Synthesis of Diastereomeric 2,6-bis{[3-(2-Hydroxy-5-substitutedbenzyl)octahydro-1H-benzimidazol-1-yl]methyl}-4-substituted Phenols (R = Me, OMe) by Mannich-Type Tandem Reactions
Abstract
:1. Introduction
2. Results
3. Materials and Methods
3.1. General
3.2. General Procedure: Reaction between Aminal and p-Substituted Phenols
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Tested Solvent System | Solvent Polarity | Temperature/°C | Reaction Time/h | Recovery of Aminal 1/% | Yield for Compounds 4a–b/% |
---|---|---|---|---|---|
Benzene or toluene | Low | 20–40 °C | Up to 40 | >99 | 0 |
1,4-Dioxane | Intermediate | 40 °C | 40 | 65 | <2 |
Ethanol | High | 77 °C | 40 | 0,45 | <2 |
1,4-Dioxane/water | Intermediate–high | 90 °C | 40 | 0,1 | 13–15 |
1,4-Dioxane/water | Intermediate–high | 94–97 °C | 72 | 0 | 22–27 |
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Quiroga, D.; Ríos-Motta, J.; Rivera, A. Synthesis of Diastereomeric 2,6-bis{[3-(2-Hydroxy-5-substitutedbenzyl)octahydro-1H-benzimidazol-1-yl]methyl}-4-substituted Phenols (R = Me, OMe) by Mannich-Type Tandem Reactions. Molbank 2024, 2024, M1876. https://doi.org/10.3390/M1876
Quiroga D, Ríos-Motta J, Rivera A. Synthesis of Diastereomeric 2,6-bis{[3-(2-Hydroxy-5-substitutedbenzyl)octahydro-1H-benzimidazol-1-yl]methyl}-4-substituted Phenols (R = Me, OMe) by Mannich-Type Tandem Reactions. Molbank. 2024; 2024(3):M1876. https://doi.org/10.3390/M1876
Chicago/Turabian StyleQuiroga, Diego, Jaime Ríos-Motta, and Augusto Rivera. 2024. "Synthesis of Diastereomeric 2,6-bis{[3-(2-Hydroxy-5-substitutedbenzyl)octahydro-1H-benzimidazol-1-yl]methyl}-4-substituted Phenols (R = Me, OMe) by Mannich-Type Tandem Reactions" Molbank 2024, no. 3: M1876. https://doi.org/10.3390/M1876