First Metal-Free Synthesis of Tetracyclic Pyrido and Pyrazino Thienopyrimidinone Molecules
Abstract
1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General Methods
3.2. General Methods
4. Conclusions
Supplementary Materials
Author Contributions
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of all compounds are available from the authors. |
Entry | [Cat] (mol %) | Solvent | Ligand (mol %) | T (°C) | Base 2.62 equiv | Yield (%) [a] |
---|---|---|---|---|---|---|
1 | Pd(OAc)2 (3) | Dioxane | Xantphos (4) | 120 | Cs2CO3 | 67 |
2 | Pd(OAc)2 (3) | Dioxane | PPh3 (6) | 120 | Cs2CO3 | 33 |
3 | Pd(OAc)2 (5) | Dioxane | 10-phenanthroline (10) | 120 | Cs2CO3 | 18 |
4 | Pd(OAc)2 (3) | Dioxane | - | 120 | Cs2CO3 | 14 |
5 | Pd(OAc)2 (3) | Toluene | - | 120 | Cs2CO3 | [b] |
6 | Pd(OAc)2 (3) | Toluene | PPh3 (6) | 120 | Cs2CO3 | 8 |
7 | Pd(OAc)2 (3) | Toluene | PPh3 (6) | 150 | Cs2CO3 | 10 |
8 | Pd(OAc)2 (3) | Toluene/EtOH (2:1) | - | 120 | Cs2CO3 | - |
9 | Pd(OAc)2 (3) | Toluene | - | 150 | Cs2CO3 | 41 |
10 | Pd(OAc)2 (3) | Toluene | - | 150 | K3PO4 | - |
11 | Pd(OAc)2 (3) | DMA | - | 150 | Cs2CO3 | [c] |
12 | Pd(TFA)2 (5) | Toluene | - | 120 | Cs2CO3 | 61 |
13 | Pd(dppf)Cl2·DCM (3) | Toluene | - | 120 | Cs2CO3 | - |
14 | - | Toluene | - | 150 | Cs2CO3 | 98 |
Entry | [Cat] | Base | % [a] |
---|---|---|---|
1 | Pd(dppf)Cl2·DCM | K2CO3 | 85 |
2 | Pd(dppf)Cl2·DCM | Na2CO3 | 57 |
3 | Pd(PPh3)4 | Na2CO3 | [b] |
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Aounzou, M.; Campos, J.F.; Loubidi, M.; Berteina-Raboin, S. First Metal-Free Synthesis of Tetracyclic Pyrido and Pyrazino Thienopyrimidinone Molecules. Molecules 2018, 23, 1159. https://doi.org/10.3390/molecules23051159
Aounzou M, Campos JF, Loubidi M, Berteina-Raboin S. First Metal-Free Synthesis of Tetracyclic Pyrido and Pyrazino Thienopyrimidinone Molecules. Molecules. 2018; 23(5):1159. https://doi.org/10.3390/molecules23051159
Chicago/Turabian StyleAounzou, Mohammed, Joana F. Campos, Mohammed Loubidi, and Sabine Berteina-Raboin. 2018. "First Metal-Free Synthesis of Tetracyclic Pyrido and Pyrazino Thienopyrimidinone Molecules" Molecules 23, no. 5: 1159. https://doi.org/10.3390/molecules23051159
APA StyleAounzou, M., Campos, J. F., Loubidi, M., & Berteina-Raboin, S. (2018). First Metal-Free Synthesis of Tetracyclic Pyrido and Pyrazino Thienopyrimidinone Molecules. Molecules, 23(5), 1159. https://doi.org/10.3390/molecules23051159