Skip to main content

Table 2 Chemical structures, spectra data, and yields of the final synthesized of 1,3-naphtoxazines

From: Efficient synthesis of 1,3-naphtoxazine derivatives using reusable magnetic catalyst (GO-Fe3O4–Ti(IV)): anticonvulsant evaluation and computational studies

Entry Chemical name Spectra data Yield (%)
S1 2-(4-bromophenyl)-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine White solid, m.p. 116–118 °C. FT-IR (ATR) ῡ (cm−1): 1588, 1489, 1223, 1092. 1H NMR (Acetone-d6, 400 MHz) δ ppm: 7.84 (t, 2H, J = 9.2 Hz, Ar–H), 7.71 (d, 1H, J = 9.2 Hz, Ar–H), 7.52 (t, 1H, J = 8.4 Hz, Ar–H), 7.37–7.40 (m, 3H, Ar–H), 7.20 (d, 2H, J = 9.2 Hz, Ar–H), 7.01 (d, 1H, J = 9.2 Hz, Ar–H), 5.51 (s, 2H, O–CH2–N), 5.03 (s, 2H, –Ar–CH2–N) 95
S2 2-benzyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine Off-white, m.p. 125–127 °C. FT-IR (ATR) ῡ (cm−1): 1623, 1597, 1461, 1223, 1058, 738. 1H NMR (DMSO-d6, 500 MHz) δ ppm: 7.05–7.71 (m, 11H, Ar–H), 4.89 (s, 2H, O–CH2–N), 4.22 (s, 2H, –Ar–CH2–N), 3.89 (s, 2H, –Ar–CH2–N). 13C NMR (DMSO-d6, 100 MHz) δ ppm: 46.5, 55.2, 81.5, 111.7, 118.3, 121.1, 123.4, 126.6, 127.2, 127.8, 128.3, 128.4, 128.5, 128.6, 131.5, 138.3, 151.4 94
S3 2-cyclohexyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine Off-white solid, m.p. 248 °C (d). FT-IR (ATR) ῡ (cm−1): 2926, 2852, 1597, 1467, 1227, 1058. 1H NMR (DMSO-d6, 500 MHz) δ ppm: 7.66–7.81 (m, 3H, Ar–H), 7.48 (m, 1H, Ar–H), 7.35 (m, 1H, Ar–H), 6.98 (m, 1H, Ar–H), 4.99 (s, 2H, O–CH2–N), 4.33 (s, 2H, –Ar–CH2–N), 2.70 (m, 1H, CH–N), 1.08–1.86 (m, 10H, 5CH2) 92
S4 2-phenethyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine White solid, m.p. 232 °C (d). FT-IR (ATR) ῡ (cm−1): 1597, 1469, 1225, 1060. 1H NMR (DMSO-d6, 500 MHz) δ ppm: 7.81 (m, 1H, Ar–H), 7.69 (m, 2H, Ar–H), 7.49 (m, 1H, Ar–H), 7.35 (m, 1H, Ar–H), 7.24 (m, 5H, Ar–H), 7.02 (m, 1H, Ar–H), 4.92 (s, 2H, O-CH2-N), 4.32 (s, 2H, –Ar–CH2–N), 2.96 (m, 2H, Ar–CH2CH2–N), 2.88 (m, 2H, Ar–CH2–CH2–N). 13C NMR (DMSO-d6, 125 MHz) δ ppm: 34.9, 47.9, 54.0, 82.7, 113.1, 119.2, 122.3, 124.2, 126.7, 127.3, 128.5, 129.1, 129.2, 129.3, 129.5, 132.4, 140.9, 152.4 92
S5 2-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine White solid, m.p. 47–49 °C FT-IR (ATR) ῡ (cm−1): 3060, 1600, 1496, 1231, 1057; 1H NMR (Acetone-d6, 400 MHz) δ ppm: 7.89 (d, 1H, J = 8.4 Hz, Ar–H), 7.85 (d, 1H, J = 8 Hz, Ar–H), 7.73 (d, 1H, J = 9.2 Hz, Ar–H), 7.53–7.57 (m, 1H, Ar–H), 7.38–7.42 (m, 1H, Ar–H), 7.23–7.28 (m, 4H, Ar–H), 7.04 (d, 1H, J = 8.8 Hz, Ar–H), 6.87–6.91 (m, 1H, Ar–H), 5.54 (s, 2H, O–CH2–N), 5.06 (s, 2H, –Ar–CH2–N) 91
S6 2-hexyl-2,3,4a,10b-tetrahydro-1H-naphtho[1,2-e][1,3]oxazine Brown solid, m.p. 177 °C (d). FT-IR (ATR) ῡ (cm−1): 2927, 2854, 1597, 1467, 1225, 1057. 1H NMR (DMSO-d6, 500 MHz) δ ppm: 7.80 (m, 1H, Ar–H), 7.68 (m, 2H, Ar–H), 7.47 (m, 1H, Ar–H), 7.34 (m, 1H, Ar–H), 7.00 (m, 1H, Ar–H), 4.87 (s, 2H, O–CH2–N), 4.25 (s, 2H, –Ar–CH2–N), 2.68 (m, 2H, –CH2–N), 1.53 (m, 2H, CH2), 1.25 (m, 6H, 3CH2), 0.84 (m, 3H, CH3). 13C NMR (DMSO-d6, 125 MHz) δ ppm: 14.8, 23.0, 27.2, 28.4, 32.0, 47.9, 52.1, 82.7, 113.0, 119.1, 122.2, 124.1, 127.3, 128.5, 129.2, 129.3, 132.4, 152.4 91
S7 2-(p-tolyl)-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine Yellow solid, m.p. 87–89 °C. FT-IR (ATR) ῡ (cm−1): 1597, 1470, 1226, 1096. 1H NMR (Acetone-d6, 400 MHz) δ ppm: 7.82 (t, 2H, J = 8.8 Hz, Ar–H), 7.69 (d, 1H, J = 9.2 Hz, Ar–H), 7.51 (t, 1H, J = 8 Hz, Ar–H), 7.36 (t, 1H, J = 8 Hz, Ar–H), 6.99–7.04 (m, 3H, Ar–H), 7.09–7.11 (m, 2H, Ar–H), 5.52 (s, 2H, O–CH2–N), 5.02 (s, 2H, –Ar–CH2–N), 2.24 (s, 3H, CH3–Ar) 94
S8 2-(2-chlorobenzyl)-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine Yellow soid, m.p. 70–75 °C. FT-IR (ATR) ῡ (cm−1): 1594, 1468, 1226, 1057. 1H NMR (DMSO-d6, 500 MHz) δ ppm: 7.07–7.82 (m, 10H, Ar–H), 4.95 (s, 2H, O–CH2–N), 4.27 (s, 2H, –Ar–CH2–N), 4.00 (s, 2H, –Ar–CH2–N). 13C NMR (DMSO-d6, 100 MHz) δ ppm: 46.8, 52.6, 82.0, 111.7, 118.3, 121.3, 123.4, 126.5, 127.2, 127.8, 128.4, 128.5, 128.9, 129.35, 130.6, 131.5, 133.2, 135.8, 151.4 85
S9 2-(furan-2-ylmethyl)-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine Pale-pink, m.p. 98–100 °C. FT-IR (ATR) ῡ (cm−1): 1597, 1467, 1226, 1060. 1H NMR (DMSO-d6, 500 MHz) δ ppm: 7.71–8.02 (m, 4H, Ar–H), 7.36–7.61 (m, 2H, Ar–H), 7.04 (s, 1H, Ar–H), 6.32–6.52 (m, 2H, Ar–H), 4.89 (s, 2H, O–CH2–N), 4.26 (s, 2H, –Ar–CH2–N), 3.90 (s, 2H, furan-CH2–N). 13C NMR (DMSO-d6, 125 MHz) δ ppm: 46.4, 47.9, 81.2, 108.8, 110.4, 111.5, 118.3, 121.2, 123.4, 126.6, 127.8, 128.4, 128.5, 131.48, 142.7, 151.3, 151.8 90
S10 2-(4-ethylphenyl)-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine Off-white solid, m.p. 43–46 °C. FT-IR (ATR) ῡ (cm−1): 1597, 1467, 1226, 1056. 1H NMR (Acetone-d6, 400 MHz) δ ppm: 7.80–7.85 (m, 2H, Ar–H), 7.69–7.71 (m, 1H, Ar–H), 7.50–7.55 (m, 1H, Ar–H), 7.35–7.40 (m, 1H, Ar–H), 6.99–7.14 (m, 5H, Ar–H), 5.49 (s, 2H, O-CH2-N), 5.00 (s, 2H, -Ar-CH2-N), 2.49–2.54 (m, 2H, –CH2–CH3), 1.15 (t, 3H, J = 7 Hz, –CH2CH3) 89
S11 2-(4-methoxyphenyl)-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine Off-white solid, m.p. 76–78 °C FT-IR (ATR) ῡ (cm−1): 1596, 1467, 1246, 1230, 1031. 1H NMR (Acetone-d6, 400 MHz) /δ ppm: 7.80–7.82 (m, 2H, Ar–H), 7.70 (d, 1H, J = 8.8 Hz, Ar–H), 7.51 (m, 1H, Ar–H), 7.36 (m, 1H, Ar–H), 7.13 (d, 2H, J = 7.2 Hz, Ar–H), 7.00 (d, 1H, J = 8.8 Hz, Ar–H), 6.80 (d, 2H, J = 7.2 Hz, Ar–H), 5.42 (s, 2H, O-CH2-N), 4.93 (s, 2H, -Ar-CH2-N), 3.68 (s, 3H, O-CH3) 92