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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 17
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Original Articles

Amine Salt–Catalyzed Synthesis of 5-Substituted 1H-Tetrazoles from Nitriles

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Pages 2624-2632 | Received 28 Mar 2009, Published online: 05 Aug 2010

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) Valentina , A. ; Gottfried , S. 1,3-Dipolar cycloaddition: Click chemistry for the synthesis of 5-substituted tetrazoles from organoaluminum azides and nitriles. Angew. Chem., Int. Ed. 2007, 46, 8440–8444.
  • (a) Singh , H. ; Chawla , A. S. ; Kapoor , V. K. ; Paul , D. ; Malhotra , R. K. Medicinal chemistry of tetrazoles . Prog. Med. Chem. 1980 , 17 , 151 – 183 ; (b) Juby , P. F. ; Hudyma , T. W. ; Brown , M. Steroids, CCCX: Structure–activity relation of some steroidal hypnotic agents . J. Med. Chem. 1968 , 11 , 111 – 117 .
  • (a) Wang , L. Z. ; Qu , Z. R. ; Zhao , H. ; Wang , X. S. ; Xiong , R. G. ; Xue , Z. L. Isolation and crystallographic characterization of a solid precipitate/intermediate in the preparation of 5-substituted 1H-tetrazoles from nitrile in water . Inorg. Chem. 2003 , 42 , 3969 – 3971 ; (b) Dinca , M. ; Dailly , A. ; Liu , Y. ; Brown , C. M. ; Neumann , D. A. ; Long , J. R. Hydrogen storage in a microporous metal–organic framework with exposed Mn2+ coordination sites . J. Am. Chem. Soc. 2006 , 128 , 16876 – 16883 .
  • (a) Ostrovskii , V. A. ; Pevzner , M. S. ; Kofmna , T. P. ; Shcherbinin , M. B. ; Tselinskii , I. V. Chemistry and properties: Reviews and accounts on heterocyclic chemistry . Targets Heterocycl. Syst. 1999 , 3 , 467 – 526 ; (b) Koldobskii , G. I. ; Ostrovskii , V. A. Tetrazoles . Usp. Khim. 1994 , 63 , 797 – 814 .
  • (a) Curran , D. P. ; Hadida , S. ; Kim , S.-Y. Tris(2-perfluorohexylethyl)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 ; (b) Duncia , J. V. ; Pierce , M. E. ; Santella , 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) Koguro , K. ; Oga , T. ; Mitsui , S. ; Orita , R. Novel synthesis of 5-substituted tetrazoles from nitriles . Synthesis 1998 , 910 – 914 ; (d) Valentina , A. ; Gottfried , S. 1,3-Dipolar cycloaddition: Click chemistry for the synthesis of 5-substituted tetrazoles from organoaluminum azides and nitriles . Angew. Chem., Int. Ed. 2007 , 46 , 8440 – 8444 .
  • (a) Braun , J. ; Keller , W. Synthese von Tetrazol-Verbindungen aus Säurenitrilen . Ber. Dtsch. Chem. Ges. 1932 , 65 , 1677 – 1685 ; (b) Robert , M. H. ; Charles , F. F. Synthesis of iminotetrazoline derivatives as trichomonacidal and fungicidal agents . J. Org. Chem. 1957 , 22 , 1050 – 1053 .
  • (a) Huff , B. E. ; Staszak , M. A. A new method for the preparation of tetrazoles from nitriles using trimethylsilylazide/trimethylaluminum . Tetrahedron. Lett. 1993 , 34 , 8011 – 8014 ; (b) Wittenberger , S. J. ; Donner , B. G. Dialkyltin oxide–mediated addition of trimethylsilyl azide to nitriles: A novel preparation of 5-substituted tetrazols . J. Org. Chem. 1993 , 58 , 4139 – 4141 .
  • (a) Willfia , G. F. ; Ronald , A. H. ; Robert , L. An improved synthesis of 5-substituted tetrazoles . J. Am. Chem. Soc. 1958 , 80 , 3908 – 3911 ; (b) Eugene , L. ; Takashi , E. Synthesis and properties of 5-(substituted) mercaptotetrazoles . J. Org. Chem. 1961 , 26 , 4472 – 4479 ; (c) Mathias , A. ; Anders , H. Fast microwave-assisted preparation of aryl and vinyl nitriles and the corresponding tetrazoles from organo-halides . J. Org. Chem. 2000 , 65 , 7984 – 7989 .
  • (a) Demko , Z. P. ; Sharpless , K. B. An intramolecular [2 + 3] cycloaddition route to fused 5-heterosubstituted tetrazoles. Org. Lett. 2001, 3, 4091–4094; (b) Demko , Z. P. ; Sharpless , K. B. Preparation of 5-substituted 1H-tetrazoles from nitriles in water. J. Org. Chem. 2001, 66, 7945–7950; (c) Demko , Z. P. ; Sharpless , K. B. A click chemistry approach to tetrazoles by Huisgen 1,3-dipolar cycloaddition: Synthesis of 5-sulfonyl tetrazoles from azides and sulfonyl cyanides. Angew. Chem., Int. Ed. 2002, 41, 2110–2113; (d) Demko , Z. P. ; Sharpless , K. B. A click chemistry approach to tetrazoles by Huisgen 1,3-dipolar cycloaddition: Synthesis of 5-acyltetrazoles from azides and acyl cyanides. Angew. Chem., Int. Ed. 2002, 41, 2113–2116; (e) 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.
  • A strip of paper was soaked in a 10 µM iron(III) chloride solution and then dried. In the presence of hydrazoic acid, the color changes from yellow to a bright red. See Feigl , F. Spot Tests in Organic Analysis ; Elsevier : Amsterdam , 1975 .
  • Amantini , D. ; Beleggia , R. ; Fringuelli , F. ; Pizzo , F. ; Vaccaro , L. TBAF-catalyzed synthesis of 5-substituted 1H-tetrazoles under solventless conditions . J. Org. Chem. 2004 , 69 , 2896 – 2898 .
  • (a) Koguro , K. ; Oga , T. ; Mitsui , S. ; Orita , R. Novel synthesis of 5-substituted tetrazoles from nitriles . Synthesis 1998 , 910 – 914 ; (b) Tienan , J. ; Fukuzou , S. K. ; Yoshinori , Y. Copper-catalyzed synthesis of 5-substituted 1H-tetrazoles via the [3 + 2] cycloaddition of nitriles and trimethylsilyl azide . Tetrahedron. Lett. 2008 , 49 , 2824 – 2827 .

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