Chem. J. Chinese Universities ›› 2016, Vol. 37 ›› Issue (10): 1804.doi: 10.7503/cjcu20160410
• Organic Chemistry • Previous Articles Next Articles
ZHANG Xiaopeng*(), LI Zhengwei, WANG Yan, NIU Xueli, ZHANG Guisheng
Received:
2016-06-07
Online:
2016-10-10
Published:
2016-08-23
Contact:
ZHANG Xiaopeng
E-mail:zhangxiaopengv@sina.com
Supported by:
CLC Number:
TrendMD:
ZHANG Xiaopeng, LI Zhengwei, WANG Yan, NIU Xueli, ZHANG Guisheng. Selenium-catalyzed Carbonylation of 4-Aminopyridine with Nitro Aromatics to 4-Pyridinylureas†[J]. Chem. J. Chinese Universities, 2016, 37(10): 1804.
Nitro compd. | Compd. | m. p./℃(lit.) | CAS No. |
---|---|---|---|
Nitrobenzene | 2a | 164—165(166—167[ | 1932-35-0 |
1-Chloro-2-nitrobenzene | 2b | 173—175(174—176[ | 20949-44-4 |
1-Chloro-3-nitrobenzene | 2c | 214—216(211—214[ | 13208-37-2 |
1-Chloro-4-nitrobenzene | 2d | 243—245(242—243[ | 13208-60-1 |
1-Bromo-4-nitrobenzene | 2e | 259—261(248—250[ | 13142-16-0 |
1-Methyl-4-nitrobenzene | 2f | 188—189(188—189[ | 13256-77-4 |
1-Methoxy-4-nitrobenzene | 2g | 175—176(175—176[ | 20949-48-8 |
4-Nitrophenol | 2h | 240—241 | 69424-45-9 |
1-Nitronaphthalene | 2i | 247—248 | 13256-93-4 |
Table 1 Melting points and CAS number for compounds 2a—2i
Nitro compd. | Compd. | m. p./℃(lit.) | CAS No. |
---|---|---|---|
Nitrobenzene | 2a | 164—165(166—167[ | 1932-35-0 |
1-Chloro-2-nitrobenzene | 2b | 173—175(174—176[ | 20949-44-4 |
1-Chloro-3-nitrobenzene | 2c | 214—216(211—214[ | 13208-37-2 |
1-Chloro-4-nitrobenzene | 2d | 243—245(242—243[ | 13208-60-1 |
1-Bromo-4-nitrobenzene | 2e | 259—261(248—250[ | 13142-16-0 |
1-Methyl-4-nitrobenzene | 2f | 188—189(188—189[ | 13256-77-4 |
1-Methoxy-4-nitrobenzene | 2g | 175—176(175—176[ | 20949-48-8 |
4-Nitrophenol | 2h | 240—241 | 69424-45-9 |
1-Nitronaphthalene | 2i | 247—248 | 13256-93-4 |
Compd. | 1H NMR(DMSO-d6, 400 MHz), δ | 13C NMR(DMSO-d6, 100 MHz), δ |
---|---|---|
2h | 9.15(s, 1H), 8.98(s, 1H), 8.52(s, 1H), 8.31(d, J=5.2 Hz, | 153.49, 152.75, 150.50, 147.23, 130.86, |
2H), 7.39(d, J=6.1 Hz, 2H), 7.21(d, J=8.8 Hz, 2H), 6.69 | 121.34, 115.71, 112.58 | |
(d, J=8.8 Hz, 2H) | ||
2i | 9.69(s, 1H), 9.13(s, 1H), 8.39(d, J=5.8 Hz, 2H), 8.14 | 153.20, 150.66, 147.12, 134.23, 134.18, |
(d, J=8.4 Hz, 1H), 7.96(td, J=7.9, 1.1 Hz, 2H), 7.70(d, | 128.86, 126.87, 126.46, 126.33, 126.27, | |
J=8.2 Hz, 1H), 7.63—7.48(m, 5H) | 124.18, 122.00, 118.88, 112.73 |
Table 2 1H NMR and 13C NMR data for compounds 2h—2i
Compd. | 1H NMR(DMSO-d6, 400 MHz), δ | 13C NMR(DMSO-d6, 100 MHz), δ |
---|---|---|
2h | 9.15(s, 1H), 8.98(s, 1H), 8.52(s, 1H), 8.31(d, J=5.2 Hz, | 153.49, 152.75, 150.50, 147.23, 130.86, |
2H), 7.39(d, J=6.1 Hz, 2H), 7.21(d, J=8.8 Hz, 2H), 6.69 | 121.34, 115.71, 112.58 | |
(d, J=8.8 Hz, 2H) | ||
2i | 9.69(s, 1H), 9.13(s, 1H), 8.39(d, J=5.8 Hz, 2H), 8.14 | 153.20, 150.66, 147.12, 134.23, 134.18, |
(d, J=8.4 Hz, 1H), 7.96(td, J=7.9, 1.1 Hz, 2H), 7.70(d, | 128.86, 126.87, 126.46, 126.33, 126.27, | |
J=8.2 Hz, 1H), 7.63—7.48(m, 5H) | 124.18, 122.00, 118.88, 112.73 |
Entry | Temperature/℃ | Time/h | Solvent | Base | Yieldb(%) |
---|---|---|---|---|---|
1 | 90 | 5 | DMF | Et3N | 13(36)c |
2 | 110 | 5 | DMF | Et3N | 44(12)c |
3 | 130 | 5 | DMF | Et3N | 78 |
4 | 150 | 5 | DMF | Et3N | 76 |
5 | 130 | 3 | DMF | Et3N | 50 |
6 | 130 | 4 | DMF | Et3N | 73 |
7 | 130 | 6 | DMF | Et3N | 78 |
8 | 130 | 5 | Acetone | Et3N | 16 |
9 | 130 | 5 | Ethylacetate | Et3N | 27 |
10 | 130 | 5 | THF | Et3N | 22 |
11 | 130 | 5 | DMSO | Et3N | 62 |
12 | 130 | 5 | Toluene | Et3N | 67 |
13 | 130 | 5 | DMF | Trace | |
14 | 130 | 5 | DMF | KOH | 58 |
15 | 130 | 5 | DMF | NaOH | 28 |
16 | 130 | 5 | DMF | Na2CO3 | Trace |
17 | 130 | 5 | DMF | K2CO3 | Trace |
18 | 130 | 5 | DMF | DBU | 31 |
19 | 130 | 5 | DMF | DIPEA | 70 |
Table 3 Optimization of reaction conditionsa
Entry | Temperature/℃ | Time/h | Solvent | Base | Yieldb(%) |
---|---|---|---|---|---|
1 | 90 | 5 | DMF | Et3N | 13(36)c |
2 | 110 | 5 | DMF | Et3N | 44(12)c |
3 | 130 | 5 | DMF | Et3N | 78 |
4 | 150 | 5 | DMF | Et3N | 76 |
5 | 130 | 3 | DMF | Et3N | 50 |
6 | 130 | 4 | DMF | Et3N | 73 |
7 | 130 | 6 | DMF | Et3N | 78 |
8 | 130 | 5 | Acetone | Et3N | 16 |
9 | 130 | 5 | Ethylacetate | Et3N | 27 |
10 | 130 | 5 | THF | Et3N | 22 |
11 | 130 | 5 | DMSO | Et3N | 62 |
12 | 130 | 5 | Toluene | Et3N | 67 |
13 | 130 | 5 | DMF | Trace | |
14 | 130 | 5 | DMF | KOH | 58 |
15 | 130 | 5 | DMF | NaOH | 28 |
16 | 130 | 5 | DMF | Na2CO3 | Trace |
17 | 130 | 5 | DMF | K2CO3 | Trace |
18 | 130 | 5 | DMF | DBU | 31 |
19 | 130 | 5 | DMF | DIPEA | 70 |
Entry | Product | Yieldb(%) | Entry | Product | Yieldb(%) |
---|---|---|---|---|---|
1 | 78 | 7 | 85 | ||
2a | 2g | ||||
2 | 47 | 8 | 81 | ||
2b | 2h | ||||
3 | 61 | 9 | 65 | ||
2c | 2i | ||||
4 | 51 | 10 | 0 | ||
2d | 2j | ||||
5 | 56 | 11 | 0 | ||
2e | 2k | ||||
6 | 86 | ||||
2f |
Table 4 Substrates scope for the productsa
Entry | Product | Yieldb(%) | Entry | Product | Yieldb(%) |
---|---|---|---|---|---|
1 | 78 | 7 | 85 | ||
2a | 2g | ||||
2 | 47 | 8 | 81 | ||
2b | 2h | ||||
3 | 61 | 9 | 65 | ||
2c | 2i | ||||
4 | 51 | 10 | 0 | ||
2d | 2j | ||||
5 | 56 | 11 | 0 | ||
2e | 2k | ||||
6 | 86 | ||||
2f |
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