BULLETIN OF THE
Note
KOREAN CHEMICAL SOCIETY
1-Methyl-2-(3-thienyl)-1,8-naphthyridin-4-one (5eh):
Acknowledgments. This research was supported by the
1
m.p. 140–142 ꢀC; H NMR (300 MHz, CDCl3) δ 8.78 (dd,
Duksung
Women's
University
Research
Grants
J = 4.5, 2.0 Hz, 1H), 8.73 (dd, J = 7.9, 2.0 Hz, 1H), 7.54 (dd,
J = 3.0, 1.3 Hz, 1H), 7.50 (dd, J = 4.9, 3.0 Hz, 1H), 7.37 (dd,
J = 7.9, 4.5 Hz, 1H), 7.23 (dd, J = 4.9, 1.3 Hz, 1H), 6.39 (s,
1H), 3.82 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 177.7,
152.1, 151.2, 150.7, 135.8, 135.7, 127.7, 126.9, 126.3,
121.5, 119.6, 113.3, 35.2; FT-IR (KBr) 1621 (C O) cm−1;
MS m/z (%) 242 (M+, 100).
3000002203 (2014).
References
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1-Ethyl-2-(3-pyridyl)-1,8-naphthyridin-4-one (5fi): m.
1
p. 112–113 ꢀC; H NMR (300 MHz, CDCl3) δ 8.78–8.82
(m, 2H), 8.73–8.77 (m, 2H), 7.79–7.84 (m, 1H), 7.50 (ddd,
J = 7.8, 4.9, 0.7 Hz, 1H), 7.40 (dd, J = 7.9, 4.5 Hz, 1H), 6.25
(s, 1H), 4.37 (q, J = 7.0 Hz, 2H), 1.24 (t, J = 7.0 Hz, 3H);
13C NMR (75 MHz, CDCl3) δ 177.4, 152.3, 151.6, 150.8,
150.4, 148.6, 135.9, 135.6, 131.7, 123.3, 121.8, 119.9,
114.2, 42.0, 14.8; FT-IR (KBr) 1625 (C O) cm−1; MS m/z
(%) 251 (M+, 79), 250 (100).
1-Methyl-2-(40-chlorophenyl)-2,3-dihydro-1,8-naphthyri-
din-4-one (8kh): viscous liquid; 1H NMR (300 MHz, CDCl3)
δ 8.39 (dd, J = 4.8, 2.0 Hz, 1H), 8.00 (dd, J = 7.6, 2.0 Hz, 1H),
7.26 (d, J = 8.4 Hz, 2H), 7.05 (d, J = 8.4 Hz, 2H), 6.67 (dd, J =
7.6, 4.8 Hz, 1H), 4.75 (dd, J = 6.3, 5.0 Hz, 1H), 3.20 (dd, J =
16.1, 6.6 Hz, 1H), 3.16 (s, 3H), 2.87 (dd, J = 16.1, 4.8 Hz, 1H);
13C NMR (75 MHz, CDCl3) δ 192.0, 159.3, 155.0, 137.6,
135.7, 133.8, 129.3, 127.7, 114.6, 113.0, 61.6, 44.6, 35.6;
FT-IR (film) 1681 (C O) cm−1; MS m/z (%) 274 (M++2,
31), 272 (M+, 94), 161 (100).
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1-Ethyl-2-(20-methoxyphenyl)-2,3-dihydro-1,8-naphthyr-
idin-4-one (8li): m.p. 127–128 ꢀC; 1H NMR (300 MHz,
CD3COCD3) δ 8.38 (dd, J = 4.7, 2.0 Hz, 1H), 7.88 (dd, J =
7.5, 2.0 Hz, 1H), 7.21–7.27 (m, 1H), 7.04 (d, J = 8.3 Hz,
1H), 6.74–6.81 (m, 2H), 6.67 (dd, J = 7.5, 4.7 Hz, 1H), 5.28
(dd, J = 7.2, 2.7 Hz, 1H), 4.21–4.32 (m, 1H), 3.90 (s, 3H),
3.16 (dd, J = 16.1, 7.3 Hz, 1H), 2.99–3.10 (m, 1H), 2.88
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134.7, 128.9, 127.1, 126.2, 120.2, 114.1, 111.9, 111.3,
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cm−1; MS m/z (%) 282 (M+, 92), 119 (100).
1-Methyl-2-(2-furyl)-2,3-dihydro-1,8-naphthyridin-4-
one (8mh): m.p. 107–109 ꢀC; 1H NMR (300 MHz, CDCl3) δ
8.34 (dd, J = 4.8, 2.0 Hz, 1H), 8.04 (dd, J = 7.6, 2.0 Hz, 1H),
7.31 (d, J = 1.7 Hz, 1H), 6.65 (dd, J = 7.7, 4.8 Hz, 1H), 6.24
(dd, J = 3.3, 1.8 Hz, 1H), 6.07 (d, J = 3.3 Hz, 1H), 4.79 (dd,
J = 6.3, 3.3 Hz, 1H), 3.27 (s, 3H), 3.16 (dd, J = 16.4, 6.4 Hz,
1H), 3.01 (dd, J = 16.4, 3.3 Hz, 1H); 13C NMR (75 MHz,
CDCl3) δ 192.4, 158.6, 154.5, 152.0, 142.7, 135.6, 114.6,
113.1, 110.1, 107.6, 56.2, 41.3, 35.8; FT-IR (KBr) 1682
(C O) cm−1; MS m/z (%) 228 (M+, 100).
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Bull. Korean Chem. Soc. 2015, Vol. 36, 1908–1911
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