ACCEPTED MANUSCRIPT
1
1599 (C=N); H NMR (400 MHz, CDCl3), δ (ppm) : 7.58-7.56 (d, J=8, aromatic, 2H), 7.25-
7.23 (d, J=8, aromatic, 2H), 4.92-4.87 (m, 7CH2, 10CH, 2H), 4.70-4.68 (d, J= 6.0, 7CH2, H),
4.40-4.35 (dd, J= 4, J= 13.6, 9CH2, H), 4.14-4.09 (q, J= 6.8, J= 12.4, 5CH2, H), 4.03-3.97 (m,
4CH, 9CH, 2H), 3.96-3.92 (dd, J= 3.6, J= 12.2, 5CH2, H); 2.39 (s, CH3,3H); 13C NMR
(CDCl3), δ (ppm) : 157.36 (C=N), 140.43-125.90 (aromatic C), 98.37 (7CH2), 83.49 (10CH),
68.62 (9CH2), 66.43 (5CH2), 52.07 (4CH), 21.43 (CH3); HRMS m/z (ESI/TOF/MS, [M+H]+
)calcd for C13H16NO3: 234.1132, Found 234.1131.
3.1.3. 3-(4-ethylphenyl)-3a,4,8,8a-tetrahydro-1,3-dioxepino[5,6-d] [1,2] isoxazole (2c) Yield
o
30 %; mp 114.6-115.2 C; IR (KBr), ν (cm-1): 2960 (C-H), 2911 (C-H), 2874 (C-H), 1599
(C=N); 1H NMR (400 MHz, CDCl3), δ (ppm) : 7.60-7.58 (d, J=8.0, aromatic, 2H), 7.27-7.25
(d, J=8.0, aromatic, 2H), 4.93-4.88 (m, 7CH2, 10CH, 2H), 4.70-4.68 (d, J= 6.0, 7CH2, H),
4.40-4.36 (dd, J= 3.6, J= 13.6, 9CH2, H), 4.15-4.10 (q, J= 6.8, J= 12.2, 5CH2, H), 4.03-3.98
(m, 4CH, 9CH2, 2H), 3.97-3.93 (dd, J= 3.6, J= 12, 5CH2, H), 2.72-2.66 (q, J= 7.6, J= 16.7,
CH2, 2H), 1.28-1.24 (t, J= 7.6, J= 8.4, CH3, 3H); 13C NMR (CDCl3), δ (ppm) : 157.38 (C=N),
146.69-126.11 (aromatic C), 98.37 (7CH2), 83.50 (10CH), 68.61 (9CH2), 66.46 (5CH2), 52.07
(4CH), 21.77 (CH2), 15.31 (CH3); HRMS m/z (ESI/TOF/MS, [M+H]+ )calcd for C14H18NO3:
248.1288, Found 248.1287.
3.1.4. 3-(4-fluorophenyl)-3a,4,8,8a-tetrahydro-1,3-dioxepino[5,6-d] [1,2] isoxazole (2d)
o
Yield 30 %; mp 150-151.4 C; IR (KBr), ν (cm-1): 2956 (C-H), 2917 (C-H), 2870 (C-H),
1
1600 (C=N); H NMR (400 MHz, CDCl3), δ (ppm) : 7.68-7.64 (td, J=5.2, J=8.6, aromatic,
2H), 7.14-7.10 (t, J=8.8, J=9.4, aromatic, 2H), 4.94-4.89 (m, 7CH2, 10CH, 2H), 4.66-4.65 (d,
J= 6, 7CH2, H), 4.41-4.37(dd, J= 3.6, J= 13.8, 9CH2, H), 4.16-4.12 (q, J= 6.4, J= 12.4, 5CH2,
H), 4.01-3.96 (m, 4CH, 9CH, 2H), 3.94-3.90 (dd, J= 3.6, J= 12.6, 5CH2, H); 13C NMR
(CDCl3), δ (ppm) : 157.47 (C=N), 128.96-116.24 (aromatic C), 98.45 (7CH2), 83.66 (10CH),
68.85 (9CH2), 66.439 (5CH2), 52.08 (4CH); HRMS m/z (ESI/TOF/MS, [M+H]+ )calcd for
C12H13FNO3: 238.0881, Found 238.0883.
3.1.5. 3-(4-chlorophenyl)-3a,4,8,8a-tetrahydro-1,3-dioxepino[5,6-d] [1,2] isoxazole (2e)
o
Yield 31 %; mp 165.5-165.8 C; IR (KBr), ν (cm-1): 2986 (C-H), 2963 (C-H), 2911 (C-H),
1
1595 (C=N); H NMR (400 MHz, CDCl3), δ (ppm) : 7.62-7.60 (d, J=8.0, aromatic, 2H),
7.42-7.40 (d, J=8.4, aromatic, 2H), 4.94-4.91 (m, 7CH2, 10CH, 2H), 4.66-4.64 (d, J= 6.0,
7CH2, H), 4.42-4.38 (dd, J= 2.8, J= 13.6, 9CH2, H), 4.16-4.11 (q, J= 6.8, J= 12.9, 5CH2, H),
4.01-3.98 (d, J= 12.4, 4CH, H), 4.00-3.95 (d, J= 16.8, 9CH2, H), 3.93-3.90 (d, J= 12.8, 5CH2,
13
H); C NMR (CDCl3), δ (ppm) : 156.48 (C=N), 136.16-127.32 (aromatic C), 98.46 (7CH2),
5