Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (4): 1226-1239.DOI: 10.6023/cjoc202311001 Previous Articles Next Articles
ARTICLES
李晓勇, 黄丹凤*(), 周玉秀, 刘小康, 王克虎, 王君娇, 胡雨来*()
收稿日期:
2023-11-01
修回日期:
2023-12-11
发布日期:
2023-12-28
基金资助:
Xiaoyong Li, Danfeng Huang(), Yuxiu Zhou, Xiaokang Liu, Kehu Wang, Junjiao Wang, Yulai Hu()
Received:
2023-11-01
Revised:
2023-12-11
Published:
2023-12-28
Contact:
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Xiaoyong Li, Danfeng Huang, Yuxiu Zhou, Xiaokang Liu, Kehu Wang, Junjiao Wang, Yulai Hu. [3+2] Cyclization of Difluoroacetohydrazonoyl Bromides with β-(N,N-Dimethylamino)enones/Enoates/Enamides[J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1226-1239.
Entry | Mole ratio of 1a/2a/base | Base | Solvent | Time/h | Temp./℃ | Isolated yield/% | |
---|---|---|---|---|---|---|---|
1 | 1.0/1.0/1.0 | K2CO3 | THF | 12 | 25 | 70 | |
2 | 1.2/1.0/1.2 | K2CO3 | THF | 12 | 25 | 75 | |
3 | 1.2/1.0/1.5 | K2CO3 | THF | 12 | 25 | 72 | |
4 | 1.5/1.0/1.5 | K2CO3 | THF | 14 | 25 | 84 | |
5 | 1.5/1.0/2.0 | K2CO3 | THF | 14 | 25 | 76 | |
6 | 1.5/1.0/1.5 | K2CO3 | 1,4-Dioxane | 72 | 25 | 60 | |
7 | 1.5/1.0/1.5 | K2CO3 | Toluene | 72 | 25 | 44 | |
8 | 1.5/1.0/1.5 | K2CO3 | DCM | 48 | 25 | 73 | |
9 | 1.5/1.0/1.5 | K2CO3 | DCE | 48 | 25 | 74 | |
10 | 1.5/1.0/1.5 | K2CO3 | EtOH | 72 | 25 | 50 | |
11 | 1.5/1.0/1.5 | K2CO3 | MeCN | 14 | 25 | 72 | |
12 | 1.5/1.0/1.5 | Na2CO3 | THF | 24 | 25 | 69 | |
13 | 1.5/1.0/1.5 | Cs2CO3 | THF | 14 | 25 | 45 | |
14 | 1.5/1.0/1.5 | NaHCO3 | THF | 30 | 25 | 30 | |
15 | 1.5/1.0/1.5 | Et3N | THF | 30 | 25 | 35 | |
16 | 1.5/1.0/1.5 | DBU | THF | 30 | 25 | Trace | |
17 | 1.5/1.0/1.5 | K2CO3 | THF | 20 | 0 | 74 | |
18 | 1.5/1.0/1.5 | K2CO3 | THF | 8 | 40 | 70 |
Entry | Mole ratio of 1a/2a/base | Base | Solvent | Time/h | Temp./℃ | Isolated yield/% | |
---|---|---|---|---|---|---|---|
1 | 1.0/1.0/1.0 | K2CO3 | THF | 12 | 25 | 70 | |
2 | 1.2/1.0/1.2 | K2CO3 | THF | 12 | 25 | 75 | |
3 | 1.2/1.0/1.5 | K2CO3 | THF | 12 | 25 | 72 | |
4 | 1.5/1.0/1.5 | K2CO3 | THF | 14 | 25 | 84 | |
5 | 1.5/1.0/2.0 | K2CO3 | THF | 14 | 25 | 76 | |
6 | 1.5/1.0/1.5 | K2CO3 | 1,4-Dioxane | 72 | 25 | 60 | |
7 | 1.5/1.0/1.5 | K2CO3 | Toluene | 72 | 25 | 44 | |
8 | 1.5/1.0/1.5 | K2CO3 | DCM | 48 | 25 | 73 | |
9 | 1.5/1.0/1.5 | K2CO3 | DCE | 48 | 25 | 74 | |
10 | 1.5/1.0/1.5 | K2CO3 | EtOH | 72 | 25 | 50 | |
11 | 1.5/1.0/1.5 | K2CO3 | MeCN | 14 | 25 | 72 | |
12 | 1.5/1.0/1.5 | Na2CO3 | THF | 24 | 25 | 69 | |
13 | 1.5/1.0/1.5 | Cs2CO3 | THF | 14 | 25 | 45 | |
14 | 1.5/1.0/1.5 | NaHCO3 | THF | 30 | 25 | 30 | |
15 | 1.5/1.0/1.5 | Et3N | THF | 30 | 25 | 35 | |
16 | 1.5/1.0/1.5 | DBU | THF | 30 | 25 | Trace | |
17 | 1.5/1.0/1.5 | K2CO3 | THF | 20 | 0 | 74 | |
18 | 1.5/1.0/1.5 | K2CO3 | THF | 8 | 40 | 70 |
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