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BAHARFAR ET AL.
4
[
2
.5.3 | 6‐Benzoyl‐1,3‐dimethyl‐1H‐spiro
furo [2,3‐d]pyrimidine‐5,3′‐indoline]‐
,2′,4(3H,6H)‐trione (4c)
108.1, 123.2 and 124.8 (3CHAr), 125.2 (Cq), 127.4 and
128.4 (4CHAr), 129.7 and 133.8 (2CHAr), 134.2, 142.5
and 151.3 (3Cq), 158.0, 163.1 and 175.3 (3COamide),
+
●
190.7 (COketone); MS, m/z: 417 (M ).
White powder, m.p.: 244–248°C; yield (0.38 g, 95%); IR
−
1
(
(
KBr) (vmax, cm ): 3430 (NH), 2925 (C ‐H), 1709–1646
sp3
1
C=O), 1190 (Csp2‐O), 1111 (Csp3‐O); H‐NMR (400
MHz, CDCl ), δ (ppm): 3.23 and 3.58 (2 s, 6H, 2 N‐
4.5.6 | Ethyl 2‐(6‐benzoyl‐5′‐chloro‐1,3‐
dimethyl‐2,2′,4‐trioxo‐2,3,4,6‐tetrahydro‐1H‐
spiro [furo[2,3‐d]pyrimidine‐5,3′‐indolin]‐
1′‐yl) acetate (4f)
3
H
3
CH ), 6.48 (d, 1H, JHH = 7.6 Hz, CH
), 6.60 (s,
3
Oxindole
4
3
1
H, CHfuran), 6.90 (td, 1H, J = 7.6 Hz, J = 0.8 Hz,
HH HH
3
4
CH ), 6.94 (td, 1H, J = 8.0 Hz, J = 0.8 Hz, CHAr),
Ar
HH
HH
3
4
7
.01 (td, 1H, J = 7.6 Hz, J = 1.6 Hz, CH ), 7.25–
HH
HH
Ar
7
.29 (m, 2H, 2CH ),7.42–7.47 (m, 3H, 3CH ), 7.97 (br
White powder, m.p.: 216–218°C; yield (0.50 g, 95%); IR
Ar
Ar
13
−1
s, 1H, NH); C‐NMR (100 MHz, CDCl ), δ (ppm): 27.9
and 30.1 (2CH ), 58.8 (Cspiro), 91.1 (CHfuran), 109.9 and
1
(KBr) (vmax, cm ): 3434 (NH), 2924 (C ‐H), 1746–1613
3
C
sp3
1
(C=O), 1216 (Csp2‐O), 1175 (Csp3‐O); H‐NMR (400
3
3
23.2 (2CH ), 125.4 and 125.6 (2Cq), 127.5 and 128.7
MHz, CDCl ), δ (ppm): 1.33 (t, 3H, JHH = 7.2 Hz,
Ar
3
H
(
(
(
4CH ), 129.6 and 134.1 (2CH ), 139.7 (Cq), 148.0
CH ), 3.21 and 3.57 (2 s, 6H, 2 N‐CH ), 4.27 (m, 2H,
Ar
Ar
3
3
2
CH ), 151.4 and 158.1 (2Cq), 163.2, 176.9 and 179.8
OCH ), 4.28 and 4.63 (2d, 2H, J = 17.6 Hz, AB‐system,
Ar
2
HH
+
●
3
3COamide), 190.6 (COketone); MS, m/z: 403 (M ).
N‐CH ), 6.43 (d, 1H, J = 8.4 Hz, CHOxindole), 6.57 (s,
2
HH
4
furan HH Ar
1
(
2
2
H, CH
), 6.94 (d, 1H, J = 2.0 Hz, CH ), 7.037
3
4
dd, 1H, JHH = 8.4 Hz, JHH = 2.0 Hz, CH ), 7.35 (t,
Ar
4
.5.4 | 6‐Benzoyl‐5′‐chloro‐1,3‐dimethyl‐
H‐spiro [furo [2,3‐d]pyrimidine‐5,3′‐
3
3
H, J = 7.6 Hz, 2CH ), 7.48 (t, 1H, J = 7.6 Hz,
HH Ar HH
1
3
13
CH ), 7.56 (d, 2H, J = 8.8 Hz, 2CHAr); C‐NMR
Ar
HH
indoline]‐2,2′,4(3H,6H)‐trione (4d)
(
100 MHz, CDCl ), δ (ppm): 14.2, 27.9 and 30.1 (3CH ),
3
C
3
4
2.0 (N‐CH ), 58.1 (C
), 62.0 (CH ), 88.7 (Cq), 89.9
2
spiro
2
White powder, m.p.: 297–300°C; yield (0.42 g, 97%); IR
(
(
(
CHfuran), 109.3 and 125.8 (2CH ), 126.4 (Cq), 127.9
2CH ), 129.0 (Cq), 129.1 (2CH ), 129.6 (CH ), 133.7
Cq), 134.3 (CH ), 140.4 and 151.2 (2Cq), 157.9 (COester),
−
1
Ar
(
KBr) (vmax, cm ): 3452 (NH), 2955 (C ‐H), 1742–1643
sp3
1
Ar
Ar
Ar
(C=O), 1255 (Csp2‐O), 1182 (Csp3‐O); H‐NMR (400
Ar
MHz, CDCl ), δ (ppm): 3.24 and 3.58 (2 s, 6H, 2 N‐
3
H
163.5, 166.7 and 175.4 (3COamide), 190.0 (COketone); MS,
3
CH ), 6.28 (d, 1H, JHH = 9.2 Hz, CHOxindole), 6.57 (s,
3
+●
m/z: 523 (M ).
1
2
H, CHfuran), 6.90–6.93 (m, 2H, 2CH ), 7.26–7.30 (m,
Ar
H, 2CH ), 7.44–7.47 (m, 3H, 3CH ), 8.95 (br s, 1H,
Ar
Ar
13
NH); C‐NMR (100 MHz, CDCl ), δ (ppm): 28.0 and
3
C
3
1
1
1
1
0.2 (2CH ), 58.5 (Cspiro), 89.0 (Cq), 91.1 (CHfuran),
3
4
.5.7 | 6‐Benzoyl‐1′‐benzyl‐1,3‐dimethyl‐
H‐spiro [furo[2,3‐d]pyrimidine‐5,3′‐
11.2. and 125.4 (2CH ), 127.2 (Cq), 127.6 (2CH ),
Ar
Ar
1
28.3 (Cq), 128.8 (2CH ), 129.6 (CH ), 133.9 (Cq),
Ar
Ar
indoline]‐2,2′,4(3H,6H)‐trione (4g)
34.2 (CH ), 138.9 and 151.0 (2Cq), 158.5, 163.5 and
Ar
+
●
76.4 (3COamide), 190.2 (COketone); MS, m/z: 437 (M ).
White powder, m.p.: 213–215°C; yield (0.48 g, 97%); IR
−
1
(
KBr) (vmax, cm ): 3434 (NH), 2926 (C ‐H), 1722–1665
sp3
1
4
.5.5 | 6‐Benzoyl‐1,1′,3‐trimethyl‐1H‐spiro
furo [2,3‐d]pyrimidine‐5,3′‐indoline]‐
,2′,4(3H,6H)‐trione (4e)
(2C=O), 1216 (Csp2‐O), 1175 (Csp3‐O); H‐NMR (400
MHz, CDCl ), δ (ppm): 3.24 and 3.59 (2 s, 6H, 2 N‐
CH ), 4.55 and 5.11(2d, 2H, JHH = 16 Hz, AB‐system,
N‐CH ), 6.31 (d, 1H, J = 7.6 Hz, CHOxindole), 6.64 (s,
[
2
3
H
2
3
3
2
HH
White powder, m.p.: 233–237°C; yield (0.40 g, 97%); IR
1H, CHfuran), 6.87–6.91 (m, 1H, CH ), 6.94–6.99 (m,
Ar
−
1
(
KBr) (vmax, cm ): 3520 (NH), 2937 (C ‐H), 1722–1612
2H, 2CH ), 7.13–7.17 (m, 2H, 2CH ), 7.27–7.36 (m,
sp3
1
Ar
Ar
13
(C=O), 1261 (Csp2‐O), 1194 (Csp3‐O); H‐NMR (400
7H, 2CH ), 7.41–7.46 (m, 1H, CH ); C‐NMR (100
Ar
Ar
MHz, CDCl ), δ (ppm): 3.10, 3.20 and 3.58 (3 s, 9H,
MHz, CDCl ), δ (ppm): 28.0 and 30.1 (2 N‐CH ), 44.6
3
H
3
C
3
3
3
N‐CH ), 6.42 (d, 1H, J = 8.0 Hz, CHOxindole), 6.58
(N‐CH ), 58.3 (Cspiro), 89.4 (Cq), 91.1 (CHfuran), 109.3
3
HH
2
(
s, 1H, CHfuran), 6.92–6.98 (m, 2H, 2CH ), 7.08 (td, 1H,
and 123.3 (2CH ), 125.1 and 125.2 (2Cq), 127.1 and
Ar
Ar
3
4
JHH = 6.4 Hz, JHH = 2 Hz, CH ), 7.22–7.25 (m, 2H,
127.5 (4CH ), 127.6 (Cq), 128.6 and 128.9 (4CH ),
Ar
Ar
Ar
2
CH ), 7.28–7.31 (m, 2H, 2CH ), 7.49 (m, 1H, CH );
129.5 and 133.9 (2CH ), 134.2 and 134.7 (2Cq), 141.9
Ar
Ar
Ar
Ar
1
3
C‐NMR (100 MHz, CDCl ), δ (ppm): 26.8 and 27.9,
and 151.3 (2Cq), 157.9, 163.0 and 175.6 (3COamide),
3
C
+
●
3
0.1 (3CH ), 58.3 (Cspiro), 89.0 (Cq), 91.7 (CHfuran),
190.7 (COketone); MS, m/z: 493 (M ).
3