An Unexpected Synthesis of 2-Sulfonylquinolines via Deoxygenative C2-Sulfonylation of Quinoline N-Oxides with Sulfonyl Chlorides
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental Section
3.1. General Information
3.2. General Procedure for the Preparation of 2-Sulfonylquinolines 3
3.3. Gram-Scale Synthesis of 3aa
3.4. Characterization Data of Products 3aa–3ta, 3xa and 3ab–3ap
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Entry | R1R2R3N | Solvent | Ratios of 2a to 1a | Yield of 3aa % |
---|---|---|---|---|
1 | Et2NH | THF | 2 | 55 |
2 | Et2NH | DCM | 2 | 67 |
3 | Et2NH | DCE | 2 | 63 |
4 | Et2NH | EtOAc | 2 | 42 |
5 | Et2NH | Acetone | 2 | 0 |
6 | Et2NH | CH3CN | 2 | 47 |
7 | Et2NH | DMF | 2 | 24 |
8 | Me2NH | DCM | 2 | 43 |
9 | IPr2NH | DCM | 2 | 7 |
10 | morpholine | DCM | 2 | 12 |
11 | piperidine | DCM | 2 | 8 |
12 | Et2NH | DCM | 2 | 0 |
13 | Et2NH | DCM | 2.5 | 67 |
14 | Et2NH | DCM | 3 | 66 |
15 | Et2NH | DCM | 1.5 | 53 |
16 b | Et2NH | DCM | 2 | 79 |
17 c | Et2NH | DCM | 2 | 84 |
18 d | Et2NH | DCM | 2 | 82 |
19 e | Et2NH | DCM | 2 | 0 |
20 | none | DCM | 2 | 0 |
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Yang, W.; Tian, Z.-Y.; Lin, Y.-J.; Xie, L.-Y. An Unexpected Synthesis of 2-Sulfonylquinolines via Deoxygenative C2-Sulfonylation of Quinoline N-Oxides with Sulfonyl Chlorides. Molecules 2024, 29, 2863. https://doi.org/10.3390/molecules29122863
Yang W, Tian Z-Y, Lin Y-J, Xie L-Y. An Unexpected Synthesis of 2-Sulfonylquinolines via Deoxygenative C2-Sulfonylation of Quinoline N-Oxides with Sulfonyl Chlorides. Molecules. 2024; 29(12):2863. https://doi.org/10.3390/molecules29122863
Chicago/Turabian StyleYang, Wei, Zhong-Ying Tian, Ying-Jun Lin, and Long-Yong Xie. 2024. "An Unexpected Synthesis of 2-Sulfonylquinolines via Deoxygenative C2-Sulfonylation of Quinoline N-Oxides with Sulfonyl Chlorides" Molecules 29, no. 12: 2863. https://doi.org/10.3390/molecules29122863