Functionalized C3-Symmetric Building Blocks—The Chemistry of Triaminotrimesic Acid
Abstract
:1. Introduction
2. Results
2.1. Syntheses of C3-Symmetric Alkyl Triamino-Benzene-Tricarboxylates
2.2. Diazotation and Azide Formation
2.3. Click Reactions
2.4. Alkylation
2.5. Molecular Structures
3. Materials and Methods
3.1. General Procedure for Cyclotrimerizations
3.2. General Procedure for the Syntheses of Azides
3.3. Typical Procedure for the Click Reactions
3.4. Crystal Structure Determination
3.5. NMR Measurements
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References and Notes
- Through this manuscript, we refer to C3-symmetric building blocks: D3-symmetric ones are also included.
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Starting Material | R | Product | Temp. [°C] | Yields [%] |
---|---|---|---|---|
1a | Me | 2a | 130 | 35 a |
1b | Et | 2b | 130 | 28 |
1c | i Pr | 2c | 130 | 18 |
1d | t Bu | 2d | 100 | 15 |
1e | i Bu | 2e | 100 | 12 |
1f | n Pent | 2f | 100 | 22 |
1g | Bn | 2g | 130 | 23 |
Starting Material | R | Product | Yield [%] |
---|---|---|---|
2a | Me | 3a | 60 |
2b | Et | 3b | 47 |
2c | i Pr | 3c | 50 |
2g | Bn | 3g | 36 |
Starting Material | R1 | Product | R2 | Yield |
---|---|---|---|---|
3a | Me | 6a-Ph | Ph | 19 |
3a | Me | 6a-C6H4Br | C6H4Br | 18 |
3b | Et | 6b-Ph | Ph | 27 |
Product | R | Yield [%] |
---|---|---|
7a | Me | 48 |
7b | Et | 38 |
7c | Bn | 51 |
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Schmidt, L.; Wagner, D.; Nieger, M.; Bräse, S. Functionalized C3-Symmetric Building Blocks—The Chemistry of Triaminotrimesic Acid. Molecules 2022, 27, 4369. https://doi.org/10.3390/molecules27144369
Schmidt L, Wagner D, Nieger M, Bräse S. Functionalized C3-Symmetric Building Blocks—The Chemistry of Triaminotrimesic Acid. Molecules. 2022; 27(14):4369. https://doi.org/10.3390/molecules27144369
Chicago/Turabian StyleSchmidt, Lisa, Danny Wagner, Martin Nieger, and Stefan Bräse. 2022. "Functionalized C3-Symmetric Building Blocks—The Chemistry of Triaminotrimesic Acid" Molecules 27, no. 14: 4369. https://doi.org/10.3390/molecules27144369