654
L. L. SEIAD ET AL.
Recycling
The diethyl ether filtrate was evaporated, and the resulting liquid was used
instead of DBU for performing the same reaction. Six runs were performed with 2a.
Selected Data
(E)-2-(4-Methoxystyryl)-1-methylpyridinium iodide (1a). Yield 60%, mp
235 ꢀC,[14] IR (cmꢁ1): 1680. 1H NMR (ppm): 3.84 (s, 3H, OCH3), 4.34 (s, 3H,
þ
=
N CH3), 7.06 (d, 8.8 Hz, 2H, Ar), 7.44 (d, 16.2 Hz, 1H, CH CH), 7.83 (d, 8.8 Hz,
=
2H, Ar), 7.84 (m, 1H, Ar), 7.92 (d, 16.2 Hz, 1H, CH CH), 8.44 (m, 1H, Ar), 8.47
(m, 1H, Ar), 8.84 (d, 6.4 Hz, 1H, Ar). 13C NMR (ppm): 46.01, 55.50, 114.54 (2C),
114.75, 124.43, 124.46, 127.57, 130.54 (2C), 142.85, 143.93, 145.79, 152.71, 161.44.
EIMS m=z (% relative abundance): 226 (Mþ, 62), 211 (100), 182 (30). HRMS
(ESI-TOF): calcd for C15H16NO 226.1232, found 226.1229.
(E)-1-Ethyl-4-(4-methoxystyryl)pyridinium iodide (1b). Yield 30%, mp
214 ꢀC,[15] IR (cmꢁ1): 1677.1H NMR (ppm): E stereoisomer 1.46 (t, 10.5 Hz, 3H,
CH3), 3.87 (s, 3H, OCH3), 4.50 (m, 2H, NþCH2), 7.14 (m, 2H, Ar), 7.35 (d,
=
=
16.4 Hz, 1H, CH CH), 7.71 (d, 8.8 Hz, 2H, Ar), 8.00 (d, 16.4 Hz, 1H, CH CH),
8.17 (d, 6.8 Hz, 2H, Ar), 8.90 (m, 2H, Ar). Z stereoisomer 1.52 (t, 10.5 Hz, 3H,
CH3), 3.87 (s, 3H, OCH3) 4.50 (m, 2H, NþCH2), 6.75 (d, 8.8 Hz, 2H, Ar), 7.08
(m, 2H, Ar), 7.88 (m, 3H, Ar and CH CH), 8.92 (m, 3H, CH CH and Ar). 13C
NMR (ppm): 16.18, 39.73, 54.7, 111.08, 112.02 (2C), 117.07, 122.55 (2C), 130.26
(2C), 142.08, 143.28 (2C), 151.93, 153.73. EIMS m=z (% relative abundance): 240
(Mþ, 100), 225 (92). HRMS (ESI-TOF): calcd for C16H18NO 240.1388; found
240.1394.
=
=
(E)-2-(4-Methoxystyryl)-1-methylquinolinium iodide (1c). Yield 60%, mp
1
236–237 ꢀC,[16] IR (cmꢁ1): 1678. H NMR (ppm): 3.88 (s, 3H, OCH3), 4.56 (s, 3H,
þ
=
N CH3), 7.12 (d, 8.8 Hz, 2H, Ar), 7.81 (d, 15.2 Hz, 1H, CH CH), 7.95 (t, 8.0 Hz,
1H, Ar), 7.99 (d, 8.8 Hz, 2H, Ar), 8.18 (t, 8.0 Hz, 1H, Ar), 8.25 (d, 15.2 Hz, 1H,
=
CH CH), 8.35 (d, 8.0 Hz, 1H, Ar), 8.55 (d, 8.8 Hz, 1H, Ar), 8.57 (d, 9.2 Hz, 1H,
Ar), 9.03 (d, 9.2 Hz, 1H, Ar). 13C NMR (ppm): 39.7, 55.6, 114.77 (2C), 116.60,
119.29, 120.88, 127.69, 127.69, 128.80, 129.99, 131.42 (2C), 134.75, 139.18, 143.63,
147.19, 156.47, 162.25. EIMS m=z (% relative abundance): 276 (Mþ, 85), 161
(100), 168 (54), 232 (52). HRMS (ESI-TOF): calcd for C19H18NO 276.1388; found
276.1400.
(E)-2-(4-(Dimethylamino)styryl)-1-methylpyridinium iodide (2a). Yield
1
90%, mp 273–2þ74 ꢀC,[17] IR (cmꢁ1): 1630. H NMR (ppm): 3.02 [s, 6H, N(CH3)2],
=
4.30 (s, 3H, N CH3), 6.79 (d, 8.0 Hz, 2H, Ar), 7.24 (d, 15.2 Hz, 1H, CH CH),
=
7.71 (m, 1H, Ar), 7.72 (d, 8.0 Hz, 2H, Ar), 7.93 (d, 15.2 Hz, 1H, CH CH), 8.35 (t,
8.4 Hz, 1H, Ar), 8.46 (d, 8.4 Hz, 1H, Ar), 8.77 (d, 6.0 Hz, 1H, Ar). 13C NMR
(ppm): 39.58 (2C), 45.70, 110.61, 111.78 (2C), 122.34, 123.04, 123.60, 130.75,
143.09 (2C), 144.21, 145.29, 152.11, 153.28. EIMS m=z (% relative abundance):
239 (Mþ, 65), 223 (100), 134 (32). HRMS (ESI-TOF): calcd for C16H19N2
239.1548; found 239.1540.