1114
N. H. Naik et al.
singlet, broad singlet, doublet, triplet, and multiplet, respectively.
Mass spectra (MS) were recorded on a PerkinElmer Clarus500
instrument. High resolution MS were obtained on a Micromass
Q-TOF apparatus. Gas chromatography-mass spectrometry
(GCMS) electron impact (EI) data were obtained on a
PerkinElmer Clarus500 instrument at 70 eV.
vacuum and purification by column chromatography (1 : 9, ethyl
acetate : hexane) provided bouchardatine (1) as an off white solid
(0.55 g, 68%). Mp: 255 ꢀ2578C (lit. . 2608C[3]). nmax(ATR)/
cmꢀ1 3051, 2922, 2852, 1693, 1665, 1607, 1572, 1437, 1188.
1H NMR (300MHz, [D6]DMSO) d 7.17 ꢀ7.2 (m, 2H, ArH), 7.35
(t, 1H, J 7.1 Hz, ArH), 7.60–7.65 (m, 2H, ArH), 7.83 (d, 1H,
J 7.1 Hz, ArH), 8.01 (m, 2H, ArH), 10.13 (s, 1H, CHO), 11.69
(s, 1H, NH), 12.35 (s, 1H, NH). 13C NMR (75 MHz, [D6]DMSO)
d 184.1, 166.5, 160.4, 142.7, 138.5, 135.8, 133.2, 129.5, 129.0,
124.8, 124.4, 123.8, 123.4, 122.8, 120.2, 118.5, 112.5. m/z (EI)
289 [3%, (M)þꢂ], 261 (2), 144 (100), 130 (20), 102 (30), 76 (20).
Synthesis
2-(((1-(Phenylsulfonyl)-1H-indol-2-yl)methylene)amino)
benzamide 6
To a solution of N-protected indole-2-carbaldehyde (0.5 g,
1.7 mmol) in acetic acid (5 mL) was added anthranilamide
(0.2 g, 1.7 mmol) at room temperature. The mixture was then
heated at 808C for 30 min. Product was filtered and washed with
excess water to give imine 6 (0.67 g, 95 %) as a white solid. Mp
258–2608C. nmax(ATR)/cmꢀ1 3371, 3226, 1653, 1607, 1498,
Supplementary Material
1
The H and 13C NMR spectra of compounds 6, 7 and 1 are
available on the Journal’s website.
1
Acknowledgements
1366. H NMR (300 MHz, [D6]DMSO) d 6.53 (s, 1H, CH),
6.67–6.71 (m, 2H, NH), 6.89 (d, 1H, J 8.1 Hz, ArH), 7.10 (s, 1H,
ArH), 7.15–7.32 (m, 3H, ArH), 7.51–7.57 (m, 3H, ArH),
7.64–7.69 (m, 2H, ArH), 7.88–7.96 (m, 3H, ArH), 8.42 (s, 1H,
NH). 13C NMR (75 MHz, [D6]DMSO) d 163.2, 145.6, 141.4,
136.6, 136.5, 134.6, 133.4, 129.6, 128.5, 127.1, 126.4, 125.2,
124.1, 121.6, 117.5, 115.3, 114.5, 114.3, 111.6. m/z (HR-MSESI)
404.1075; [MþH]þ requires 404.10689.
We are grateful to Mrs. J. P. Choudhary and Ms. Sheetal for NMR spectra
and Mr. Yogesh for IR spectra.
References
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2-(1H-Indol-2-yl)quinazolin-4(3H)-one 7
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2-(4-Oxo-3,4-dihydroquinazolin-2-yl)-1H-indole-3-
carbaldehyde 1
2-Chloro-1H-indole-3-carbaldehyde 14 (0.5 g, 2.7 mmol)
and quinazolin-4(3H)-one 15 (0.4 g, 2.7 mmol) in dry DMF
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