368
Product 4e: 1H-NMR (CDCl3, 200 MHz) d: 7.29—7.02 (9H, m), 6.02
(1H, d, Jꢀ7.5 Hz), 4.88 (1H, dd, Jꢀ7.5, 5.5 Hz), 4.62 (1H, d, Jꢀ5.5 Hz),
3.99 (2H, q, Jꢀ7.0 Hz), 2.04 (3H, s), 1.03 (3H, t, Jꢀ7.0 Hz); FAB-MS m/z:
337 (Mꢁ); Anal. Calcd for C21H20FNO2: C, 74.78; H, 5.93; N, 4.15%.
Found: C, 74.87; H, 5.84; N, 4.08%.
Vol. 56, No. 3
d, Jꢀ7.5 Hz), 4.91 (1H, dd, Jꢀ7.5, 5.5 Hz), 4.65 (1H, d, Jꢀ5.5 Hz), 3.58
(3H, s), 2.06 (3H, s); FAB-MS m/z: 323 (Mꢁ); Anal. Calcd for C20H18FNO2:
C, 74.30; H, 5.57; N, 4.33%. Found: C, 74.51; H, 5.48; N, 4.41%.
Acknowledgements The authors thank CSIR and UGC, New Delhi for
Product 4f: 1H-NMR (CDCl3, 200 MHz) d: 7.56 (2H, d, Jꢀ8.0 Hz),
7.40—7.26 (5H, m), 7.14 (2H, d, Jꢀ8.0 Hz), 6.18 (1H, d, Jꢀ7.5 Hz), 4.98
(1H, dd, Jꢀ7.5, 5.5 Hz), 4.75 (1H, d, Jꢀ5.5 Hz), 4.04 (2H, q, Jꢀ7.0 Hz),
2.18 (3H, s), 1.10 (3H, t, Jꢀ7.0 Hz); FAB-MS m/z: 399, 397 (Mꢁ); Anal.
Calcd for C21H20BrNO2: C, 63.32; H, 5.03; N, 3.52%. Found: C, 63.51; H,
5.17; N, 3.44%.
financial assistance.
References and Notes
1) Part 152, “Studies on Novel Synthetic Methodologies.”
2) Prokai L., Prokai-Tatrai K., Bodor N., Med. Res. Rev., 20, 367—416
(2000).
3) Misral A., Ganesh S., Shahiwala A., Shah S. P., J. Pharm. Pharma-
ceut. Sci., 6, 252—273 (2003).
4) Cai X., Yang H., Zhang G., Can. J. Chem., 83, 273—275 (2005).
5) Zampani G. W., Stotz S. C., Staples R. J., Andro T. M., Nelson J. K.,
Hulubei V., Blumenfeld A., Natale N. R., J. Med. Chem., 46, 87—96
(2003).
6) Visentine S., Rolando B., Stilo A. D., Fruttero R., Novaro M., Carbone
E., Roussel C., Vanthuyme N., Gasco A., J. Med. Chem., 47, 2688—
2693 (2004).
7) Litvic M., Cepanec I., Filipan M., Kos K., Bartolincic A., Druskovic
V. , Tibi M. M., Vinkovic V., Heterocycles, 65, 23—35 (2005).
8) Kumar R., Chandra R., Adv. Heterocycl. Chem., 78, 269—313 (2001).
9) Lavilla R., J. Chem. Soc., Perkin Trans I, 2002, 1141—1156 (2002).
10) For a review: Simon C., Constantieux T., Rodriguez J., Eur. J. Org.
Chem., 2004, 4957—4980 (2004).
11) Das B., Chowdhury N., J. Mol. Catal. A: Chem., 263, 212—215
(2007).
12) Das B., Chowdhury N., Damodar K., Reddy K. R., Helv. Chim. Acta,
90, 340—345 (2007).
Product 4g: 1H-NMR (CDCl3, 200 MHz) d: 7.40—7.21 (9H, m), 6.15
(1H, d, Jꢀ7.5 Hz), 5.01 (1H, dd, Jꢀ7.5, 5.5 Hz), 4.75 (1H, d, Jꢀ5.5 Hz),
4.01 (2H, q, Jꢀ7.0 Hz), 2.16 (3H, s), 1.08 (3H, t, Jꢀ7.0 Hz); FAB-MS m/z:
355, 353 (Mꢁ); Anal. Calcd for C21H20ClNO2: C, 71.29; H, 5.66; N, 3.96%.
Found: C, 71.38; H, 5.73; N, 3.91%.
Product 4h: 1H-NMR (CDCl3, 200 MHz) d: 7.38—7.12 (8H, m), 6.17
(1H, d, Jꢀ7.5 Hz), 5.02 (1H, dd, Jꢀ7.5, 5.5 Hz), 4.73 (1H, d, Jꢀ5.5 Hz),
3.99 (2H, q, Jꢀ7.0 Hz), 2.29 (6H, s), 2.17 (3H, s), 1.10 (3H, t, Jꢀ7.0 Hz);
FAB-MS m/z: 347 (Mꢁ); Anal. Calcd for C23H25NO2: C, 79.54; H, 7.21; N,
4.04%. Found: C, 79.68; H, 7.29; N, 4.18%.
Product 4i: 1H-NMR (CDCl3, 200 MHz) d: 7.33—6.95 (9H, m), 6.11 (1H,
d, Jꢀ7.5 Hz), 4.93 (1H, dd, Jꢀ7.5, 5.5 Hz), 4.62 (1H, d, Jꢀ5.5 Hz), 3.53
(3H, s), 2.39 (3H, s), 2.11 (3H, s); FAB-MS m/z: 319 (Mꢁ); Anal. Calcd for
C21H21NO2: C, 79.00; H, 6.58; N, 4.34%. Found: C, 79.18; H, 6.46; N,
4.45%.
Product 4j: 1H-NMR (CDCl3, 200 MHz) d: 7.57—7.05 (9H, m), 6.12
(1H, d, Jꢀ7.5 Hz), 4.96 (1H, dd, Jꢀ7.5, 5.5 Hz), 4.62 (1H, d, Jꢀ5.5 Hz),
3.81 (3H, s), 3.53 (3H, s), 2.03 (3H, s); FAB-MS m/z: 335 (Mꢁ); Anal. Calcd
for C21H21NO3: C, 75.22; H, 6.27; N, 4.18%. Found: C, 75.11; H, 6.35; N,
4.27%.
13) Sridharan V., Perumal P. T., Avendano C., Menendez J. C.,
Tetrahedron, 63, 4407—4413 (2007).
14) Shylesh A., Sharma S., Mirjkar S. P., Singh A. P., J. Mol. Catal. A:
Chem., 212, 219—228 (2004).
15) Karimmi B., Khalkhali M. J., J. Mol. Catal. A: Chem., 232, 113—117
(2005).
Product 4k: 1H-NMR (CDCl3, 200 MHz) d: 7.51—7.32 (7H, m), 7.08
(2H, d, Jꢀ8.0 Hz), 6.14 (1H, d, Jꢀ7.5 Hz), 4.95 (1H, dd, Jꢀ7.5, 5.5 Hz),
4.64 (1H, d, Jꢀ5.5 Hz), 3.54 (3H, s), 2.37 (3H, s), 2.10 (3H, s); FAB-MS
m/z: 319 (Mꢁ); Anal. Calcd for C21H21NO2: C, 79.00; H, 6.58; N, 4.39%.
Found: C, 79.26; H, 6.69; N, 4.28%.
Product 4l: 1H-NMR (CDCl3, 200 MHz) d: 7.38—7.15 (9H, m), 6.08 (1H,