Improved Synthesis of 5-Substituted 1H-Tetrazoles via the [3+2] Cycloaddition of Nitriles and Sodium Azide Catalyzed by Silica Sulfuric Acid
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental Section
4. Conclusions
Acknowledgments
References
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Entry | Solvent | Time | mol Ratio of SiO2-H2SO4 | Yield (100%) |
---|---|---|---|---|
1 | Methanol | 12 | 50% | <10 |
2 | Ethanol | 12 | 50% | 10 |
3 | Toulene | 12 | 50% | 5 |
4 | Chloroform | 12 | 50% | No reaction |
5 | DMF | 5 | 50% | 92 |
6 | DMSO | 5 | 50% | 89 |
7 | DMF | 10 | 50% | 85 |
8 | DMF | 5 | 200% | 93 |
Entry | Nitriles | Tetrazoles | Yield (%) |
---|---|---|---|
1 | 88 | ||
2 | 72 | ||
3 | 88 | ||
4 | 79 | ||
5 | 88 | ||
6 | 95 | ||
7 | 92 | ||
8 | 74 | ||
9 | 72 | ||
10 | 88 | ||
11 | 80 | ||
12 | 76 |
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Du, Z.; Si, C.; Li, Y.; Wang, Y.; Lu, J. Improved Synthesis of 5-Substituted 1H-Tetrazoles via the [3+2] Cycloaddition of Nitriles and Sodium Azide Catalyzed by Silica Sulfuric Acid. Int. J. Mol. Sci. 2012, 13, 4696-4703. https://doi.org/10.3390/ijms13044696
Du Z, Si C, Li Y, Wang Y, Lu J. Improved Synthesis of 5-Substituted 1H-Tetrazoles via the [3+2] Cycloaddition of Nitriles and Sodium Azide Catalyzed by Silica Sulfuric Acid. International Journal of Molecular Sciences. 2012; 13(4):4696-4703. https://doi.org/10.3390/ijms13044696
Chicago/Turabian StyleDu, Zhenting, Changmei Si, Youqiang Li, Yin Wang, and Jing Lu. 2012. "Improved Synthesis of 5-Substituted 1H-Tetrazoles via the [3+2] Cycloaddition of Nitriles and Sodium Azide Catalyzed by Silica Sulfuric Acid" International Journal of Molecular Sciences 13, no. 4: 4696-4703. https://doi.org/10.3390/ijms13044696