Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 24
550
Views
76
CrossRef citations to date
0
Altmetric
Original Articles

Cadmium Chloride as an Efficient Catalyst for Neat Synthesis of 5-Substituted 1H-Tetrazoles

, , &
Pages 4479-4485 | Received 27 Dec 2008, Published online: 12 Nov 2009

REFERENCES

  • (a) Butler , R. N . In Comprehensive Heterocyclic Chemistry ; A. R. Katritzky , C. W. Rees , E. F. V. Scriven (Eds.); Pergamon : Oxford , UK , 1996 ; vol. 4 ; (b) Singh, H.; Chala, A. S.; Kapoor, V. K.; Paul, D.; Malhotra, R. K. Medicinal chemistry of tetrazoles. Prog. Med. Chem. 1980, 17, 151; (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; (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.
  • Huisgen , R. ; Sauer , J. ; Sturm , H. J. ; Markgraf , J. H. Ringoffnungen der azole, II: Die bildung von 1.3.4-oxdiazolen bei der acylierung 5-substituierter Tetrazole . Chem. Ber. 1960 , 93 , 2106 – 2124 .
  • (a) Wittenberger , S. J. Recent development in tetrazole chemistry: A review . Org. Prep. Proced. Intl. 1994 , 26 , 499 ; (b) Dunica , J. V. ; Pierce , M. E. ; Santella , III J. B. 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 ; (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 ; (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 ; (e) Kumar , A. ; Narayanan , R. ; Shechter , H. Rearrangement reactions of (Hydroxyphenyl)carbenes . J. Org. Chem. 1996 , 61 , 4462 – 4465 .
  • Koguro , K. ; Ora , T. ; Mitsui , S. ; Orita , P. Novel synthesis of 5-substituted tetrazoles from nitriles . Synthesis 1998 , 6 , 910 – 914 .
  • (a) Demko , Z. P. ; Sharpless , K. B. Preparation of 5-substituted 1H-tetrazoles from nitriles in water . J. Org. Chem. 2001 , 66 , 7945 – 7950 ; (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 ; (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 .
  • Amantini , D. ; Beleggia , R. ; Fringuelli , F. ; Pizzo , F. ; Vaccoro , L. TBAF-catalyzed synthesis of 5-substituted 1H-tetrazoles under solvent-less conditions . J. Org. Chem. 2004 , 69 , 2896 – 2898 .
  • Su , W. K. ; Hong , Z. ; Shan , W. G. ; Zhang , X. X. A facile synthesis of substituted 1H-1,2,3,4 tetrazoles catalyzed by ytterbium triflate hydrate . Eur. J. Org. Chem. 2006 , 2723 – 2726 .
  • Shie , J. J. ; Fang , J. M. Microwave-assisted one-pot tandem reactions for direct conversion of primary alcohols and aldehydes to triazines and tetrazoles in aqueous media. J. Org. Chem. 2007, 72, 3141–3144.
  • Katritzky , A. R. ; Cai , C. ; Meher , N. K. Efficient synthesis of 1,5-disubstituted tetrazoles . Synthesis 2007 , 1204 – 1208 .
  • Hajra , S. ; Sinha , D. ; Bhowmick , M. Metal triflate–catalyzed reactions of alkenes, NBS, nitriles, and TMSN3: Synthesis of 1,5-disubstituted tetrazoles . J. Org. Chem. 2007 , 72 , 1852 – 1855 .
  • (a) Lakshmi Kantam , M. ; Shiva Kumar , K. B. ; Sridhar , C. Nanocrystalline ZnO as an efficient heterogeneous catalyst for the synthesis of 5-substitued 1H-tetrazoles . Adv. Synth. Catal. 2005 , 347 , 1212 – 1214 ; (b) Lakshmi Kantam , M. ; Balasubramanyam , V. ; Shiva Kumar , K. B. Zinc hydroxyapatite–catalyzed efficient synthesis of 5-substituted 1H-tetrazoles . Syn. Commun. 2006 , 36 , 1809 – 1814 .
  • Keith , J. M. One-step conversion of pyridine N-oxides to tetrazolo [1,5-a]pyridines . J. Org. Chem. 2006 , 71 , 9540 – 9543 .
  • Smoleski , P. ; Mukhopadhyay , S. ; Fátima , M. ; Guedes da Silva , C. ; Adília , M. ; Charmier , J. ; Pombeiro , A. J. L. New water-soluble azido- and derived tetrazolato-platinum(II) complexes with PTA: Easy metal-mediated synthesis and isolation of 5-substituted tetrazoles . Dalton Trans. 2008 , 6546 – 6555 .
  • Vijender , M. ; Kishore , P. ; Satyanarayana , B. Cadmium chloride (CdCl2): An efficient catalyst for conjugate addition of amines to electron-poor alkenes . Synth. Commun. 2007 , 37 , 589 – 592 .
  • Venkat Narsaiah , A. ; Basak , K. ; Nagaiah , K. Cadmium chloride: An efficient catalyst for one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones . Synthesis 2004 , 1253 – 1256 .
  • Ichihara , K. ; Iwasaki , H. ; Ueda , K. ; Takizawa , R. ; Naito , H. ; Tomosugi , M. Synthesis of phosphatidylcholine: An improved method without using the cadmium chloride complex of sn-glycero-3-phosphocholine . Chem. Phys. Lipids. 2005 , 137 , 94 – 99 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.