10.1002/adsc.201800927
Advanced Synthesis & Catalysis
(222 mg, 1.1 mmol) and triphenylphosphine (315 mg, 1.3
mmol) was added to the above reaction mixture. The
reaction mixture was stirred at room temperature and
monitored by TLC. After completion, the mixture was
concentrated in vacuo, and the residue was purified
through silica gel chromatography (PE:EtOAc = 5:1) to
give product 15 (111 mg, 85%, m.p. 88–91 °C) which is a
known compound[26] and the characterization data are in
accordance with the literature; 1H NMR (400 MHz,
CDCl3) δ 8.20 (d, J = 8.0 Hz, 1H), 7.66 (t, J = 7.6 Hz, 1H),
7.54 (d, J = 8.2 Hz, 1H), 7.36 (t, J = 7.6 Hz, 1H), 4.02 (t, J
= 6.0 Hz, 2H), 2.94 (t, J = 6.6 Hz, 2H), 2.01 – 1.93 (m, 2H),
1.93 – 1.85 (m, 2H); 13C NMR (100 MHz, CDCl3) δ 161.2,
153.9, 146.3, 133.2, 125.6, 125.3, 125.1, 119.4, 41.3, 30.9,
21.1, 18.3.
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N-(3-ethynylphenyl)quinazolin-4-amine (16). Quinazolin
-4(3H)-one (3ap) was prepared through the reaction of
formaldehyde, 2-aminobenzamide according to general
procedure A. To an oven-dried 10 mL reaction tube
charged with a stir bar were added 3ap (150 mg, 1.0
mmol), BOP (CAS NO. 56602-33-6, 575 mg, 1.3 mmol,),
3-Aminophenyl-acetylene (140 mg, 1.5 mmol), DMF (2
mL), then DBU (230 mg, 1.5 mmol) was added drop-wise.
The reaction mixture was stirred at 110 °C for 16 h and
then cooled down, 20 mL water was added, the organic
layer was extracted with EtOAc (20 mL) and collected
organic phase was washed with brine (15 mL × 3), dried
over anhydrous Na2SO4, concentrated in vacuo and then
purified through silica gel chromatography (PE:EtOAc =
5:1) to afford the 16 as a pale yellow solid (189 mg, 77%
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1
yield, m.p. 179–181 °C ); H NMR (400 MHz, DMSO-d6)
δ 9.91 (s, 1H), 8.70 (s, 1H), 8.61 (d, J = 8.4 Hz, 1H), 8.15
(s, 1H), 8.02 – 7.97 (m, 1H), 7.93 (t, J = 7.6 Hz, 1H), 7.86
(d, J = 8.4 Hz, 1H), 7.72 (t, J = 7.6 Hz, 1H), 7.47 (t, J = 8.0
Hz, 1H), 7.29 (d, J = 7.6 Hz, 1H), 4.28 (s, 1H); 13C NMR
(100 MHz, DMSO-d6) δ 158.1, 154.8, 150.1, 140.0, 133.6,
129.4, 128.3, 127.2, 126.8, 125.4, 123.4, 123.2, 122.3,
115.6, 84.0, 81.1; IR νmax (neat)/cm-1:3495, 3310, 3212,
2923, 2106, 1621, 1578, 1540, 1442, 1390, 767, 677;
HRMS (ESI/FT-ICR, m/z): calcd for C16H11N3Na+ [M +
Na]+ 268.0845, found. 268.0845.
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Acknowledgements
Financial support from the National Natural Science Foundation
of China (21472053) and the Natural Science Foundation of
Hubei Committee (2016CFA001) is gratefully acknowledged. We
also thank Huazhong University of Science & Technology
Analytical & Testing Center for characterizing new compounds.
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