1
Supporting Information
Synthesis of ß-phthalimido-alcohols via regioselective ring opening of epoxide by using reusable basic magnetic nano particles and their
biological investigation
Mohammad Ali Zolfigol,*a Ahmad Reza Moosavi-Zare,*b Mahmoud Zarei, a Abdolkarim Zare,c
Ehsan noroozizadeh,a Roya Karamiand and Mostafa Asadbegyd
aDepatment of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan
6517838683, Tel: +988138282807, Fax: +988138380709 Iran. E-Mail: [email protected] &
[email protected]
Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2016
2
N
O
OOH
2-(2-hydroxy-2-methylpropyl)isoindoline-1,3-dione (1)
Colorless solid; mp 103-105 °C; IR (KBr) νmax (cm-1): 1697, 1774, 2973, 3444, 3526 ; 1H NMR
(CDCl3): δ 1.21 (6H, S), 2.83 (1H, S), 3.76 (2H, S), 7.28 (1H, S), 7.72-7.76 (2H, d, J = 6.9), 7.84-
7.89 (2H, dd, J = 3.2, 2.4 Hz); 13C NMR (CDCl3): δ 27.4, 49.1, 71.5, 122.5, 131.4, 134.2, 169.2;
MS m/z (%): 219 (M+).
N
O
OHO
3
117
136
144
174
209219
102.3106.2
109.3112.4
117.3122.3
125.3130.2
135.3138.3
140.3145.3
150.2153.3
161.3168.3
173.2177.4
186.2194.4
197.3204.2
209.3212.2 215
2180
20000
40000
60000
80000
100000
120000
140000
160000 203
N
O
OHO
N
O
OHO
N
O
OHO
4
2-(2-hydroxy-3-phenoxypropyl)isoindoline-1,3-dione (2)
Colorless solid; mp 104-106 °C; IR (KBr) νmax (cm-1):1710, 1766, 2934, 3448, 3572; 1H NMR
(CDCl3): δ 3.04 HZ (s, 1H); 3.94-3.98 Hz (q, 1H); 4.02-4.1 Hz (m, 3H); 4.31-4.34 Hz (m, 1H),
6.9-6.93 Hz (d, 2H), 6.90-7.0 Hz (m, 3H); 7.26-7.28 Hz (m, 2H); 7.29-7.31 Hz (m, 2H); 7.73-7.88
Hz (m, 2H); 13C NMR (CDCl3): δ 41.26, 68.76, 69.02, 114.51, 114.61, 121.31, 123.37, 129.48,
129.52, 131.96, 134.16, 158.36, 168.76; MS m/z (%): 297 (M+).
N
O
O OHO
N
O
O OHO
5
4 0 6 0 8 0 1 0 0 1 2 0 1 4 0 1 6 0 1 8 0 2 0 0 2 2 0 2 4 0 2 6 0 2 8 00
2 0 0 0 0 0
4 0 0 0 0 0
6 0 0 0 0 0
8 0 0 0 0 0
1 0 0 0 0 0 0
1 2 0 0 0 0 0
1 4 0 0 0 0 0
1 6 0 0 0 0 0
1 8 0 0 0 0 0
2 0 0 0 0 0 0
2 2 0 0 0 0 0
2 4 0 0 0 0 0
m / z - - >
A b u n d a n c e
S c a n 6 6 ( 0 . 7 3 7 m i n ) : 3 0 0 1 2 3 2 0 . D1 8 6
1 6 0
2 0 4
7 7
9 4
1 3 35 0
6 51 0 5 2 9 71 7 2
1 4 81 1 7 2 7 92 5 12 3 62 2 2 2 6 4
N
O
O OHO
N
O
O OHO
N
O
O OHO
6
N
O
O
HO
2-(2-hydroxy-2-phenylethyl)isoindoline-1,3-dione (3)
Colorless solid; mp 159-161 °C; IR (KBr) νmax (cm-1): 1772, 1688, 3037, 3454 ; 1H NMR (CDCl3): δ 3.07 (s, 1H); 3.91-4.05 (m, 2H); 5.06-5.09 (s, 1H); 7.28-7.47 (m, 5H); 7.71-7.85 (m, 4H); 13C NMR (CDCl3): δ45.73, 72.54, 123.45, 125.89, 128.09, 128.54, 131.87, 134.12, 141.03, 168.78; MS m/z (%): 267 (M+).
N
O
O
HO
N
O
O
HO
7
4 0 6 0 8 0 1 0 0 1 2 0 1 4 0 1 6 0 1 8 0 2 0 0 2 2 0 2 4 0 2 6 00
2 0 0 0 0 0
4 0 0 0 0 0
6 0 0 0 0 0
8 0 0 0 0 0
1 0 0 0 0 0 0
1 2 0 0 0 0 0
1 4 0 0 0 0 0
1 6 0 0 0 0 0
1 8 0 0 0 0 0
2 0 0 0 0 0 0
2 2 0 0 0 0 0
2 4 0 0 0 0 0
2 6 0 0 0 0 0
2 8 0 0 0 0 0
3 0 0 0 0 0 0
3 2 0 0 0 0 0
m / z - - >
A b u n d a n c e
S c a n 8 1 ( 0 . 8 6 4 m i n ) : 3 0 0 1 2 3 2 1 . D1 6 1
7 7
1 0 4
5 01 3 2
1 1 7 2 5 0
2 6 71 4 7
6 3 9 1 2 3 61 9 0 2 0 4 2 2 51 7 9 2 1 4
N
O
O
HO
N
O
O
HO
8
N
O
O HO
2-(2-hydroxycyclooctyl)isoindoline-1,3-dione (4)
Colorless solid; mp 234-238 °C; IR (KBr) νmax (cm-1): 1751, 1774, 2717, 3061, 3199; 1H NMR
(CDCl3): δ 0.95-0.98 (m, 2H); 1.27-1.46 (m, 6H); 1.64-1.72 (m, 2H); 3.71 (t, J = 6.9, 2H); 7.71-
7.91 (m, 4H); 13CNMR (CDCl3): δ13.64, 20.08, 29.07, 30.65, 31.43, 123.14, 123.63, 131.83,
13434, 168.78; MS m/z (%): 273 (M+).
N
O
OHO
10
152.4
161
195
213 236
260
273
150.
515
5.4
159.
516
2.5
166.
617
0.4
173.
417
7.5
181.
418
5.5
188.
519
1.5
196.
520
0.5
203.
620
6.5
209.
521
2.5
215.
621
8.5
221.
622
4.6
227.
623
0.5
233.
123
7.6
240.
624
3.2
245.
524
8.5
251.
625
4.7
257.
626
1.5
264.
626
7.6
269.
727
1.7
273.
6
0
10000
20000
30000
40000
50000
60000
70000
80000
90000
100000
N
O
O
N
O
OOH
OH
(2.2’-(2,7- dihydroxyoctane-1,8-diyl)diisoindoline-1,3-dione) (5)
Colorless solid; mp 203-205 °C; IR (KBr) νmax (cm-1): 1713, 1771, 2932, 3319, 3380; 1H NMR (DMSO-d6): δ 1.27-1.3 (d, J = 13.2, 2H); 1.39-1.43 (d, J = 10.4, 2H); 3.43-3.56 (m, 3H); 3.73 (s, 1H); 4.84-4.85 (d, J=5.2, 1H); 7.81-7.84 (m, 4H); 13C NMR (DMSO-d6): δ25.66, 34.95, 44.65, 67.61, 123.35, 132.22, 134.7, 168.53; MS m/z (%): 437 (M+,1).
N
O
OHO
11
305 339379
401
419
437
300.
130
4.1
308.
731
3.3
318.
232
2.2
325.
133
0.3
334.
233
6.9
340.
134
334
7.3
353.
335
7.1
361.
836
636
9.2
372.
137
5.2
379.
838
4.3
387.
239
1.4
396.
840
1.3
405.
641
2.3
417.
342
2.8
428.
843
6.4
0
2000
4000
6000
8000
10000
12000
14000
16000
18000
20000
N
O
O
N
O
OOH
OH
N
O
O
N
O
OOH
OH
N
O
O
N
O
OOH
OH
12
HO
N
O
O
2-(2-hydroxy-3-phenylpropyl)isoindoline-1,3-dione (6)
Colorless solid; mp 121-123 °C; IR (KBr) νmax (cm-1): 1711, 1753, 2993, 3450; 1H NMR (DMSO-d6): δ 3.64-3.75 (m, 2H); 3.95 (d, J = 7.5, 2H); 4.15 (d, J = 4.2, 1H); 5.39 (d, J = 3.9, 1H); 6.84-6.92 (m, 2H); 7.23-7.29 (m, 2H); 7.8-7.89 (m, 4H): 13C NMR (DMSO-d6): δ 42.94, 67.6, 71.4, 115.97, 122.2, 124.2, 131.03, 133.3, 134.1, 135.8, 159.9; MS m/z (%): 281 (M+).
N
O
O
N
O
OOH
OH
HO
N
O
O
13
4 0 6 0 8 0 1 0 0 1 2 0 1 4 0 1 6 0 1 8 0 2 0 0 2 2 0 2 4 0 2 6 0 2 8 0 3 0 00
5 0 0 0 0 0
1 0 0 0 0 0 0
1 5 0 0 0 0 0
2 0 0 0 0 0 0
2 5 0 0 0 0 0
3 0 0 0 0 0 0
3 5 0 0 0 0 0
m / z -->
A b u n d a n c e
S c a n 8 5 (0 . 8 9 8 m in ) : 3 0 0 1 2 3 1 7 . D1 8 6
2 0 4
1 6 0
2 9 8
7 79 4 1 3 3
1 7 25 0 1 0 5 2 7 96 5 1 4 81 1 7 3 1 02 5 12 3 62 2 4 2 6 4
HO
N
O
O
HO
N
O
O
HO
N
O
O
14
HOO
N
O
O
2-(2-hydroxy-2-isopropoxyethyl)isoindoline-1,3-dione (7)
Colorless solid; mp 125-128 °C; IR (KBr) νmax (cm-1): 1715, 1774, 2972, 3202, 3469; 1H NMR (DMSO-d6): δ 0.99-1.02 (s, 6H); 3.28-3.49 (m, 3H); 3.65-3.7 (m, 1H); 3.92-3.95 (m, 1H); 7.49-7.5 (m, 4H): 13C NMR (DMSO-d6): δ 23, 124.17, 134.16, 135.08, 170 ; MS m/z (%): 249 (M+).
HOO
N
O
O
HOO
N
O
O
15
HOO
N
O
O
HOO
N
O
O
16
SOHOO
O
N
O
O
3-(1,3-dioxoisoindolin-2-yl)-2-hydroxypropyl 4-methylbenzenesulfonate (8)
Colorless solid; mp 132-135 °C; IR (KBr) νmax (cm-1): 1716, 1774, 3027, 3201, 3456; 1H NMR (CDCl3): δ 1.25 (s, 3H); 2.46 (s, 3H); 4.04 (s, 2H); 7.36 (d, J = 5.1, 2H); 7.76-7.82 (m, 4H); 7.87-7.88 (m, 2H); MS m/z (%): 376 (M+, 1).
SOHOO
O
N
O
O
SOHOO
O
N
O
O
17
215
236
281
313 339
368
376
200.
620
5.5
210.
921
5.4
220.
622
4.6
229.
623
3.4
238.
724
2.6
246.
725
1.8
256.
726
1.7
266.
627
1.7
275.
827
9.7
284.
828
8.7
292.
929
6.8
301.
530
6.1
311.
131
5.9
320.
632
5.8
329.
833
3.9
337.
934
2.7
347.
835
3.1
357.
636
1.7
364.
536
8.9
372.
9
0
5000
10000
15000
20000
25000
30000
HO Cl
N
O
O
2-(3-chloro-2-hydroxypropyl)isoindoline-1,3-dione (9)
Colorless solid; mp 173-176 °C; IR (KBr) νmax (cm-1): 1714, 1752, 1774, 2716, 3062, 3206, 3487; 1H NMR (DMSO-d6): δ 3.54-3.57 (m, 2H); 3.63-3.66 (m, 2H); 4.2 (s, 2H); 5.2 (s, OH); 7.8-7.84 (m, 4H); 13C NMR (DMSO-d6): δ 43.5, 66.6, 124.4, 124.5, 133.2, 134.1, 135.8, 135.9, 159, 161 ; MS m/z (%): 239 (M+).
SOHOO
O
N
O
O
18
HO Cl
N
O
O
HO Cl
N
O
O
HO Cl
N
O
O
19
103
133
160
190 222
239
103.
111
0.4
117.
112
3.1
125
132.
213
5.3
137.
514
1.2
142.
914
5.2
147.
415
1.5
164.
816
6.6
169.
517
1.8
176.
717
8.7
182.
318
6.3
190.
819
4.1
196.
720
7.1
210.
121
4.4
216.
422
6.6
228.
923
2.1
236.
3
0
100000
200000
300000
400000
500000
600000
700000
800000
900000
1000000
N
O
O
OH
Cl
(R)-2-(2-(3-chlorophenyl)-2-hydroxyethyl)isoindoline-1,3-dione (10)
Colorless solid; mp 109-112 °C; IR (KBr) νmax (cm-1): 1714, 1774, 2937, 3447; 1H NMR (DMSO-
d6): δ 3.62-3.79 (m, 2H); 4.89-4.91 (t, 1H); 5.84 (s, OH); 7.31-7.36 (t, 3H); 7.41(s, 1H); 7.82-7.86
(t, 4H); 13C NMR (DMSO-d6): δ 45.6, 69.3, 123.3, 123.4, 126.2, 127.8, 130.5, 132.0, 133.0,
133.4, 134.7, 134.8, 145.4, 168.2, 169.7.
HO Cl
N
O
O
20
N
O
O HO
Cl
N
O
O HO
Cl
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