Table 2.
Characterization of Dihydropyridine and Pyridine Derivatives
| no. | Tm (°C) | formula | MS | analysis | yielda (%) | |
|---|---|---|---|---|---|---|
|
| ||||||
| 9 | 148–149 | C21H25NO4 | 355(CI) | C,H,N | 16.3 | |
| 10 | 115–117 | C26H27NO4 | 417 (CI) | C,H,N | 69.5 | |
| 12 | 106–108 | C20H25NO4 | 343 (CI) | C,H,N | 25.5 | |
| 13 | 112–114 | C24H25NO4 | 391 (EI) | C,H,N | 62.9 | |
| 14 | 129–131 | C27H29NO4 | 431 (CI) | C,H,N | 32.2 | |
| 15 | 137–139 | C21H33NO4 | 447 (CI) | C,H,N | 6.1 | |
| 16 | 149–151 | C26H26NClO4 | 451 (EI) | C,H,N | 31.2 | |
| 17 | oil | C26H26N2O6 | 462 (EI) | b | 15.3 | |
| 18 | 114–116 | C24H25NO5 | 407 (CI) | C,H,N | 25.5 | |
| 19 | oil | C24H25NSO4·0.50EtOH | 423 (EI) | C,H,N | 15.1 | |
| 20 | 130–132 | C27H29NO5 | 447 (EI) | C,H,N | 12.0 | |
| 21 | 175–176 | C26H26N2O6 | 462 (EI) | C,H,N | 8.0 | |
| 22 | 195–196 | C26H26N2O6 | 462 (EI) | C,H,N | 58.2 | |
| 23 | oil | C26H28N2O4 | 432 (EI) | c | 24.1 | |
| 24 | 164–165 | C32H31NO4 | 491 (EI) | C,H,N | 8.2 | |
| 25 | 132–134 | C26H25NO4 | 415 (EI) | C,H,N | 36.4 | |
| 26 | 161–163 | C31H29NO4 | 479 (EI) | C,H,N | 27.9 | |
| 27 | oil | C31H28N2O6 | 524 (EI) | d | 26.2 | |
| 28 | 156–158 | C31H27NO4 | 477 (CI) | C,H,N | 31.0 | |
| 29 | 149–151 | C31H29NO4 | 479 (EI) | C,H,N | 41.5 | |
| 30 | oil | C31H28N2O6 | 524 (EI) | e | 32.9 | |
| 31 | 124–125 | C31H27NO4 | 477 (CI) | C,H,N | 29.3 | |
| 33 | oil | C26H25NO4 | 415 (EI) | f | 29.8 | |
| 34 | oil | C31H25NO4 | 475 (EI) | g | 74.0 | |
Purification was achieved by thin layer chromatography, silica 60, 1000 μm layer thickness, using EtOAc-petroleum ether (pe) 35–60, 20:80 (v/v) as eluent.
17 pure on analytical TLC (silica 60, 250 μm) EtOAc-pe = 20:80 (v/v), Rf = 0.21; CH2Cl2-MeOH = 40:1 (v/v), Rf = 0.46; EI calcd 462.1806, found 462.1791.
23 (C26H28N2O4) insufficient quantity for CHN, pure on analytical TLC (silica 60, 250 μm) EtOAc-pe = 20:80 (v/v), Rf = 0.06; CHCl3-MeOH-CH3COOH = 94:6:1 (v/v/v), Rf = 0.47; EI calcd 432.2049, found 432.2042.
27 pure on analytical TLC (silica 60, 250 μm) EtOAc-pe = 20:80 (v/v), Rf = 0.23; CH2Cl2-MeOH = 40:1 (v/v), Rf = 0.68; EI calcd 524.1938, found 524.1947.
30 pure on analytical TLC (silica 60, 250 μm) EtOAc-pe = 20:80 (v/v), Rf = 0.21; CH2Cl2-MeOH = 40:1 (v/v), Rf = 0.71; EI calcd 524.1938, found 524.1928.
33 pure on analytical TLC (silica 60, 250 μm) EtOAc-pe = 20:80 (v/v), Rf = 0.62; CH2Cl2-MeOH = 40:1 (v/v), Rf = 0.69; EI calcd 415.1772, found 415.1783.
34 pure on analytical TLC (silica 60, 250 μm) EtOAc-pe = 20:80 (v/v), Rf = 0.52; CH2Cl2-MeOH = 40:1 (v/v), Rf = 0.75; EI calcd 475.1776, found 475.1783.