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13. Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.;
Tatchell, A. R. Vogel’s Textbook of Practical Organic
Chemistry, 5th ed.; Longman Scientific & Technical: New
York, 1991; p. 1276.
14. Lima, L. M.; Barreiro, E. J.; Fraga, C. A. M. Synth.
Commun. 2000, 30, 3291.
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C. A. M. Synth. Commun. 1999, 29, 263.
17. The analytical results for C, H, N of the compounds 4a–d,
and 1.78 Hz, H60); 7.38 (d, J = 8.13 Hz, H20 0 and H60 0);
7.39 (m, H40); 7.79 (m, H5 and H6); 7.94 (d, J = 8.00 Hz,
H30 0 and H50 0); 7.95 (m, H4 and H7); 13C NMR (50 MHz,
CDCl3) d: 51.90 (RCO2CH3); 69.57 (ROCH2R); 113.32
(C30); 120.63 (C10); 121.30 (C50); 126.38 (C20 0 and C60 0);
123.46 (C7 and C4); 129.35 (C40 0); 129.59 (C30 0 and C50 0);
129.99 (C40); 130.41 (C60); 131.98 (C7a and C3a); 134.06
(C6 and C5); 141.51 (C10 0); 153.93 (C20); 166.57
(RCO2CH3); 167.17 (C1 and C3); Compound 5a: mp:
139–140 °C; 1H NMR (200 MHz, CDCl3) d: 2.58 (m,
CH2S); 3.73 (m, CH2N); 8.13 (d, J = 8.20 Hz, H30); 7.29
(dt, J = 7.78 Hz and 8.70 Hz, H50); 7.45 (d, J = 8.70 Hz,
H60); 7.22 (dt, J = 7.78 Hz and 8.20 Hz, H40); 7.85 (m, H5
and H6); 7.91 (m, H4 and H7); 13C NMR (50 MHz,
CDCl3) d: 28.02 (CH2S); 28.30 (CH2S); 44.99 (CH2N);
49.68 (CH2N); 129.83 (C30); 141.52 (C10); 131.60 (C50);
123.92 (C7 and C4); 121.89 (C60); 126.88 (C40); 131.98 and
137.03 (C7a and C3a); 134.60 (C6 and C5); 122.83 (C20);
165,61 (ArCONR2); 166.85 and 167.94 (C1 and C3);
Compound 5b: mp: 159–160 °C;1H NMR (200 MHz,
CDCl3) d: 2.53 (m, CH2S); 3.70 (m; CH2N); 6.01 (s,
OCH2O); 6.63 (s, H30); 7.08 (s, H60); 7.86 (m, H5 and H6);
7.89 (m, H4 and H7); 13C NMR (50 MHz, CDCl3) d: 28.06
(CH2S); 29.10 (CH2S); 44.50 (CH2N); 49.02 (CH2N);
100.61 (OCH2O); 107.88 (C30); 135.48 (C10); 149.74 (C50);
123.71 (C7 and C4); 104.89 (C60); 148.88 (C40); 131.98 and
137.83 (C7a and C3a); 137.90 (C6 and C5); 119.11 (C20);
164,91 (ArCONR2); 166.80 and 166.95 (C1 and C3);
Compound 6a: brownish oil; 1H NMR (200 MHz, CDCl3)
d: 1.51 (d; J = 6.76 Hz, ROCH(CH3)CONR); 2.60 (m;
CH2S); 3.70 (m; CH2N); 4.90 (q, J = 6.77 Hz,
ROCH(CH3)CONR); 7.02 (d, J = 8.20 Hz, H30); 7.18
(dt, J = 7.53 Hz and 7.58 Hz, H50); 7.36 (d, J = 8.65 Hz,
H60); 7.44 (dt, J = 7.58 Hz and 8.70 Hz, H40); 7.85 (m; H5
and H6); 7.94 (m; H4 and H7); 13C NMR (50 MHz,
CDCl3) d: 18.44 (ROCH(CH3)CONR); 27.44 (CH2S);
28.31 (CH2S); 44.87 (CH2N); 48.26 (CH2N); 72.85
(ROCH(CH3)CONR); 113.01 (C30); 120.55 (C10); 122.70
(C50); 124.45 (C7 and C4); 126.02 (C60); 130.83 (C40);
131.98 and 132.05 (C7a and C3a); 134.61 (C6 and C5);
151.95 (C20); 166,28 (ArOCH(CH3)CONR); 167.15 and
168.21 (C1 and C3); Compound 6b: brownish oil; 1H
NMR (200 MHz, CDCl3) d: 1.53 (d, J = 6.70 Hz,
ROCH(CH3)CONR); 2.77 (m, CH2S); 2.81 (m, CH2 S);
3.68 (m, CH2N); 3.90 (m, CH2N); 4.88 (q, J = 6.70 Hz,
ROCH(CH3)CONR); 7.09 (d, J = 8.10 Hz, H30); 8.08 (s,
H60); 8.12 (d, J = 8.10 Hz, H40); 7.93 (m, H5 and H6); 7.97
(m, H4 and H7); 13C NMR (50 MHz, CDCl3) d: 19.40
(ROCH(CH3)CONR); 27.40 (CH2S); 27.45 (CH2S); 27.85
(CH2S); 28.05 (CH2S); 44.85 (CH2N); 48.26 (CH2N);
50.81(CH2N); 51.05 (CH2N); 73.01 (ROCH(CH3)CONR);
115.43 (C30); 131.12 (C10); 139.60 (C50); 124.72 (C7 and
C4); 115.95 (C60); 126.77 (C40); 131.98 and 134.53 (C7a
and C3a); 134.60 (C6 and C5); 154.10 (C20);
168.01(ArOCH(CH3)CONR); 167.11 and 167.23 (C1 and
C3).
5a,b, and 6a,b were within
values.
0.4% of calculated
18. Physical and spectroscopic data: Compound 4a: mp: 137–
138 °C; 1H NMR (200 MHz, CDCl3) d: 1.15 (t,
J = 7.14 Hz, ROCH2CO2CH2CH3); 4.15 (q, J = 7.14 Hz,
ROCH2CO2CH2CH3); 4.62 (s, ROCH2CO2CH2CH3);
6.97 (dd, J = 8.33 Hz and 1.10 Hz, H30); 7.15 (dt,
J = 7.60 Hz and 7.60 Hz, H50); 7.32 (dd, J = 7.78 Hz and
1.74 Hz, H60); 7.42 (dt, J = 8.30 Hz and 7.51 Hz, H40);
7.78 (m, H5 and H6); 7.95 (m, H4 and H7); 13C NMR
(50 MHz, CDCl3) d: 14.08 (ROCH2CO2CH2CH3); 61.42
(ROCH2CO2CH2CH3); 66.50 (ROCH2CO2CH2CH3);
113.84 (C30); 121.37 (C10); 122.34 (C50); 123.81 (C7
and C4); 130.35 (C40); 130.65 (C60); 132.41 (C7a and
C3a); 134.26 (C6 and C5); 154.08 (C20); 167.33 (C1
and C3); 168.38 (ROCH2CO2CH2CH3); Compound
4b: mp: 101–102 °C; 1H NMR (200 MHz, CDCl3) d:
1.42 (d, J = 6.80 Hz, ROCH(CH3)CO2CH3); 3.59
(s, ROCH(CH3)CO2CH3); 4.69 (q, J = 6.80 Hz,
ROCH(CH3)CO2CH3); 6.86 (d, J = 8.17 Hz, H30); 7.05
(dt, J = 7.44–7.70 Hz, H50); 7.23 (dd, J = 7.71–1.50 Hz,
H60); 7.32 (dt, J = 8.20–7.48 Hz, H40); 7.72 (m, H5–H6);
7.83 (m; H4–H7); 13C NMR (50 MHz, CDCl3) d: 18.47
(ROCH(CH3)CO2CH3); 52.33 (ROCH(CH3)CO2CH3);
73.99 (ROCH(CH3)CO2CH3); 114.23(C30); 121.42 (C10);
122.08 (C50); 123.59–123.70 (C7–C4); 130.30 (C60); 130.54
(C40); 132.15–132.33 (C3a–C7a); 134.19 (C6–C5); 153.79
(C20); 167.14–167.23 (C1–C3); 171.99 (ROCH(CH3)-
CO2CH3); Compound 4c: mp: 125–126 °C; 1H NMR
(200 MHz, CDCl3) d: 1.56 (d, J = 6.76 Hz, ROCH(CH3)-
CO2H); 4.94 (q, J = 6.77 Hz, ROCH(CH3)CO2CH3); 5.75
(s, CO2 H); 7.01 (d, J = 8.20 Hz, H30); 7.16 (dt,
J = 7.53 Hz and 7.58 Hz, H50); 7.35 (d, J = 8.65 Hz,
H60); 7.42 (dt, J = 7.58 Hz and 8.70 Hz, H40); 7.83 (m,
H5 and H6); 7.97 (m, H4 and H7); 13C NMR (50 MHz,
CDCl3)
d:
18.48
(ROCH(CH3)CO2H);
73.25
(ROCH(CH3)CO2H); 113.03 (C30); 120.52 (C10); 122.60
(C50); 124.22 (C7 and C4); 125.92 (C60); 130.83 (C40);
131.98 and 132.03 (C7a and C3a); 134.83 (C6 and C5);
151.92 (C20); 167.11 and 168.24 (C1 and C3); 173.15
(ROCH(CH3)CO2H); Compound 4d: mp: 165–167 °C;1H
NMR (200 MHz, CDCl3) d: 3.83 (s; ArCO2CH3); 5.19 (s,
ROCH2Ar); 7.02 (dd, J = 8.30 Hz and 1.18 Hz, H30); 7.12
(dt, J = 7.62 Hz and 7.68 Hz, H50); 7.32 (dd, J = 7.87 Hz