Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (4): 1537-1549.DOI: 10.6023/cjoc202210003 Previous Articles Next Articles
ARTICLES
收稿日期:
2022-10-05
修回日期:
2022-11-01
发布日期:
2022-11-21
通讯作者:
南江
基金资助:
Nan Jiang(), Guanjie Huang, Yan Hu, Bo Wang
Received:
2022-10-05
Revised:
2022-11-01
Published:
2022-11-21
Contact:
Nan Jiang
Supported by:
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Nan Jiang, Guanjie Huang, Yan Hu, Bo Wang. Ruthenium-Catalyzed C—H [4+2] Annulation of Quinazolinones with Vinylene Carbonate[J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1537-1549.
Entry | Catalyst | Additive | Temp./℃ | Solvent | Yieldb/% of 3a | Yieldc/% of 4a |
---|---|---|---|---|---|---|
1 | Cp*Rh(MeCN)3(SbF6)2 | 100 | 1,4-Dioxane | 32 | T race | |
2 | [Ru(p-cymene)Cl2]2 | AgSbF6 | 100 | 1,4-Dioxane | 35 | Trace |
3 | [Cp*Co(CO)I2]2 | AgSbF6 | 100 | 1,4-Dioxane | 17 | Trace |
4 | [Cp*IrCl2]2 | AgSbF6 | 100 | 1,4-Dioxane | 24 | Trace |
5 | [Ru(p-cymene)Cl2]2 | 100 | 1,4-Dioxane | 12 | Trace | |
6 | AgSbF6 | 100 | 1,4-Dioxane | Trace | Trace | |
7 | [Ru(p-cymene)Cl2]2 | AgSbF6 | 100 | iPrOH | Trace | Trace |
8 | [Ru(p-cymene)Cl2]2 | AgSbF6 | 100 | Toluene | Trace | Trace |
9 | [Ru(p-cymene)Cl2]2 | AgSbF6 | 100 | DMF | 21 | Trace |
10 | [Ru(p-cymene)Cl2]2 | AgSbF6 | 100 | DCE | 42 | Trace |
11 | [Ru(p-cymene)Cl2]2 | AgSbF6 | 100 | MeCN | 26 | Trace |
12 | [Ru(p-cymene)Cl2]2 | AgOTf | 100 | DCE | 28 | Trace |
13 | [Ru(p-cymene)Cl2]2 | AgNTf2 | 100 | DCE | 25 | Trace |
14 | [Ru(p-cymene)Cl2]2 | AgOAc | 100 | DCE | Trace | Trace |
15 | [Ru(p-cymene)Cl2]2 | AgSbF6 | 50 | DCE | Trace | 58 |
16 | [Ru(p-cymene)Cl2]2 | AgSbF6 | 60 | DCE | Trace | 82 |
17 | [Ru(p-cymene)Cl2]2 | AgSbF6 | 70 | DCE | Trace | 71 |
18 | [Ru(p-cymene)Cl2]2 | AgSbF6 | 80 | DCE | 15 | 14 |
19 | [Ru(p-cymene)Cl2]2 | AgSbF6 | 120 | DCE | 53 | Trace |
20 | [Ru(p-cymene)Cl2]2 | AgSbF6 | 140 | DCE | 61 | Trace |
21d | [Ru(p-cymene)Cl2]2 | AgSbF6 | 140 | DCE | 75 | Trace |
Entry | Catalyst | Additive | Temp./℃ | Solvent | Yieldb/% of 3a | Yieldc/% of 4a |
---|---|---|---|---|---|---|
1 | Cp*Rh(MeCN)3(SbF6)2 | 100 | 1,4-Dioxane | 32 | T race | |
2 | [Ru(p-cymene)Cl2]2 | AgSbF6 | 100 | 1,4-Dioxane | 35 | Trace |
3 | [Cp*Co(CO)I2]2 | AgSbF6 | 100 | 1,4-Dioxane | 17 | Trace |
4 | [Cp*IrCl2]2 | AgSbF6 | 100 | 1,4-Dioxane | 24 | Trace |
5 | [Ru(p-cymene)Cl2]2 | 100 | 1,4-Dioxane | 12 | Trace | |
6 | AgSbF6 | 100 | 1,4-Dioxane | Trace | Trace | |
7 | [Ru(p-cymene)Cl2]2 | AgSbF6 | 100 | iPrOH | Trace | Trace |
8 | [Ru(p-cymene)Cl2]2 | AgSbF6 | 100 | Toluene | Trace | Trace |
9 | [Ru(p-cymene)Cl2]2 | AgSbF6 | 100 | DMF | 21 | Trace |
10 | [Ru(p-cymene)Cl2]2 | AgSbF6 | 100 | DCE | 42 | Trace |
11 | [Ru(p-cymene)Cl2]2 | AgSbF6 | 100 | MeCN | 26 | Trace |
12 | [Ru(p-cymene)Cl2]2 | AgOTf | 100 | DCE | 28 | Trace |
13 | [Ru(p-cymene)Cl2]2 | AgNTf2 | 100 | DCE | 25 | Trace |
14 | [Ru(p-cymene)Cl2]2 | AgOAc | 100 | DCE | Trace | Trace |
15 | [Ru(p-cymene)Cl2]2 | AgSbF6 | 50 | DCE | Trace | 58 |
16 | [Ru(p-cymene)Cl2]2 | AgSbF6 | 60 | DCE | Trace | 82 |
17 | [Ru(p-cymene)Cl2]2 | AgSbF6 | 70 | DCE | Trace | 71 |
18 | [Ru(p-cymene)Cl2]2 | AgSbF6 | 80 | DCE | 15 | 14 |
19 | [Ru(p-cymene)Cl2]2 | AgSbF6 | 120 | DCE | 53 | Trace |
20 | [Ru(p-cymene)Cl2]2 | AgSbF6 | 140 | DCE | 61 | Trace |
21d | [Ru(p-cymene)Cl2]2 | AgSbF6 | 140 | DCE | 75 | Trace |
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