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P.A. Conway et al. / Tetrahedron 65 (2009) 2935–2938
(t, J¼7.7, 2H), 6.68 (t, J¼7.9, 1H), 2.70 (m, 2H), 1.20 (t, J¼7.6, 3H); 13
C
3H), 6.41–6.34 (m, 4H), 3.79 (s, 3H); 13C NMR (101 MHz, CDCl3)
34.2, 111.1, 111.6, 118.8, 121.1, 121.2, 124.6, 126.2, 127.2, 127.5, 127.8,
NMR (126 MHz, CDCl3)
d
12.9, 22.2, 125.7, 128.1, 128.8, 133.0, 135.7,
d
141.0, 162.6, 166.2; IR (KBr) 3069.65, 2964.07, 2837.48, 1798.78,
1748.64, 1673.91, 1559.19, 876.49, 849.97, 779.10 cmꢂ1. Anal. Calcd
for C12H11NO2: C, 71.63; H, 5.51; N, 6.96. Found: C, 71.85; H, 5.65; N,
6.74.
128.8, 128.9, 129.0, 129.7, 132.0, 132.4, 161.0, 168.2; IR (KBr) 3481.38,
3429.31, 3379.64, 1759.73, 1643.06, 1556.28, 1486.37, 1416.95,
1383.68, 866.85, 729.92 cmꢂ1. Anal. Calcd for C15H12N2O2: C, 71.42;
H, 4.79; N, 11.10. Found: C, 71.65; H, 4.82; N, 11.25.
4.3.11. 4-Cyclohex-3-enylmethylene-2-phenyloxazol-5-one (13)
4.3.17. 2-Phenyl-4-(4-pyridinyl)-5-oxazolone (19)
White powder, 33%, mp 109–110 ꢀC (lit. mp 109–110).20 1H NMR
Beige powder, 45%, mp 168–169 ꢀC (lit. mp 168).24 1H NMR
(500 MHz, CDCl3)
d
8.09 (d, J¼8.0, 2H), 7.58 (t, J¼7.4, 1H), 7.49
(400 MHz, CDCl3)
d
8.76 (d, J¼5.5, 2H), 8.21 (d, J¼7.3, 2H), 8.01
(t, J¼7.7, 2H), 6.64 (d, J¼9.9, 1H), 5.82–5.67 (m, 2H), 3.38–3.27
(m, 1H), 2.26 (t, J¼14.8, 1H), 2.22–2.13 (m, 2H), 2.09–1.99 (m, 1H),
1.94–1.85 (m, 1H), 1.72–1.60 (m, 1H); 13C NMR (101 MHz, CDCl3)
(d, J¼5.8, 2H), 7.67 (t, J¼7.4, 1H), 7.57 (t, J¼7.6, 2H), 7.13 (s, 1H); 13C
NMR (101 MHz, CDCl3) d 125.0, 125.1, 127.7, 128.8, 129.1, 134.2, 137.1,
140.1, 150.5, 165.5, 166.5; IR (KBr) 3440.88, 3385.44, 1797.82,
1768.89, 1657.04, 1591.95, 1559.17, 868.29, 814.78 cmꢂ1. Anal. Calcd
for C15H10N2O2: C, 71.99; H, 4.03; N, 11.19. Found: C, 72.14; H, 4.21;
N, 11.04.
d
24.1, 27.9, 30.5, 34.0, 125.2, 125.9, 127.3, 128.4, 129.1, 133.3, 135.4,
143.7, 162.9, 166.7; IR (KBr) 3025.78, 2976.52, 2913.93, 2845.26,
2834.86, 1805.53, 1671.02, 1605.44, 1568.33, 1491.67, 1453.10,
878.42, 861.00, 842.74, 781.03 cmꢂ1. Anal. Calcd for C16H15NO2: C,
75.87; H, 5.97; N, 5.53. Found: C, 76.02; H, 5.84; N, 5.72.
4.3.18. 4-(Furan-3-ylmethylene)-2-phenyloxazol-5(4H)-one (20)
Pale yellow powder, 66%, mp 195–197 ꢀC. 1H NMR (500 MHz,
4.3.12. 4-(But-2-enylidene)-2-phenyloxazol-5-one (14)
CDCl3)
d
8.14 (d, J¼7.6, 2H), 8.11 (s, 1H), 7.60 (t, J¼7.3, 1H), 7.52
White powder, 49%, mp 154–156 ꢀC (lit. mp 154).15 1H NMR
(t, J¼7.5, 3H), 7.20 (s, 1H); 13C NMR (126 MHz, CDCl3)
d 110.0, 111.1,
(400 MHz, CDCl3)
J¼9.7, 5.3, 2H), 6.97 (d, 1H), 6.52–6.37 (m, 1H), 2.02 (d, J¼7.1, 3H);
13C NMR (101 MHz, CDCl3)
19.4, 127.3, 128.0, 128.8, 132.5, 132.9,
d
8.14–8.06 (m, 2H), 7.61–7.55 (m, 1H), 7.49 (dd,
117.9, 121.4, 122.8, 125.7, 128.2, 128.9, 132.8, 133.1, 144.3, 147.8; IR
(KBr) 3447.63, 3422.56, 1793.00, 1655.11, 1554.83, 1490.23, 858.17,
803.21, 754.28 cmꢂ1. Anal. Calcd for C14H9NO3: C, 70.29; H, 3.79; N,
5.86. Found: C, 70.37; H, 3.65; N, 5.87.
d
133.2, 144.2, 145.5, 161.9, 167.0; IR (KBr) 3034.94, 2962.14, 2938.03,
2913.44, 1789.14, 1762.14, 1654.63, 1556.76, 1449.73, 977.25, 882.27,
860.58, 780.37 cmꢂ1. Anal. Calcd for C13H11NO2 requires: C, 73.23;
H, 5.20; N, 6.57. Found: C, 73.31; H, 5.27; N, 6.48.
Acknowledgements
We would like to thank Prof. Patrick Guiry for the use of his
microwave. We are grateful to Science Foundation Ireland for
funding this project.
4.3.13. 4-(3-Methylbut-2-enylidene)-2-phenyloxazol-5-one (15)
Bright yellow solid, 61%, mp 113–114 ꢀC. 1H NMR (400 MHz,
CDCl3)
d
8.10 (d, J¼7.2, 2H), 7.56 (dd, J¼10.4, 4.3, 1H), 7.49 (t, J¼7.4,
2H), 7.26 (d, J¼3.6, 1H), 6.84 (d, J¼12.2, 1H), 2.04 (d, J¼10.9, 6H); 13C
NMR (101 MHz, CDCl3)
d 19.5, 27.3, 121.6, 125.9, 127.9, 128.8, 129.4,
References and notes
132.0, 132.8, 152.7, 161.5, 167.4; IR (KBr) 3056.15, 2970.33, 2910.55,
2850.77, 1783.36, 1664.99, 1589.28, 1448.76, 871.67, 774.28 cmꢂ1
.
1. Erlenmeyer, E. Annalen. 1893, 275, 1–12.
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Kingston, G. I. D. J. Nat. Prod. 1986, 49, 626–630.
Anal. Calcd for C14H13NO2: C, 73.99; H, 5.77; N, 6.16. Found: C, 74.18;
H, 5.82; N, 6.08.
4. (a) Bakos, J.; Neil, B.; Toros, S.; Eifert, G.; Bihari, F.; Nagy, M.; Saros, L.; Durko,
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3447–3453.
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11. Mogilaiah, K.; Prashanthi, M.; Reddy, S. C. Indian J. Chem. 2003, 42B, 2126–2128.
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cock, C. H., Eds.; Peragmon: Oxford, 1991; Vol. 2, pp 402–407, and references
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14. Kitazawa, M.; Higuchi, R.; Takahashi, M.; Wada, T.; Sasabe, H. J. Phys. Chem.
1995, 99, 14784–14792.
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4.3.14. 2-Phenyl-4-(2-thiophenyl)-5-oxazolone (16)
Bright yellow solid, 70%, mp 174–175 ꢀC (lit. mp 175).21 1H NMR
(500 MHz, CDCl3)
d
8.20–8.14 (m, 2H), 7.72 (d, J¼5.1, 1H), 7.63
(d, J¼3.7, 1H), 7.62–7.58 (m, 1H), 7.52 (t, J¼7.6, 2H), 7.48 (s, 1H), 7.16
(dd, J¼5.0, 3.8, 1H); 13C NMR (101 MHz, CDCl3)
d 124.8, 125.6, 127.9,
128.3, 128.9, 130.9, 133.1, 134.9, 135.3, 137.6, 162.5, 166.9; IR (KBr)
3445.71, 3424.01, 1791.55, 1770.82, 1643.54, 1554.35, 1415.02,
855.76, 783.56 cmꢂ1. Anal. Calcd for C14H9NO2S: C, 65.87, H, 3.55, N,
5.49, S, 12.56. Found: C, 65.64, H, 3.66, N, 5.40, S, 12.40.
4.3.15. 2-Phenyl-4-(2-furanyl)-5-oxazolone (17)
Bright yellow powder, 71%, mp 175–176 ꢀC (lit. mp 175).22 1H
NMR (300 MHz, CDCl3)
d
8.19–8.14 (m, 1H), 7.69 (d, J¼1.2, 1H), 7.60
(dd, J¼14.1, 5.5, 2H), 7.51 (dd, J¼18.0, 11.0, 2H), 7.26 (s, 1H), 7.19
(s, 1H), 6.66 (dd, J¼3.3, 1.5, 1H); 13C NMR (101 MHz, CDCl3)
d 113.7,
118.3, 120.1, 125.6, 127.7, 128.3, 128.9, 130.4, 133.2, 146.6, 150.5,
167.1; IR (KBr) 3482.35, 3410.99, 1789.62, 1654.15, 1559.19, 1557.24,
1492.16, 1465.16, 883.56, 861.06, 757.41 cmꢂ1. Anal. Calcd for
C14H9NO3: C, 70.29; H, 3.79; N, 5.86. Found: C, 70.46; H, 3.82; N,
5.62.
16. Rao, Y. S. J. Org. Chem. 1976, 41, 722–725.
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23. Cativiela, C. An. Quim., Ser. C 1985, 81, 56–61.
4.3.16. 2-Phenyl-4-(N-methylpyrrolo)-5-oxazolone (18)
Dark yellow powder, 45%, mp 185–186 ꢀC (lit. mp 185–186).23 1H
NMR (400 MHz, CDCl3)
d
8.16–8.11 (m, 6H), 7.74 (dd, J¼4.1, 1.2, 3H),
7.56–7.53 (m,1H), 7.51 (dd, J¼6.2,1.4, 2H), 7.18 (s, 3H), 6.94–6.90 (m,
24. Slater, G. Tetrahedron 1966, 22, 35–42.