Arkivoc 2018, v, 0-0
Arafa, W. A. A. et al.
Methylene bis-{2-[(Z)-(5-oxo-2-phenyloxazol-4(5H)-ylidene)methyl]-4,1-phenylene} diacetate (2f).
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Yellow solid, (588 mg, 94%). mp > 400 C. IR (solid, KBr, max, cm-1): 1803, 1736 (C=O), 1654 (C=N), 1597 (C=C).
1H NMR (400 MHz, DMSO): δH 7.93–7.90 (4H, m, 4CH aromatic), 7.66 (2H, s, =CH), 7.59–7.52 (6H, m, 6CH
aromatic), 7.39 (2H, d, J 7.4 Hz, 2CH aromatic), 7.32 (2H, s, 2CH aromatic), 7.01 (2H, d, J 7.4 Hz, 2CH aromatic),
4.03 (2H, s, CH2), 2.42 (6H, s, CH3). MS (ESI) m/z (%): 626.16 (M+, 0.1%), 105 (100). Anal. calc. for C37H26N2O8: C,
70.92; H, 4.18; N, 4.47. Found: C, 71.01; H, 4.11; N, 4.39.
(Z)-4-Benzylidene-2-phenyloxazol-5(4H)-one (9a).38 Yellow solid, (291 mg, 99%). mp 167 oC (lit. mp 166–167).
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IR (solid, KBr, max, cm-1): 1796 (C=O), 1656 (C=N), 1595 (C=C). H NMR (400 MHz, DMSO): δH 8.31 (2H, d, J
7.8 Hz, 2CH aromatic), 8.13 (2H, d, J 7.5 Hz, 2CH aromatic), 7.61 (1H, t, J 7.4, 1CH aromatic), 7.53 (2H, t, J 7.7,
2CH aromatic), 7.51–7.42 (3H, m, 3CH aromatic), 7.32 (1H, s, CH=C). MS (ESI) m/z (%): 294.08 (M+, 69%), 105
(100). Anal. calc. for C16H11NO2: C, 77.10; H, 4.45; N, 5.62. Found: C, 77.17; H, 4.40; N, 5.57.
(Z)-4-(4-Chlorobenzylidene)-2-phenyloxazol-5(4H)-one (9b).39 Yellow solid, (277mg, 98%). mp 204–206 oC (lit.
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mp 203–204). IR (solid, KBr, max, cm-1): 1790 (C=O), 1662 (C=N), 1599 (C=C). H NMR (400 MHz, DMSO): δH:
8.20 (1H, m, 1CH aromatic), 8.17 (1H, d, J 1.5 Hz, 1CH aromatic), 8.15 (1H, d, J 1.7 Hz, 1CH aromatic), 8.14 1H,
(1H, m, 1CH aromatic), 7.64 (1H, m, 1CH aromatic), 7.54 (2H, t, J 7.7 Hz, 2CH aromatic), 7.46 (2H, m, 2CH
aromatic), 7.18 (1H, s, CH=C). MS (ESI) m/z (%): 283.04 (M+, 34%), 103 (100). Anal. calc. for C16H10ClNO2: C,
67.74; H, 3.55; N, 4.94. Found: C, 67.71; H, 3.59; N, 4.89.
o
(Z)-4-(4-Methylbenzylidene)-2-phenyloxazol-5(4H)-one (9c).39 Yellow solid, (260 mg, 99%). mp 143–145 C
(lit. mp 144–145). IR (solid, KBr, max, cm-1): 1788 (C=O), 1641 (C=N), 1603 (C=C). 1H NMR (400 MHz, DMSO): δH
8.19 (2H, dd, J 1.3, 8.2 Hz, 2CH aromatic), 8.10 (2H, d, J 8.2 Hz, 2CH aromatic), 7.58 (1H, dd, J 4.4, 10.7 Hz, 1CH
aromatic), 7.52 (2H, dd, J 7.1, 8.2 Hz, 2CH aromatic), 7.30 (2H, d, J 8.3 Hz, 2CH aromatic), 7.24 (1H, s, CH=C),
2.41 (3H, s, CH3). MS (ESI) m/z (%): 263.09 (M+, 11%), 91 (100). Anal. calc. for C17H13NO2: C, 77.55; H, 4.98; N,
5.32. Found: C, 77.59; H, 4.96; N, 5.28.
(Z)-4-[1-(1-Acetyl-1H-indol-3-yl)ethylidene]-2-phenyloxazol-5(4H)-one (9d). Yellow solid, (333 mg, 97%). mp
312–315 oC. IR (solid, KBr, max, cm-1): 1795, 1712 (C=O), 1655 (C=N), 1605 (C=C). 1H NMR (400 MHz, DMSO): δH
8.34 (1H, s, 1CH aromatic), 8.23 (1H, d, J 7.6 Hz, 1CH aromatic), 8.20–8.17 (2H, m, 2CH aromatic), 7.55–7.51
(4H, m, 4CH aromatic), 7.24–7.21 (2H, m, 2CH aromatic), 2.49 (3H, s, CH3), 2.43 (3H, s, CH3); 13C NMR (100
MHz, CDCl3): δC 169.7 (CO), 167.3 (CO), 161.4, 149.4, 137.5, 136.6, 134.3, 131.4, 129.0, 128.5, 126.4, 125.3,
122.7, 121.9, 121.3, 117.8, 110.3 (C aromatic), 24.5 (CH3), 20.7 (CH3). MS (ESI) m/z (%): 344.11 (M+, 0.8%), 105
(100). Anal. calc. for C21H16N2O3: C, 73.24; H, 4.68; N, 8.13. Found: C, 73.30; H, 4.61; N, 8.06.
(Z)-2-Phenyl-4-[1-(pyridin-4-yl)ethylidene]oxazol-5(4H)-one (9e). Yellow solid, (258 mg, 98%). mp 215–217 oC.
IR (solid, KBr, max, cm-1): 1788 (C=O), 1650 (C=N), 1611 (C=C). 1H NMR (400 MHz, DMSO): δH 8.82–8.80 (2H, m,
2CH aromatic), 8.02–7.99 (2H, m, 2CH aromatic), 7.73–7.71 (2H, m, 2CH aromatic), 7.53–7.50 (3H, m, 3CH
aromatic), 2.54 (3H, s, CH3); 13C NMR (100 MHz, DMSO): δC 167.5 (CO), 161.9, 150.9, 149.2, 142.7, 138.5,
131.1, 128.8, 128.3, 125.9, 121.2 (C aromatic), 21.0 (CH3). MS (ESI) m/z (%): 264.08 (M+, 0.8%), 105 (100). Anal.
calc. for C16H12N2O2: C, 72.72; H, 4.58; N, 10.60. Found: C, 72.68; H, 4.66; N, 10.54.
(Z)-2-Phenyl-4-[1-(pyridin-2-yl)ethylidene]oxazol-5(4H)-one (9f). Yellow solid, (237 mg, 90%). mp 228–231 oC.
IR (solid, KBr, max, cm-1): 1785 (C=O), 1643 (C=N), 1605 (C=C). 1H NMR (400 MHz, DMSO): δH 8.69–8.68 (1H, m,
1CH aromatic), 8.04–8.01 (3H, m, 3CH aromatic), 7.84–7.83 (1H, m, 1CH aromatic), 7.54–7.52 (3H, m, 3CH
aromatic), 7.48–7.47 (1H, m, 1CH aromatic), 2.52 (3H, s, CH3). 13C NMR (100 MHz, DMSO): δC 167.3 (CO),
161.7, 153.6, 149.7, 148.8, 138.9, 136.4, 131.0, 128.6, 128.1, 127.3, 126.1, 121.5 (C aromatic), 24.2 (CH3). MS
(ESI) m/z (%): 264.08 (M+, 2.5), 105 (100). Anal. calc. for C16H12N2O2: C, 72.72; H, 4.58; N, 10.60. Found: C,
72.70; H, 4.62; N, 10.57.
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