Journal of the Iranian Chemical Society
7.09–7.32 (m, 3H, Ar–H), 7.71 (s, 1H, Ar–H), 13.13 (s,
1H, OH). 13C-NMR (CDCl3, 75 MHz, δ, ppm): 23.6,
27.1, 29.8, 45.8, 50.6, 51.3, 53.7, 104.5, 113.9, 121.7,
126.8, 129.6, 130.3, 130.8, 134.0, 134.6, 135.3, 149.8,
179.6, 196.5, 206.8. MS (m/z): 431. Elemental analysis
for C23H23Cl2NO3 (%): C, 63.90; H, 5.36; N, 3.24. Found:
C, 63.87; H, 5.29; N, 3.53.
C=CCH2), 2.06 (s, 3H, CH3COCH2), 2.35 (s, 3H,
CH3COC=C), 2.48 (d, 1H, J = 8.7 Hz, COCH2), 2.60 (d,
1H, J=8.7 Hz, COCH2), 3.86 (s, 3H, OCH3), 5.29 (s, 1H,
CHBenzyl), 6.90–6.97 (m, 4H, Ar–H), 7.53 (d, 2H, J=8.7 Hz,
Ar–H), 8.19 (d, 2H, J=8.7 Hz, Ar–H), 13.19 (s, 1H, OH).
13C-NMR (CDCl3, 75 MHz, δ, ppm): 23.7, 27.0, 29.7, 45.8,
50.9, 53.1, 55.8, 56.9, 104.4, 115.1, 115.2, 127.3, 127.9,
140.3, 144.2, 146.2, 152.7, 179.0, 196.3, 206.5. MS (m/z,
%): 421 (13), 419 (30), 375 (100), 359 (36), 327 (55), 295
(84), 238 (35), 210 (29), 148 (52), 92 (28), 77 (45), 57 (68),
43 (98), 30 (67). Elemental analysis for C24H26N2O6 (%): C,
65.74; H, 5.98; N, 6.39. Found: C, 65.62; H, 6.12; N, 6.43.
1‑(5‑Acetyl‑1,6‑bis(4‑chlorophenyl)‑4‑hydroxy‑2‑me‑
thyl‑1,2,3,6‑tetrahydropyridin‑2‑yl)propan‑2‑one (4g)
Yield = 95%. m.p. 238–240 °C. IR (KBr, cm−1): ν 3405
1
(OH), 1701 (CO). H-NMR (CDCl3, 300 MHz, δ, ppm):
1.22 (s, 3H, CH3), 1.63 (d, 1H, J = 8.1 Hz), 1.75 (s, 3H,
CH3COCH2), 1.80 (s, 3H, CH3COC=C), 2.52 (ABq, 2H,
C=CCH2), 2.81(d, 1H, J=8.1 Hz), 3.42 (s, 1H, CHBenzyl),
7.08 (d, 2H, J = 8.4 Hz, Ar–H), 7.14 (d, 2H, J = 8.4 Hz,
Ar–H), 7.30–7.37 (m, 4H, Ar–H), 13.01 (s, 1H, OH). 13C-
NMR (CDCl3, 75 MHz, δ, ppm): 28.1, 29.7, 34.9, 40.6, 45.0,
63.4, 68.7, 105.7, 127.1, 129.0, 129.3, 131.2, 132.5, 137.2,
144.2, 154.8, 179.8, 198.4, 215.9. MS (m/z): 431. Elemental
analysis for C23H23Cl2NO3 (%): C, 63.90; H, 5.36; N, 3.24.
Found: C, 63.90; H, 5.32; N, 3.62.
1‑(5‑Acetyl‑4‑hydroxy‑1‑(4‑methoxyphenyl)‑2‑me‑
thyl‑6‑(4‑phenylcyanide)‑1,2,3,6‑tetrahydropyridin‑2‑yl)
propan‑2‑one (4j) Yield=78%. m.p. 88–90 °C. IR (KBr,
cm−1): ν 3397 (OH), 2254 (CN), 1596 (C=C), 1249 (COC).
1H-NMR (CDCl3, 300 MHz, δ, ppm): 1.66 (s, 3H, CH3),
1.90 (d, 1H, J=6.9 Hz, C=CCH2), 2.08 (s, 3H, CH3C-
OCH2), 2.21 (s, 3H, CH3COC=C), 2.32 (d, 1H, J=6.9 Hz,
C=CCH2), 2.50 (d, 1H, J=8.4 Hz, COCH2), 2.57 (d, 1H,
J=8.1 Hz, COCH2), 3.80 (s, 3H, OCH3), 4.60 (s, 1H,
CHBenzyl), 6.85 (d, 2H, J=8.4 Hz, Ar–H), 7.16 (d, 2H,
J=8.4 Hz, Ar–H), 7.31 (d, 2H, J=8.4 Hz, Ar–H), 7.49
(d, 2H, J=8.4 Hz, Ar–H), 12.80 (s, 1H, OH). 13C-NMR
(CDCl3, 75 MHz, δ, ppm): 23.8, 27.4, 30.1, 45.9, 50.6, 53.5,
55.5, 55.8, 104.2, 111.5, 114.8, 115.0, 118.1, 128.3, 132.4,
141.7, 142.1, 152.8, 178.6, 196.6, 206.1. MS (m/z): 418.
Elemental analysis for C25H26N2O4 (%): C, 71.75; H, 6.26;
N, 6.69. Found: C, 71.92; H, 6.04; N, 6.54.
1‑(5‑Acetyl‑1‑(4‑chlorophenyl)‑4‑hydroxy‑2‑me‑
thyl‑6‑(4‑nitrophenyl)‑1,2,3,6‑tetrahydropyridin‑2‑yl)
propan‑2‑one (4h)
Yield = 82%. m.p. 84–85 °C. IR (KBr, cm−1): ν 3428
1
(OH), 1592 (NO2), 1383 (NO2), 1109 (CN). H-NMR
(CDCl3, 300 MHz, δ, ppm): 1.38 (s, 3H, CH3), 1.76 (ABq,
2H, C=CCH2), 1.99 (s, 3H, CH3COCH2), 2.20 (s, 3H,
CH3COC=C), 2.64 (d, 1H, J = 7.5 Hz, COCH2), 2.88 (d,
1H, J = 7.8 Hz, COCH2), 4.44 (s, 1H, CHBenzyl), 6.61 (d,
2H, J=7.8 Hz, Ar–H), 7.05 (d, 2H, J=8.4 Hz, Ar–H), 7.52
(d, 2H, J=8.4 Hz, Ar–H), 8.16 (d, 2H, J=8.7 Hz, Ar–H),
12.91 (s, 1H, OH). 13C-NMR (CDCl3, 75 MHz, δ, ppm):
24.3, 27.3, 31.0, 45.5, 50.8, 53.4, 56.4, 104.9, 115.5, 125.8,
127.2, 128.3, 128.9, 143.2, 146.2, 147.8, 179.8, 197.1,
206.2. MS (m/z, %): 440 (5), 425 (12), 396 (8), 379 (12),
344 (23), 263 (13), 250 (4), 192 (16), 179 (8), 122 (10), 98
(17), 77 (33), 63 (10), 43 (100), 29 (9). Elemental analysis
for C23H23ClN2O5 (%): C, 62.37; H, 5.23; N, 6.33. Found:
C, 62.21; H, 5.44; N, 6.39.
References
1. Z. Ma, F. Zaera, in Encyclopedia of Inorganic and Bioinorganic
Chemistry. ed. by R.A. Scott (Wiley, London, 2011)
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1‑(5‑Acetyl‑4‑hydroxy‑1‑(4‑methoxyphenyl)‑2‑me‑
thyl‑6‑(4‑nitrophenyl)‑1,2,3,6‑tetrahydropyridin‑2‑yl)
propan‑2‑one (4i)
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Yield = 79%. m.p. 213–215 °C. IR (KBr, cm−1): ν 3397
(OH), 1612 (CO), 1511 (NO2), 1345 (NO2), 1249 (COC).
1H-NMR (CDCl3, 300 MHz, δ, ppm): 1.58 (s, 3H, CH3),
1.80 (d, 1H, J=8.4 Hz, C=CCH2), 1.84 (d, 1H, J=8.4 Hz,
11. T. Ohno, T. Mitsui, M. Matsumura, Chem. Lett. 32, 364 (2003)
12. T. Ohno, M. Akiyoshi, T. Umebayashi, K. Asai, T. Mitsui, M.
Matsumura, Appl. Catal. A 265, 115 (2004)
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