Zinc hydroxyapatite - Catalyzed efficient synthesis of 5-substituted 1H-tetrazoles

Synthetic Communications

Volumn 36, Issue 12, 2006, Pages 1809-1814

  Lakshmi Kantam, M ^a   Balasubrahmanyam, V ^a   Shiva Kumar, K B ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

(2 + 3) Cycloaddition; 5 substituted 1H tetrazoles; Heterogeneous catalyst; Zinc hydroxyapatite

Indexed keywords

HYDROXYAPATITE; NITRILE; PENTETRAZOLE DERIVATIVE; SODIUM AZIDE; TETRAZOLE DERIVATIVE; UNCLASSIFIED DRUG; ZINC COMPLEX; ZINC HYDROXYAPATITE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 33646814730     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910600619630     Document Type: Article

References (23)

1. (a) Butler, R. N. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Scriven, E. F. V. (Eds.); Pergamon: Oxford, U.K., 1996; Vol. 4;
2. (b) Singh, H.; Chala, A. S.; Kapoor, V. K.; Paul, D.; Malhotra, R. K. Medicinal chemistry of tetrazoles. Prog. Med. Chem. 1980, 17, 151;
3. (c) Ostrovskii, V. A.; Pevzner, M. S.; Kofmna, T. P.; Sheherbinin, M. B.; Tselinskii, I. V. Energetic 1,2,4-triazoles and tetrazoles synthesis, structure and properties. Targets Heterocycl. Syst. 1999, 3, 467;
4. (d) Hiskey, M.; Chavez, D. E.; Naud, D. L.; Son, S. F.; Berghout, H. L.; Bome, C. A. Progress in high-nitrogen chemistry in explosives, propellants and pyrotechnics. Proc. Int. Pyrotech. Semin. 2000, 27, 3.
5. (a) Wittenberger, S. J. Recent development in tetrazole chemistry. A review. Org. Prep. Proced. Intl. 1994, 26, 499;
6. (b) Dunica, J. V.; Pierce, M. E.; Santella, J. B. III. Three synthetic routes to a sterically hindered tetrazole: A new one-step mild conversion of an amide into a tetrazole. J. Org. Chem. 1991, 56, 2395-2400;
7. (c) Curran, D. P.; Hadida, S.; Kim, S. Y. tris (2-Perflurohexylethyl)tin azide: A new reagent for preparation of 5-substituted tetrazoles from nitriles with purification by fluorous/organic liquid-liquid extraction. Tetrahedron 1999, 55, 8997-9006;
8. (d) Huff, B. E.; Staszak, M. A new method for the preparation of tetrazoles from nitriles using trimethylsilyazide/trimethylaluminum. Tetrahedron Lett. 1993, 34, 8011-8014;
9. (e) Kumar, A.; Narayanan, R.; Shechter, H. Rearrangement reactions of (Hydroxyphenyl)carbenes. J. Org. Chem. 1996, 61, 4462-4465.
10. Koguro, K.; Ora, T.; Mitsui, S.; Orita, P. Novel synthesis of 5-substituted tetrazoles from nitriles. Synthesis 1998, 6, 910-914.
11. (a) Demko, Z. P.; Sharpless, K. B. Preparation of 5-substituted 1H-tetrazoles from nitriles in water. J. Org. Chem. 2001, 66, 7945-7950;
12. (b) Himo, F.; Demko, Z. P.; Noodleman, L.; Sharpless, K. B. Mechanisms of tetrazole formation by addition of azide to nitriles. J. Am. Chem. Soc. 2002, 124, 12210-12216;
13. (c) Himo, F.; Demko, Z. P.; Noodleman, L.; Sharpless, K. B. Why is tetrazole formation by addition of azide to organic nitriles catalyzed by zinc(II) salts? J. Am. Chem. Soc. 2003, 125, 9983-9987.
14. Amantini, D.; Beleggia, R.; Fringuelli, F.; Pizzo, F.; Vaccoro, L. TBAF-catalyzed synthesis of 5-substituted 1H-tetrazoles under solventless conditions. J. Org. Chem. 2004, 69, 2896-2898.
15. Lakshmi Kantam, M.; Shiva Kumar, K. B.; Sridhar, C. Nanocrystalline ZnO as an efficient heterogeneous catalyst for the synthesis of 5-substituted 1H-tetrazoles. Adv. Synth. Catal. 2005, 347, 1212-1214.
16. Elliott, J. C. Structure and Chemistry of the Apatites and Other Calcium Orthophosphates; Elsevier: Amsterdam, 1994; p. 111.
17. (a) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Creation of a monomeric Ru species on the surface of hydroxyapatite as an efficient heterogeneous catalyst for aerobic alcohol oxidation. J. Am. Chem. Soc. 2000, 122, 7144-7145;
18. (b) Mori, K.; Yamaguchi, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Catalysis of a hydroxyapatite-bound Ru complex: Efficient heterogeneous oxidation of primary amines to nitriles in the presence of molecular oxygen. Chem. Commun. 2001, 461-462;
19. (c) Mori, K.; Yamaguchi, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Efficient heterogeneous oxidation of organosilanes to silanols catalysed by a hydroxyapatite-bound Ru complex in the presence of water and molecular oxygen. New J. Chem. 2002, 26, 1536-1538;
20. (d) Mori, K.; Yamaguchi, K.; Hara, T.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Controlled synthesis of hydroxyapatite-supported palladium complexes as highly efficient heterogeneous catalysts. J. Am. Chem. Soc. 2002, 124, 11572-11573.
21. (a) Choudary, B. M.; Sridhar, C.; Kantam, M. L.; Venkanna, G. T.; Sreedhar, B. Design and evolution of copper apatite catalysts for N-orylation of heterocycles with chloro- and fluoroarenes. J. Am. Chem. Soc. 2005, 127, 9948-9949;
22. (b) Choudary, B. M.; Sridhar, C.; Kantam, M. L.; Sreedhar, B. Hydroxyapatite supported copper catalyst for effective three-component coupling. Tetrahedron Lett. 2004, 45, 7319-7321.
23. Mori, K.; Mitani, Y.; Hara, T.; Mizugaki, T.; Ebitani, K.; Kaneda, K. A single-site hydroxyapatite-bound zinc catalyst for highly efficient chemical fixation of carbon dioxide with epoxides. Chem. Commun. 2005, 3331-3333.