Journal of the Iranian Chemical Society
22.3, 42.8, 56.1, 82.4, 91.2, 115.1, 122.0, 124.6, 126.1,
128.7, 129.6, 129.7, 130.7, 136.5, 141.5, 151.5, 157.2; IR
(KBr): 3403, 3032, 2962, 2923, 1578, 1416, 1346, 1212,
1165, 765 cm−1. m/z [M]+: 317.15.
CH of aryl), 7.45–7.50 (m, 2H, CH of aryl), 7.58–7.63 (m,
1H, ArH), 7.72–7.82 (m, 4H, ArH and CH of quinoxaline),
7.89–7.92 (m, 1H, CH of quinoxaline); 13C NMR (75 MHz,
CDCl3): δ 24.4, 25.5, 49.7, 56.4, 85.3, 89.9, 107.4, 118.7,
124.1, 126.2, 126.5, 126.8, 126.9, 127.6, 128.4, 129.4,
129.6, 130.7, 132.5, 134.3, 137.5, 140.6, 155.5, 155.9; IR
(KBr): 3402, 30,045, 2934, 2921, 1611, 1454, 1397, 1245,
1167, 787 cm−1. m/z [M]+: 393.18.
N‑Benzyl‑3‑(3‑phenoxyprop‑1‑ynyl)quinoxa‑
lin‑2‑amine (5c)
1
Yellow powder; mp, 94–95 °C; H NMR (300 MHz,
CDCl3): δ 4.70 (d, J=5.7 Hz, 2H, NHCH2Ph), 5.04 (s, 2H,
CH2OAr), 5.68 (br, 1H, NHCH2Ph), 6.97–7.03 (m, 3H,
ArH), 7.17–7.28 (m, 4H, ArH), 7.39–7.42 (m, 2H, ArH),
7.55–7.61 (m, 3H, ArH and CH of quinoxaline), 7.67–7.70
(m, 1H, CH of quinoxaline), 7.83–7.86 (m, 1H, CH of qui-
noxaline); IR (KBr): 3413, 3056, 2962, 2923, 1610, 1545,
1342, 1189, 1123, 767 cm−1. m/z [M]+: 365.15.
2‑Morpholino‑3‑(3‑(naphthalen‑3‑yloxy)
prop‑1‑ynyl)quinoxaline (5g)
1
yellow powder; mp, 141–142 °C; H NMR (300 MHz,
CDCl3): δ 3.55 (s, 8H, 4CH2), 5.19 (s, 2H, CH2OAr),
7.34–7.41 (m, 2H, ArH), 7.45–7.56 (m, 2H, ArH), 7.63–7.67
(m, 2H, ArH), 7.75–7.84 (m, 4H, ArH and CH of quinox-
aline), 7.92–7.96 (m, 1H, CH of quinoxaline); 13C NMR
(75 MHz, CDCl3): δ 48.8, 56.3, 66.3, 85.1, 90.7, 107.3,
118.6, 124.2, 126.7, 126.8, 126.9, 127.0, 127.8, 128.5,
129.3, 129.8, 130.9, 132.0, 134.2, 137.9, 140.3, 155.0,
155.3; IR (KBr): 3405, 3031, 2934, 2912, 1633, 1419, 1196,
1110, 767 cm−1. m/z [M]+: 395.16.
3‑(3‑(4‑Chlorophenoxy)prop‑1‑ynyl)‑N‑methylqui‑
noxalin‑2‑amine (5d)
yellow powder; mp, 93–94 °C; 1H NMR (300 MHz, CDCl3):
δ 2.77 (d, J=5.1 Hz, 3H, NHCH3), 5.18 (s, 2H, CH2OAr),
5.30 (br, 1H, NHCH3), 7.27–7.30 (m, 1H, ArH), 7.36–7.41
(m, 1H, ArH), 7.43–7.46 (m, 1H, ArH), 7.49–7.60 (m, 1H,
ArH), 7.68–7.71 (m, 1H, ArH), 7.82–7.88 (m, 4H, CH of
quinoxaline); 13C NMR (75 MHz, CDCl3): δ 27.8, 56.3,
82.8, 91.1, 107.9, 118.8, 124.7, 126.8, 127.7, 128.8, 129.7,
134.1, 136.4, 141.5, 152.0, 155.1; IR (KBr): 3401, 3038,
2933, 1612, 1566, 1453, 1203, 1018, 754 cm−1. m/z [M]+:
323.08.
Acknowledgements We gratefully acknowledge the financial support
of the Research Council of the Shahrood University of Technology.
References
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1
yellow powder; mp, 99–100 °C; H NMR (300 MHz,
CDCl3): δ 4.52 (d, J=5.7 Hz, 2H, NHCH2Ph), 5.16 (s, 2H,
CH2OAr), 5.67 (br, 1H, NHCH2Ph), 7.17–7.19 (m, 3H,
ArH), 7.22–7.25 (m, 3H, ArH), 7.34–7.42 (m, 3H, ArH),
7.45–7.50 (m, 1H, ArH), 7.54–7.60 (m, 1H, ArH), 7.65–7.68
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118.6, 124.3, 124.9, 126.3, 126.7, 126.9, 127.2, 127.6,
127.8, 128.5, 128.7, 129.4, 129.5, 129.9, 130.8, 134.2,
136.8, 138.5, 141.3, 151.2, 155.1; IR (KBr): 3404, 3039,
2963, 2914, 1612, 1468, 1204, 1189, 756 cm−1. m/z [M]+:
415.16.
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2‑(3‑(Naphthalen‑3‑yloxy)
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Dark yellow powder; mp, 127–128 °C; 1H NMR (300 MHz,
CDCl3): δ 1.54 (s, 6H, 3CH2), 3.53 (s, 4H, 2CH2), 5.18 (s,
2H, CH2OAr), 7.23–7.27 (m, 1H, ArH), 7.35–7.41 (m, 2H,
1 3