The DOI matches its Crossref record.
Preparation of 5-Substituted 1 H-Tetrazoles from Nitriles in Water
Abstract
The addition of sodium azide to nitriles to give 1H-tetrazoles is shown to proceed readily in water with zinc salts as catalysts. The scope of the reaction is quite broad; a variety of aromatic nitriles, activated and unactivated alkyl nitriles, substituted vinyl nitriles, thiocyanates, and cyanamides have all been shown to be viable substrates for this reaction.
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Citations
Cited by
Metal Azolate Frameworks: From Crystal Engineering to Functional Materials
Zhang, J.-P., Zhang, Y.-B., Lin, J.-B., & Chen, X.-M. (2012) · Chemical Reviews · doi:10.1021/cr200139g · Cited by 1,733
Chanda, A., & Fokin, V. V. (2009) · Chemical Reviews · doi:10.1021/cr800448q · Cited by 1,534
Butler, R. N., & Coyne, A. G. (2010) · Chemical Reviews · doi:10.1021/cr100162c · Cited by 1,108
Marrying click chemistry with polymerization: expanding the scope of polymeric materials
Golas, P. L., & Matyjaszewski, K. (2010) · Chem. Soc. Rev. · doi:10.1039/b901978m · Cited by 863
Ligand design for functional metal–organic frameworks
Almeida Paz, F. A., Klinowski, J., Vilela, S. M. F., Tomé, J. P. C., Cavaleiro, J. A. S., & Rocha, J. (2012) · Chem. Soc. Rev. · doi:10.1039/c1cs15055c · Cited by 855
Chen, X.-M., & Tong, M.-L. (2007) · Accounts of Chemical Research · doi:10.1021/ar068084p · Cited by 772
‘Click’ Chemistry in Polymer and Material Science: An Update
Binder, W. H., & Sachsenhofer, R. (2008) · Macromolecular Rapid Communications · doi:10.1002/marc.200800089 · Cited by 756
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Xue, D.-X., Cairns, A. J., Belmabkhout, Y., Wojtas, L., Liu, Y., Alkordi, M. H., & Eddaoudi, M. (2013) · Journal of the American Chemical Society · doi:10.1021/ja401429x · Cited by 531
Coumarin heterocyclic derivatives: chemical synthesis and biological activity
Medina, F. G., Marrero, J. G., Macías-Alonso, M., González, M. C., Córdova-Guerrero, I., Teissier García, A. G., & Osegueda-Robles, S. (2015) · Natural Product Reports · doi:10.1039/c4np00162a · Cited by 469
More Sustainable Approaches for the Synthesis of N-Based Heterocycles
Candeias, N. R., Branco, L. C., Gois, P. M. P., Afonso, C. A. M., & Trindade, A. F. (2009) · Chemical Reviews · doi:10.1021/cr800462w · Cited by 403
Noodleman, L., Lovell, T., Han, W.-G., Li, J., & Himo, F. (2004) · Chemical Reviews · doi:10.1021/cr020625a · Cited by 373
An overview of injectable polymeric hydrogels for tissue engineering
Sivashanmugam, A., Arun Kumar, R., Vishnu Priya, M., Nair, S. V., & Jayakumar, R. (2015) · European Polymer Journal · doi:10.1016/j.eurpolymj.2015.05.014 · Cited by 366
Why Is Tetrazole Formation by Addition of Azide to Organic Nitriles Catalyzed by Zinc(II) Salts?
Himo, F., Demko, Z. P., Noodleman, L., & Sharpless, K. B. (2003) · Journal of the American Chemical Society · doi:10.1021/ja030204q · Cited by 353
Self-citationEss, D. H., Jones, G. O., & Houk, K. N. (2006) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.200600431 · Cited by 285
Metadata
- Authors
- Demko, Z. P., & Sharpless, K. B.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2001-11-01
- Volume
- 66
- Issue
- 24
- Pages
- 7945-7950
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W1969872919
- Cited by
- 971
- References
- 0
- FWCI
- 11.50
- Type
- journal article
- Language
- en
- Open access
- closed
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
