Y.S. Kara / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 151 (2015) 723–730
725
solution of cis-1,4-diacetoxy-2-butene (0.52 g, 3 mmol) in
dichloromethane (15 mL) at ꢁ10 °C, and solution of
N-hydroxy-benzenecarboximidoyl chloride in dichloromethane
15 mL) was added dropwise under stirred. The reaction mixture
was stirred for 24 h at room temperature. The reaction mixture fil-
tered through filter paper, and the solution was evaporated at
reduced pressure. The residue was subjected to dry-flash chro-
matography on silica gel using hexane–ethyl acetate (4:1) as elu-
ent. The product was crystallized in (ethyl acetate/petroleum
2.14 (s, 3H, CH
3
)(C21), 2.05 (s, 3H, CH
3
)(C20); 13C NMR (CDCl
3
), d
a
(ppm): 170.57 (C@O18), 170.44 (C@O14), 156.94 (C@N), 132.29–
124.99 (aromatic C), 81.33 (CH)(C5), 61.37 (CH )(C12), 59.19
(CH )(C16), 47.86 (CH)(C4), 20.80 (CH )(C21), 20.72 (CH )(C20);
Anal. Calcd for C15 16 BrNO (370.195): C, 48.67; H, 4.36; N,
2
(
2
3
3
H
5
3.78, Found C, 48.52; H, 4.31; N, 3.88.
3.1.5. (3-(4-Chlorophenyl)-4,5-dihydroisoxazole-4,5-diyl)-
bis(methylene) diacetate(3e)
ether, 1:3) to give (3a) 250 mg (35%); mp 103–104 °C; IR (KBr),
m
270 mg (31%); mp 94–95 °C; IR (KBr),
m
(cmꢁ1): 1733.89 (C@O),
), d (ppm): 7.70–7.68 (d, J = 8.8, aro-
matic, 2H), 7.42–7.40 (d, J = 8.8, aromatic, 2H), 4.87–4.82 (td,
ꢁ1
1
1
(
cm ): 1747.39 (C@O), 1731.96 (C@O), 1600.81 (C@N); H NMR
1595.02 (C@N); H NMR (CDCl
3
(
CDCl ), d (ppm): 7.75–7.73 (m, aromatic, 2H), 7.44–7.43 (m, aro-
3
matic, 3H), 4.87–4.82 (td, J = 3.2, J = 4, H, CH) (C5), 4.67–4.63 (dd,
J = 8, J = 3.7, H, CH ) (C12), 4.48–4.43 (dd, J = 4.8, J = 7.6, H, CH
C16), 4.38–4.34 (dd, J = 8.4, J = 3.2, H, CH ) (C12), 4.18–4.13 (dd,
J = 3.2, J = 8.8, H, CH ) (C16), 4.03–3.98 (td, J = 4.8, J = 3.6, H, CH)
J = 3.2, J = 4.4, H, CH) (C5), 4.66–4.63 (dd, J = 8, J = 4, H, CH
(C12), 4.48–4.43 (dd, J = 4.8, J = 7.2, H, CH
J = 8.4, J = 3.6, H, CH ) (C12), 4.17–4.12 (dd, J = 4, J = 8.4, H, CH
2
2
)
2
2
)
2
) (C16), 4.35–4.31 (dd,
(
2
2
)
2
(C16), 3.98–3.93 (td, J = 5.2, J = 3.2, H, CH) (C4), 2.13 (s, 3H,
1
3
13
(
C4), 2.13 (s, 3H, CH
CDCl ), d (ppm): 170.61 (C@O18), 170.46 (C@O14), 157.71 (C@N),
30.58–127.02 (aromatic C), 81.05 (CH)(C5), 61.54 (CH )(C12),
9.37 (CH )(C16), 48.03 (CH)(C4), 20.81 (CH )(C21), 20.71
)(C20), 77.059 (CDCl ); Anal. Calcd for C15 (291.299):
C, 61.85; H, 5.88; N, 4.81, Found C, 61.61; H, 5.84; N, 4.79.
3
)(C21), 2.03 (s, 3H, CH
3
)(C20); C NMR
CH
170.58 (C@O18), 170.47 (C@O14), 156.85 (C@N), 136.65–126.66
(aromatic C), 81.30 (CH)(C5), 61.38 (CH )(C12), 59.19 (CH )(C16),
47.92 (CH)(C4), 20.80 (CH )(C21), 20.72 (CH )(C20); Anal. Calcd
for C15 16 ClNO (325.744): C, 55.31; H, 4.95; N, 4.30, Found C,
3 3 3
)(C21), 2.04 (s, 3H, CH )(C20); C NMR (CDCl ), d (ppm):
(
3
1
5
2
2
2
2
3
3
3
(
CH
3
3
H17NO
5
H
5
55.33; H, 4.93; N, 4.41.
3
.1.2. (3-p-Tolyl-4,5-dihydroisoxazole-4,5-diyl)bis(methylene)
diacetate(3b)
40 mg (33%); mp 102–103.5 °C; IR (KBr),
3.1.6. (3-(4-(Trifluoromethyl)phenyl)-4,5-dihydroisoxazole-4,5-
diyl)bis(methylene) diacetate(3f)
225 mg (30%); mp 135–138 °C; IR (KBr),
3
(C@O), 1737.75 (C@O), 1618.17 (C@N); H NMR (CDCl ), d (ppm):
ꢁ
ꢁ1
2
m
(cm 1): 1741.60
C@O), 1733.87 (C@O), 1598.88 (C@N); H NMR (CDCl ), d (ppm):
.64–7.62 (d, J = 8.4, aromatic, 2H), 7.25–7.23 (d, J = 8, aromatic,
H), 4.85–4.80 (td, J = 4, J = 3.2, H, CH) (C5), 4.67–4.63 (dd, J = 8,
) (C12), 4.47–4.43 (dd, J = 4.8, J = 7.2, H, CH ) (C16),
.37–4.33 (dd, J = 8.4, J = 3.6, H, CH ) (C12), 4.18–4.13 (dd, J = 3.2,
J = 8.4, H, CH ) (C16), 4.00–3.96 (td, J = 5.2, J = 3.6, H, CH) (C4),
.38 (s, 3H, CH ), 2.13 (s, 3H, CH )(C21), 2.04 (s, 3H, CH )(C20);
C NMR (CDCl ), d (ppm): 170.62 (C@O18), 170.47 (C@O14),
57.64 (C@N), 140.93–125.26 (aromatic C), 80.88 (CH)(C5), 61.58
m
(cm ):1749.32
1
1
(
7
2
3
7.89–7.87 (d, J = 8, aromatic, 2H), 7.71–7.69 (d, J = 8.4, aromatic,
2H), 4.92–4.87 (td, J = 2.8, J = 4.4, H, CH) (C5), 4.68–4.64 (dd,
J = 4, H, CH
4
2
2
J = 7.6, J = 4.4, H, CH
2
) (C12), 4.50–4.45 (dd, J = 5.2, J = 7.2, H, CH
) (C12), 4.19–4.14 (dd,
) (C16), 4.04–3.99 (td, J = 5.6, J = 3.6, H, CH) (C4),
2
)
2
(C16), 4.37–4.33 (dd, J = 8.4, J = 3.6, H, CH
2
2
J = 4, J = 8, H, CH
2.14 (s, 3H, CH
2
1
3
2
3
3
3
3
3 3
)(C21), 2.04 (s, 3H, CH )(C20); C NMR (CDCl ), d
1
3
3
(ppm): 170.55 (C@O18), 170.43 (C@O14), 156.73 (C@N), 131.64–
125.97 (aromatic C), 81.61 (CH)(C5), 61.29 (CH )(C12), 59.09
(CH )(C16), 47.77 (CH)(C4), 20.77 (CH )(C21), 20.68 (CH )(C20);
Anal. Calcd for C16 NO (359.297): C, 53.49; H, 4.49; N, 3.90,
Found C, 53.45; H, 4.44; N, 4.00.
1
2
(
(
(
CH
CH
2
)(C12), 59.41 (CH
)(C21), 20.73 (CH
2
)(C16), 48.13 (CH)(C4), 21.45 (CH
(C20); Anal. Calcd for
3
), 20.81
2
3
3
3
3
)
C
16
H
19NO
5
H
16
F
3
5
305.326): C, 62.94; H, 6.27; N, 4.59, Found C, 62.62; H, 6.22; N,
4
.54.
3.1.7. (3-(4-Cyanophenyl)-4,5-dihydroisoxazole-4,5-diyl)-
3
.1.3. (3-(4-Ethylphenyl)-4,5-dihydroisoxazole-4,5-
bis(methylene) diacetate(3g)
270 mg (33%); mp 118–119.5 °C; IR (KBr),
(C„N), 1741.60 (C@O), 1587.30 (C@N); H NMR (CDCl
(ppm): 7.89–7.87 (d, J = 8.4, aromatic, 2H), 7.74–7.72 (d, J = 8.8,
aromatic, 2H), 4.93–4.87 (td, J = 2.8, J = 4.4, H, CH) (C5), 4.69–4.64
(cm 1): 2223.77
ꢁ
diyl)bis(methylene) diacetate(3c)
96 mg (31%); mp 97–98 °C; IR (KBr),
1
7
4
m
2
m
(cm 1): 1747.39 (C@O),
ꢁ
1
3
), d
1
731.96 (C@O), 1612.38 (C@N); H NMR (CDCl ), d (ppm): 7.67–
3
.65 (d, J = 8.4, aromatic, 2H), 7.27–7.25 (d, J = 8.4, aromatic, 2H),
.85–4.79 (td, J = 3.2, J = 4 H, CH) (C5), 4.67–4.63 (dd, J = 8, J = 4,
(dd, J = 8, J = 4, H, CH
CH ) (C16), 4.35–4.31 (dd, J = 8.4, J = 3.6, H, CH
(dd, J = 4, J = 8.4, H, CH ) (C16), 4.02–3.97 (td, J = 4.8, J = 3.6, H,
CH) (C4), 2.14 (s, 3H, CH )(C21), 2.04 (s, 3H, CH
)(C20); 13C NMR
(CDCl ), d (ppm): 170.54 (C@O18), 170.44 (C@O14), 156.52 (C@N),
132.74–113.95 (aromatic C), 118.12 (C„N), 81.92 (CH)(C5), 61.18
(CH )(C12), 58.99 (CH )(C16), 47.51 (CH)(C4), 20.77 (CH )(C21),
20.69 (CH )(C20); Anal. Calcd for C16 (316.309): C,
2
) (C12), 4.50–4.46 (dd, J = 4.8, J = 7.2, H,
H, CH
.34 (dd, J = 8.8, J = 3.2, H, CH
J = 8.4, H, CH ) (C16), 4.00–3.95 (td, J = 5.2, J = 3.6, H, CH) (C4),
.70–2.65 (q, 2H, CH ), 2.13 (s, 3H, CH )(C21), 2.04 (s, 3H,
); C NMR (CDCl ), d (ppm):
2
) (C12), 4.47–4.42 (dd, J = 4.8, J = 7.2, H, CH
2
) (C16), 4.38–
2
2
) (C12), 4.20–4.15
4
2
) (C12), 4.16–4.11 (dd, J = 3.2,
2
2
3
3
2
CH
1
2
3
3
13
3
)(C20), 1.27–1.23 (t, 3H, CH
3
3
70.64 (C@O18), 170.48 (C@O14), 157.66 (C@N), 147.20–125.46
2
2
3
(
aromatic C), 80.89 (CH)(C5), 61.58 (CH
2
)(C12), 59.44 (CH
)(C21), 20.73 (CH
2
)(C16),
)(C20),
3
16 2 5
H N O
4
1
6
8.14 (CH)(C4), 28.78 (CH
2
), 20.82 (CH
3
3
60.75; H, 5.10; N, 8.86, Found C, 60.89; H, 5.06; N, 9.07.
5.27 (CH ); Anal. Calcd for C17
3
H21NO
5
(319.352): C, 63.94; H,
.63; N, 4.39, Found C, 64.32; H, 6.71; N, 4.50.
3.1.8. (3-(4-Nitrophenyl)-4,5-dihydroisoxazole-4,5-diyl)-
bis(methylene) diacetate(3h)
(cm 1): 1743.53
ꢁ
3.1.4. (3-(4-Bromophenyl)-4,5-dihydroisoxazole-4,5-diyl)-
270 mg (35%); mp 169–173 °C; IR (KBr),
m
1
bis(methylene) diacetate(3d)
60 mg (37%);mp 123.5–124.5 °C; IR (KBr),
(
7
2
(C@O), 1596.95 (C@N); H NMR (CDCl
J = 36.4, J = 21.6, aromatic, 2H), 7.98–7.88 (d, J = 22, J = 8, aromatic,
2H), 4.93 (s, H, CH) (C5), 4.70–4.68 (dd, J = 8.4, J = 3.6, H, CH ) (C12),
4.53–4.49 (dd, J = 4.4, J = 7.2, H, CH ) (C16), 4.37–4.34 (d, J = 10.4,
H, CH ) (C12), 4.24–4.19 (dd, J = 12, J = 7.2, H, CH ) (C16), 4.05–
4.02 (dd, J = 5.2, J = 7.2, H, CH) (C4), 2.16 (s, 3H, CH )(C21), 2.06
), d (ppm): 170.532 (C@O18),
170.44 (C@O14), 156.28 (C@N), 148.77–124.25 (aromatic C),
3
), d (ppm): 8.47–8.30 (dd,
(cm 1): 1745.46
C@O), 1730.03 (C@O), 1591.16 (C@N); H NMR (CDCl ), d (ppm):
.65–7.62 (d, J = 8.8, aromatic, 2H), 7.59–7.57 (d, J = 8.4, aromatic,
H), 4.88–4.83 (td, J = 3.2, J = 2.8, H, CH) (C5), 4.68–4.64 (dd, J = 8,
) (C12), 4.49–4.44 (dd, J = 4.8, J = 7.2, H, CH ) (C16),
.36–4.32 (dd, J = 8.4, J = 3.6, H, CH ) (C12), 4.18–4.13 (dd, J = 3.6,
J = 8.4, H, CH ) (C16), 3.99–3.94 (td, J = 5.2, J = 3.2, H, CH) (C4),
ꢁ
2
m
1
3
2
2
2
2
J = 4.4, H, CH
2
2
3
1
3
4
2
3 3
(s, 3H, CH )(C20); C NMR (CDCl
2