Zinc Hydroxyapatite–Catalyzed Efficient Synthesis of 5‐Substituted 1H‐Tetrazoles

References

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