 7.3 Hz, 1 H), 7.32 (s, 1 H), 7.31 (d,
J = 7.3 Hz, 1 H), 2.35 (s, 3 H) ppm. 13C NMR (125.70 MHz, [D6]
DMSO): δ = 196.3, 148.3, 156.5, 137.8, 135.7, 135.5, 134.1, 131.3,
130.8, 124.7, 120.1, 116.0, 89.9, 25.6 ppm. C14H8Cl2N2O2 (307.14):
calcd. C 54.75, H 2.63, N 9.12; found C 54.89, H 2.34, N 8.86.
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5-Acetyl-6-oxo-1-(o-tolyl)-1,6-dihydropyridine-3-carbonitrile
(5f):
White solid; m.p. 133–135 °C. MS (EI, methanol): m/z = 253, 251,
226, 209, 191, 169, 158, 151, 133, 118, 107, 91, 77. FTIR (KBr): ν
˜
= 3056, 2231, 1694, 1669, 1514, 1370, 1281, 976, 759, 592 cm–1. 1H
NMR (499.85 MHz, TMS, [D6]DMSO): δ = 8.30 (d, J = 2.5 Hz, 1
H), 7.97 (d, J = 2.4 Hz, 1 H), 7.44 (t, J = 6.1, J = 1.9 Hz,1 H),
7.40 (q, J = 6.1, J = 6.1, J = 1.2 Hz, 2 H), 7.18 (t, J = 6.7, J =
1.2 Hz, 1 H) ppm. 13C NMR (125.70 MHz, [D6]DMSO): δ = 192.3,
153.7, 143.6, 138.2, 131.8, 129.5, 127.9, 126.8, 124.2, 122.4, 121.6,
114.5, 86.4, 31.0, 17.7 ppm. C15H12N2O2 (252.27): calcd. C 71.42,
H 4.79, N 11.10; found C 71.74, H 4.61, N 10.85.
Supporting Information (see footnote on the first page of this arti-
cle): 1H and 13C NMR spectra for 2, 3, and 5. 2D ROESY spectra
for 3c.
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