Highly Selective Cyclization and Isomerization of Propargylamines to Access Functionalized Quinolines and 1-Azadienes
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General Information
3.2. Experimental Section
3.2.1. Synthesis of Propargylamines following Reported Procedures (J. Org. Chem. 2006, 71, 2064–2070; Org. Lett. 2006, 8, 2405–2408; Tetrahedron 2014, 70, 3134–3140)
3.2.2. General Procedure for the Preparation of Quinolines through Palladium-Catalyzed Cyclization
3.2.3. General Procedure for the Preparation of 1-Azadienes via Bu4NOAc-Promoted Isomerization
3.2.4. General Procedure for the Preparation of Ir-2m
3.2.5. General Procedure for the Preparation of Dihydropyridin-2(1H)-Ones via Cycloaddition Reaction with 1-Azadienes and Homophthalic Anhydride
3.3. Characterization of Products
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Entry | Additive (Catalyst/Base) | Solvent | Yield b |
---|---|---|---|
1 | Pd(dppf)Cl2 | DMF | 20%/0 |
2 | Pd(PPh3)2Cl2 | DMF | 10%/0 |
3 | PdCl2 | DMF | 31%/0 |
4 | Pd(OAc)2 | DMF | 65%/0 |
5 | Pd(TFA)2 | DMF | 45%/0 |
6 | CuCl | DMF | trace/0 |
7 | Cu(OAc)2 | DMF | 15%/0 |
8 | Fe(OTf)3 | DMF | NR/0 |
9 | Ni(acac)2 | DMF | trace/0 |
10 | Pd(OAc)2 | DMSO | 45%/0 |
11 | Pd(OAc)2 | NMP | 60%/0 |
12 | Pd(OAc)2 | DCE | 68%/0 |
13 | Pd(OAc)2 | dioxane | 25%/0 |
14 | Pd(OAc)2 | CH3CN | 58%/0 |
15 | Pd(OAc)2 | toluene | 80%/0 |
16 | Pd(OAc)2/TBAI | toluene | 20%/25% |
17 | Pd(OAc)2/KOAc | toluene | 41%/trace |
18 | Pd(OAc)2/Na2CO3 | toluene | 34%/trace |
19 | Pd(OAc)2/Cs2CO3 | toluene | 15%/30% |
20 | Cs2CO3 | toluene | 0/31% |
21 | Cs2CO3 | DCE | 0/11% |
22 | Cs2CO3 | dioxane | 0/35% |
23 | Cs2CO3 | CH3CN | 0/81% |
24 | Cs2CO3 | DMF | 0/79% |
25 | Na2CO3 | CH3CN | 0/21% |
26 | K2CO3 | CH3CN | 0/50% |
27 | KOAc | CH3CN | 0/40% |
28 | Bu4NOAc | CH3CN | 0/91% |
29 | DABCO | CH3CN | 0/61% |
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Wu, Z.-G.; Zhang, H.; Cao, C.; Lu, C.; Jiang, A.; He, J.; Zhao, Q.; Tang, Y. Highly Selective Cyclization and Isomerization of Propargylamines to Access Functionalized Quinolines and 1-Azadienes. Molecules 2023, 28, 6259. https://doi.org/10.3390/molecules28176259
Wu Z-G, Zhang H, Cao C, Lu C, Jiang A, He J, Zhao Q, Tang Y. Highly Selective Cyclization and Isomerization of Propargylamines to Access Functionalized Quinolines and 1-Azadienes. Molecules. 2023; 28(17):6259. https://doi.org/10.3390/molecules28176259
Chicago/Turabian StyleWu, Zheng-Guang, Hui Zhang, Chenhui Cao, Chaowu Lu, Aiwei Jiang, Jie He, Qin Zhao, and Yanfeng Tang. 2023. "Highly Selective Cyclization and Isomerization of Propargylamines to Access Functionalized Quinolines and 1-Azadienes" Molecules 28, no. 17: 6259. https://doi.org/10.3390/molecules28176259
APA StyleWu, Z. -G., Zhang, H., Cao, C., Lu, C., Jiang, A., He, J., Zhao, Q., & Tang, Y. (2023). Highly Selective Cyclization and Isomerization of Propargylamines to Access Functionalized Quinolines and 1-Azadienes. Molecules, 28(17), 6259. https://doi.org/10.3390/molecules28176259