Phosphomolybdic Acid (H₃Mo₁₂O₄₀P) as a Reusable Heterogeneous Catalyst for the Synthesis of 5-Substituted 1H-Tetrazoles via [2 + 3] Cycloaddition of Nitriles and Sodium Azide

REFERENCES

• Butler , R. N. In Comprehensive Heterocyclic Chemistry ; Pergamon Press : Oxford , UK , 1984 ; pp. 792 – 837 .
   Google Scholar
• Rhonnstad , P. ; Wensbo , D. On the relative strength of the 1H-tetrazol-5-yl- and the 2-(triphenylmethyl)-2H-tetrazol-5-yl-group in directed ortho-lithiation . Tetrahedron Lett. 2002 , 43 , 3137 – 3139 .
   Web of Science ®Google Scholar
• Flippin , L. A. Directed metalation and new synthetic transformations of 5-aryltetrazoles . Tetrahedron Lett. 1991 , 32 , 6857 – 6860 .
   Web of Science ®Google Scholar
• Wistrand , F. Ek. ; Frejd , L. G. T. Synthesis of fused tetrazole- and imidazole derivatives via iodocyclization . Tetrahedron 2003 , 59 , 6759 – 6769 .
   Web of Science ®Google Scholar
• Jursic , B. S. ; LeBlanc , B. W. Preparation of tetrazoles from organic nitriles and sodium azide in micellar media . J. Heterocycl. Chem. 1998 , 35 , 405 – 408 .
   Web of Science ®Google Scholar
• Herr , R. J. 5-Substituted-1H-tetrazoles as carboxylic acid isosteres: medicinal chemistry and synthetic methods . Bioorg. Med. Chem. 2002 , 10 , 3379 – 3393 .
   PubMed Web of Science ®Google Scholar
• Holland , G. F. ; Pereira , J. N. Heterocyclic tetrazoles, a new class of lipolysis inhibitors . J. Med. Chem. 1967 , 10 , 149 – 154 .
   PubMed Web of Science ®Google Scholar
• Figdor , S. K. ; Schach von Wittenau , M. Metabolism of 5-(3-pyridyl)tetrazole . J. Med. Chem. 1967 , 10 , 1158 – 1159 .
   PubMed Web of Science ®Google Scholar
• Kadaba , P. K. Role of protic and dipolar aprotic solvents in heterocyclic syntheses via 1,3-Dipolar cycloaddition reactions . Synthesis 1973 , 71 – 84 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• Modarresi-Alam , A. R. ; Nasrollahzadeh , M. Synthesis of s-arylamino-1H(2H)-tetrazoles and 5-amino-1-aryl-1H-tetrazoles from secondary arylcyanamides in glacial acetic acid: A simple and efficient method . Turk J. Chem. 2009 , 33 , 267 – 280 .
   Web of Science ®Google Scholar
• Demko , P. Z. ; Sharpless , K. B. Preparation of 5-substituted 1H-tetrazoles from nitriles in water . J. Org. Chem. 2001 , 66 , 7945 – 7950 .
   PubMed Web of Science ®Google Scholar
• Himo , F. ; Demko , P. Z. ; Noodleman , L. ; Sharpless , K. B. Mechanisms of tetrazole formation by addition of azide to nitriles. J. Am. Chem. Soc. 2002, 124, 12210–12216.
   PubMed Web of Science ®Google Scholar
• Himo , F. ; Demko , P. Z. ; 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 .
   PubMed Web of Science ®Google Scholar
• Kumar , A. ; Narayanan , R. ; Shechter , H. Rearrangement reactions of (hydroxyphenyl)carbenes . J. Org. Chem. 1996 , 61 , 4462 – 4465 .
   PubMed Web of Science ®Google Scholar
• Gyoung , Y. S. ; Shim , J.-G. ; Yamamoto , Y. Regiospecific synthesis of 2-allylated-5-substituted tetrazoles via palladium-catalyzed reaction of nitriles, trimethylsilyl azide, and allyl acetates . Tetrahedron Lett. 2000 , 41 , 4193 – 4196 .
   Web of Science ®Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar
• Matthews , D. P. ; Green , J. E. ; Shuker , A. J. Parallel synthesis of alkyl tetrazole derivatives using solid support chemistry . J. Comb. Chem. 2000 , 2 , 19 – 23 .
   PubMed Web of Science ®Google Scholar
• Kantam , M. L. ; Shiva Kumar , K. B. ; Phani Raja , K. An efficient synthesis of 5-substituted 1H-tetrazoles using Zn/Al hydrotalcite catalyst . J. Mol. Catal. A: Chem 2006 , 247 , 186 – 188 .
   Web of Science ®Google Scholar
• Jin , T. ; Kitahara , F. ; Kamijo , S. ; Yamamoto , 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 .
   Web of Science ®Google Scholar
• Kantam , M. L. ; 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 .
   Web of Science ®Google Scholar
• Kees , K. L. ; Cheeseman , R. S. ; Prozialeak , D. H. Perfluoro-N-[4-(1H-tetrazol-5-ylmethyl)phenyl]alkanamides. A new class of oral antidiabetic agents . J. Med. Chem. 1989 , 32 , 11 – 13 .
   PubMed Web of Science ®Google Scholar
• Duncia , 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 .
   Web of Science ®Google Scholar
• Sisido , K. ; Nabika , K. ; Isida , T. ; Kozima , S. Formation of organotin—nitrogen bonds III. N-Trialkyltin-5-substituted tetrazoles . J. Organomet. Chem. 1971 , 33 , 337 – 346 .
   Web of Science ®Google Scholar
• Carini , D. J. ; Duncia , J. V. ; Aldrich , P. E. ; Chui , A. T. ; Johnson , A. L. ; Pierce , M. E. ; Price , W. A. ; Santella, III , J. B. ; Wells , G. J. Nonpeptide angiotensin II receptor antagonists: The discovery of a series of N-(biphenylylmethyl)imidazoles as potent, orally active antihypertensives . J. Med. Chem. 1991 , 34 , 2525 – 2547 .
   PubMed Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• Chaskar , A. ; Padalkar , V. ; Phatangare , K. ; Patil , K. ; Langi , B. Heteropoly acids as useful recyclable heterogeneous catalysts for the facile and highly efficient aza-cope rearrangement of N-allylanilines . Appl. Catal. A: Gen. 2009 , 359 , 84 – 87 .
   Web of Science ®Google Scholar
• Phatangare , K. ; Padalkar , V. ; Mhatre , D. ; Patil , K. ; Chaskar , A. Highly efficient and novel method for synthesis of 1,3,5-triarylbenzenes from acetophenones . Synth. Comm. 2009 , 39 , 4117 – 4121 .
   Web of Science ®Google Scholar
• Gawand , P. ; Deokar , H. ; Langi , B. ; Yadav , A. ; Chaskar , A. H3Mo12O40P-catalyzed one-pot synthesis of amidoalkyl naphthols . Synth. Commun. 2009 , 39 , 4171 – 4179 .
   Web of Science ®Google Scholar