Phosphomolybdic acid (H 3Mo 12O 40P) as a reusable heterogeneous catalyst for the synthesis of 5-substituted 1 H-Tetrazoles via [2+3] cycloaddition of nitriles and sodium azide

Synthetic Communications

Volumn 42, Issue 16, 2012, Pages 2375-2381

  Takale, Santosh ^a   Manave, Smita ^a   Phatangare, Kiran ^a   Padalkar, Vikas ^a   Darvatkar, Nitin ^b   Chaskar, Atul ^a,c  

^a C K Thakur Research Centre   (India)

^b INSTITUTE OF SCIENCE   (India)

^c POLITECNICO DI MILANO   (Italy)

Author keywords

2+3 Cycloaddition; heteropoly acid; nitriles; sodium azide; tetrazoles

Indexed keywords

BENZONITRILE; MOLYBDIC ACID; N,N DIMETHYLFORMAMIDE; SODIUM AZIDE; TETRAZOLE DERIVATIVE;

ARTICLE; CATALYST; CYCLOADDITION; METHODOLOGY; REACTION OPTIMIZATION; SEPARATION TECHNIQUE; SUBSTITUTION REACTION; SYNTHESIS;

EID: 84861490526     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2011.557515     Document Type: Article

References (30)

1. Butler, R. N. In Comprehensive Heterocyclic Chemistry; Pergamon Press: Oxford, UK, 1984; pp. 792-837.
2. 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. (Pubitemid 34310392)
3. Flippin, L. A. Directed metalation and new synthetic transformations of 5-aryltetrazoles. Tetrahedron Lett. 1991, 32, 6857-6860.
4. Wistrand, F. Ek.; Frejd, L. G. T. Synthesis of fused tetrazole-and imidazole derivatives via iodocyclization. Tetrahedron 2003, 59, 6759-6769.
5. 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. (Pubitemid 128494367)
6. Herr, R. J. 5-Substituted-1H-tetrazoles as carboxylic acid isosteres: medicinal chemistry and synthetic methods. Bioorg. Med. Chem. 2002, 10, 3379-3393.
7. Holland, G. F.; Pereira, J. N. Heterocyclic tetrazoles, a new class of lipolysis inhibitors. J. Med. Chem. 1967, 10, 149-154.
8. Figdor, S. K.; Schach von Wittenau, M. Metabolism of 5-(3-pyridyl) tetrazole. J. Med. Chem. 1967, 10, 1158-1159.
9. Kadaba, P. K. Role of protic and dipolar aprotic solvents in heterocyclic syntheses via 1,3-Dipolar cycloaddition reactions. Synthesis 1973, 71-84.
10. 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. (Pubitemid 29314619)
11. 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.
12. 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.
13. Demko, P. Z.; Sharpless, K. B. Preparation of 5-substituted 1H-tetrazoles from nitriles in water. J. Org. Chem. 2001, 66, 7945-7950. (Pubitemid 34182824)
14. 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. (Pubitemid 35154888)
15. 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. (Pubitemid 36994928)
16. Kumar, A.; Narayanan, R.; Shechter, H. Rearrangement reactions of (hydroxyphenyl)-carbenes. J. Org. Chem. 1996, 61, 4462-4465.
17. 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. (Pubitemid 30367364)
18. 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. (Pubitemid 38469057)
19. 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.
20. 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.
21. 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.
22. O as an efficient heterogeneous catalyst for the synthesis of 5-substituted 1H-tetrazoles. Adv. Synth. Catal. 2005, 347, 1212-1214. (Pubitemid 41044809)
23. 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. (Pubitemid 19025278)
24. 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.
25. 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.
26. 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.
27. 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.
28. 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.
29. 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.
30. Gawand, P.; Deokar, H.; Langi, B.; Yadav, A.; Chaskar, A. H3Mo12O40P-catalyzed onepot synthesis of amidoalkyl naphthols. Synth. Commun. 2009, 39, 4171-4179.