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196–198◦C. IR (KBr): 3426 cm−1 (OH) and 2217 cm−1 (C N); 1H NMR
spectrum (300 MHz; DMSO-d6) δ 3.81 (q, 2H, J = 5.29 Hz, CH2OH(d)),
4.54 (t, 2H, J = 5.01 Hz, OCH2(c)), 4.93 (t, 1H, J = 5.29 Hz, OH), 6.01
(s, 2H, OCH2O(a)), 7.23 (t, 1H, J = 3.99, 4.56 Hz, thiophene-H), 7.65
(d, 2H, J = 8.45 Hz, Ar-H), 7.73 (d, 2H, J = 8.45 Hz, Ar-H), 7.77 (s, 1H,
pyridine-H-5), 7.85 (d, 1H, J = 4.56 Hz, thiophene-H), 8.07 (d, J = 3.99 Hz,
1H, thiophene-H); 13C NMR (75 MHz DMSO-d6) δ 59.46, 69.4, (2CH2),
69.8 (OCH2O), 112.4, 115.6 (C N), 129.2, 129.3, 129.5, 130.6, 130.9,
131.8, 135.0, 135.5, 142.9, 153.3, 155.5 and 164.4 (Ar-C). Anal. Calcd. for
C19H15ClN2O3S (386.85): C, 58.99; H, 3.91; N, 7.24. Found: C, 59.01; H,
3.92; N, 7.26.
2-(3-Chloro-2-hydroxypropoxy)-4-(4-chlorophenyl)-6-(thien-2-yl)nicotino
nitrile (9). 48% yield; Pale yellow crystals; m.p. 99–100◦C; IR (KBr) 3424
cm−1 (OH) and 2217 cm−1 (C N). 1H NMR spectrum (300 MHz; DMSO-d6)
δ 3.61 (dd, 1H, J = 5.43 Hz, J = 11.13 Hz, H-a’), 3.67 (dd, 1H, J = 5.64 Hz,
J = 11.17 Hz, H-a), 3.96 (dd, 1H, J = 5.81 Hz, J = 10.23 Hz, H-c’), 4.05
(dd, 1H, J = 5.15 Hz, J = 10.23 Hz, H-c), 4.40 (m, 1H, H-b), 5.53 (d, 1H, J
= 5.23 Hz, OH), 7.11 (t, 1H, J = 4.14, 5.62 Hz, thiophene-H), 7.46 (d, 2H,
J = 8.50 Hz, Ar-H), 7.52 (d, 2H, J = 8.50 Hz, Ar-H), 7.61 (s, 1H, pyridine-
H-5), 7.70 (d, 1H, J = 5.62 Hz, thiophene-H), 7.96 (d, 1H, J = 4.14 Hz,
thiophene-H); 13C NMR (75 MHz DMSO-d6) δ 47.01 (CH2Cl), 68.4
(CHOH), 68.64 (OCH2), 92.1, 112.7, 115.4 (C N), 129.3, 129.5, 130.9,
131.9, 134.9, 135.5, 136.0, 142.8, 153.3, 155.5 and 164.1 (Ar-C). Anal. Calcd
for C19H14Cl2N2O2S (405.30): C, 56.31; H, 3.48; N, 6.91. Found: C, 56.30;
H, 3.46; N, 6.90.
4-(4-Chlorophenyl)-2-(oxiran-2-ylmethoxy)-6-(thien-2-yl)nicotinonitrile
(11). 71% yield; Pale yellow crystals; m.p. 185–187◦C; IR (KBr) 2216 cm−1
1
(C N); H NMR spectrum (300 MHz; DMSO-d6) δ 2.83 (t, 1H, J = 1.50,
4.50 Hz, H-a), 2.89 (t, 1H, J = 4.20, 4.50 Hz, H-a’), 4.29 (dd, 1H, J = 6.30
Hz, H-b), 4.83 (d, 1H, J = 2.17 Hz, H-c’), 4.88 (d, 1H, J = 2.27 Hz, H-c),
7.24 (t, 1H, J = 3.95, 4.07 Hz, thiophene-H), 7.66 (d, 2H, J = 8.43 Hz,
Ar-H), 7.74 (d, 2H, J = 8.43 Hz, Ar-H), 7.79 (s, 1H, pyridine-H-5), 7.82 (d,
1H, J = 4.07 Hz, thiophene-H), 8.10 (d, 1H, J = 3.95 Hz, thiophene-H); 13
C
NMR (75 MHz DMSO-d6) δ 44.6 (CH2O, oxiran), 49.5 (CHO, oxiran), 68.5
(OCH2), 91.8, 113.1, 115.5 (C N), 129.2, 129.4, 129.7, 130.8, 131.9, 134.4,
135.4, 142.7, 153.2, 157.7 and 163.8 (Ar-C). Anal. Calcd for C19H13ClN2O2S
(368.84): C, 61.87; H, 3.55; N, 7.60. Found: C, 61.85; H, 3.54; N, 7.61.
2-(Allyloxy)-4-(4-chlorophenyl)-6-(thien-2-yl)nicotinonitrile (13). 82%
yield; Pale yellow crystals; m.p. 201–203◦C; IR (KBr) 2216.7 cm−1 (C N); 1H
NMR spectrum (300 MHz; DMSO-d6) δ 5.08 (d, 2 H, J = 5.10 Hz, OCH2),
5.33 (d, 1H, J = 10.2 Hz, H-a), 5.52 (d, 1H, J = 17.4 Hz, H-b), 6.16 (m, 1 H,
H-c), 7.24 (t, 1H, J = 4.03, 4.56 Hz, thiophene-H), 7.67 (d, 2H, J = 8.40 Hz,
Ar-H), 7.76 (d, 2H, J = 8.40 Hz, Ar-H), 7.80 (s, 1H, pyridine-H-5), 7.83 (d,
1H, J = 4.56 Hz, thiophene-H), 8.11 (d, 1H, J = 4.03 Hz, thiophene-H);