10176
Y. A. Ibrahim et al. / Tetrahedron 57 ,2001) 10171±10176
6d, MS: m/z211 (M1); IR (KBr): 3265, 1660.
6e, MS: m/z227 (M1); IR (KBr): 3350, 1650.
research grant no. SC091 and the facilities of ANALAB and
SAF are gratefully acknowledged.
6f, MS: m/z187 (M1); IR (KBr): 1650; 1H NMR (CDCl3):
d 6.56 (s, 1H), 7.2±7.66 (m, 6H), 8.06 (s, 1H), 9.70 (br s,
1H).
References
1. Al-Awadi, N. A.; Elnagdi, M. H.; Ibrahim, Y. A.; Kaul, K.;
Kumar, A. Tetrahedron 2001, 57, 1609±1614.
2. Kumar, A.; Al-Awadi, N. A.; Elnagdi, M. H.; Ibrahim, Y. A.;
Kaul, K. Int. J. Chem. Kinet. 2001, 33, 402±406.
3. Gewald, K.; Calderon, O.; Schafer, H.; Hain, U. Liebigs Ann.
Chem. 1984, 1390±1394.
1
6g, MS: m/z203 (M1); IR (KBr) 3300, 1625; H NMR
(CDCl3): d 7.00±7.7 (m, 7H), 7.9 (m, 1H), 10.10 (br s, 1H).
3.2.4. Compounds 7a±e. 7a, MS: m/z131 (M1); IR
1
(KBr): 2230, 1680; H NMR (CDCl3): d, 7.25±7.83 (m,
3H), 8.00±8.67 (m, 2H).
4. The Merck Index, 12th ed.; Windholz, M., Ed.; Merck and Co
Inc: Rahway, NJ; p 696, FT-NMR Aldrich Catalog 1(2),
451A, FT-IR 1(1), 1189A.
7b, MS: m/z145 (M1); IR (KBr): 2225, 1670.
7c, MS: m/z161 (M1); IR (KBr): 2220, 1675.
7d, MS: m/z121 (M1); IR (KBr): 2231, 1664.
5. The Merck Index, 12th ed.; Windholz, M., Ed.; Merck and Co
Inc: Rahway, NJ; p 4265, FT-NMR Aldrich Catalog 1(2),
1359A, FT-IR 1(2), 355A.
6. The Merck Index, 12th ed.; Windholz, M., Ed.; Merck and Co
Inc: Rahway, NJ; p 1088, FT-NMR Aldrich Catalog 1(2),
1402B, FT-IR 1(2), 375C.
7e, MS: m/z137 (M1); IR (KBr): 2220, 1648; H NMR
1
7. Beil. 10, 659, NMR Aldrich Catalog II(2), 403B, FT-IR 1(2),
428A.
(CDCl3): d 7.34 (m, 1H), 7.93±8.22 (m, 2H).
8. The Merck Index, 12th ed.; Windholz, M., Ed.; Merck and Co
Inc: Rahway, NJ; p 6974, FT-NMR Aldrich Catalog 1(2),
473A, FT-IR 1(1), 1202B.
3.2.5. Compounds 12±15. 12 (XCN), MS: m/z118
(M1); 13C NMR (CDCl3): d 139.8, 130.8, 123.9, 116.3,
111.6.
9. Villineuve, G. B.; Chan, T. H. Tetrahedron Lett. 1997, 38 (37),
6489±6492.
12 (XCOMe), MS: m/z135 (M1); IR (KBr): 3280, 1740;
13C NMR (CDCl3): d 169.5, 138.2, 128.7, 124.1, 120.4,
24.1.
10. Yuzuri, T.; Suezawa, H.; Hirota, M. Bull. Chem. Soc. Jpn
1994, 67, 1664±1673.
11. Beil. 13, 435, NMR Aldrich Catalog II(1), 1013B, IR III,
724E.
12 (XCOOEt), MS: m/z165 (M1); IR (KBr): 3330,
1720; 13C NMR (CDCl3): d 153.5, 137.7, 128.5, 122.9,
118.5, 60.9, 14.5.
12. Nunno, L. D.; Scilimati, A. Tetrahedron 1986, 42 (14), 3913±
3920.
13. Murahashi, S.-I.; Naota, T. Synthesis 1993, 433±440.
14. Harle, H.; Jochims, J. C. Chem. Ber. 1986, 1400±1412.
15. Toda, F.; Miyamoto, H.; Kanemoto, K.; Tanaka, K.; Takahashi,
Y.; Takenaka, Y. J. Org. Chem. 1999, 64, 2096±2102.
16. Tanaka, M. Tetrahedron Lett. 1980, 21, 2959±2962.
17. Papadopoulos, E. P. J. Org. Chem. 1974, 2540±2542.
18. Tanaka, M. Bull. Chem. Soc. Jpn 1981, 637±638.
19. Blake, A. J.; McNab, H.; Murray, M. E. A. J. Chem. Soc.
Perkin Trans. I 1989, 589±595 and referencescited therein.
20. Bradamante, S.; Pagani, G. A. J. Org. Chem. 1980, 45, 114±122.
21. Abdel-Khalik, M. M.; El-Nagdi, M. H.; Agamy, S. M.
Synthesis 2000, 8, 1166±1169.
13 (XCOMe), MS: m/z69 (M1); IR (KBr): 2220, 1730;
1H NMR (CDCl3): d 2.25 (s).
13 (XCOOEt), MS: m/z99 (M1); IR (neat): 2993, 2247,
1752; 1H NMR (CDCl3): d 1.39 (t, J7.1 Hz, 3H), 4.41 (q,
J7.1 Hz, 2H); 13C NMR (CDCl3): d 144.6, 109.8, 65.2,
14.0.
14, MS: m/z286 (M1); IR (KBr): 2241; 1H NMR (DMSO-
d6): d, 7.29±7.42 (m, 10H).
22. The Merck Index, 12th ed.; Windholz, M., Ed.; Merck and Co
Inc: Rahway, NJ; p 6098, FT-NMR Aldrich Catalog 1(2),
452A, FT-IR 1(1), 1189C.
1
15, MS: m/z149 (M1); IR (KBr): 3040, 2930, 1655; H
NMR (CDCl3): d 1.87 (s, 3H), 3.27 (s, 3H), 7.20 (m, 2H),
7.30±7.37 (m, 1H), 7.39±7.46 (m, 2H); 13C NMR (CDCl3):
d 170.5, 144.6, 129.7, 127.7, 127.1, 37.1, 22.4.
23. Compared with IR and NMR spectra measured for pure
sample purchased from Aldrich Chemical Company.
24. The Merck Index, 12th ed.; Windholz, M., Ed.; Merck and Co
Inc: Rahway, NJ; p 47, FT-NMR Aldrich Catalog 1(2), 1360B,
FT-IR 1(2), 356B.
3.2.6. N-Methylaniline. MS: m/z107 (M1); 13C NMR
(CDCl3): d 149.3, 129.1, 117.1, 112.3, 30.6.
25. Paredes, R.; Bastos, H.; Montoya, R.; Chavez, A. L.
Tetrahedron 1988, 6821±6830.
3.2.7. N,N-Dimethylaniline. MS: m/z121 (M1); 13C
NMR (CDCl3): d 150.6, 129.0, 116.6, 112.6, 40.5.
26. Baudin, J.-B.; Julia, S. A.; Ruel, O. Tetrahedron 1987, 43 (5),
881±889.
27. The Merck Index, 12th ed.; Windholz, M., Ed.; Merck and Co
Inc: Rahway, NJ; p 3284, FT-NMR Aldrich Catalog 1(2),
454C, FT-IR 1(1), 1191B.
Acknowledgements
28. Sharp, J. T.; Gosney, I.; Rowley, A. G. Practical Organic
Chemistry; Chapman & Hall: London, 1989; p 51.
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