MCM-41-SO3H as an effcient reusable nano-ordered heterogeneous catalyst for the synthesis of divers 1- & 5-substituted 1H-tetrazoles

Document Type : Article

Authors

Laboratory of Organic Synthesis and Natural Products, Department of Chemistry, Sharif University of Technology, Tehran, P.O. Box 111559516, Iran.

Abstract

An improved and efficient method for the synthesis of 1- & 5-substituted 1H-tetrazole derivatives has been described in the presence of nano-ordered MCM-41-SO3H as an effective heterogeneous catalyst. This metal-free protocol, [2+3] cycloaddition of sodium azide to various nitriles or ethyl N-phenyl formimidate intermediate under mild reaction conditions, afford a wide range of 1H-tetrazoles in good to excellent yields. The catalyst was reused for five times without significant loss of catalytic activity.

Keywords

Main Subjects


1. Huisgen, R., Sauer, J., Sturm, H.J., and Markgraf J.H. Ring openings of the azoles, II. The formation of 1.3. 4-oxdiazoles in the acylation of 5-substituted tetrazoles" [Ringo_nungen der Azole, II. Die Bildung von 1.3. 4-Oxdiazolen bei der Acylierung 5-substituierter Tetrazole], Chem. Ber., 93, pp. 2106-2124 (1960). 2. Moderhack, D. Ring transformations in tetrazole chemistry", J. Prakt. Chem., 340, pp. 687-709 (1998). 3. Koldobskii, G.I. and Ostrovskii, V.A. Tetrazoles", Russ. Chem. Rev., 63, p. 797 (1994). 4. Wang, X.S., Tang, Y.Z., Huang, X.F., Qu, Z.R., Che, C.M., and Chan, P.W.H. Syntheses, crystal structures, and luminescent properties of three novel zinc coordination polymers with tetrazolyl ligands", Inorg. Chem., 44, pp. 5278-5285 (2005). 5. Roh, J., V_avrov_a, K., and Hrab_alek, A. Synthesis and functionalization of 5-substituted tetrazoles", Eur. J. Org. Chem., 2012(31), pp. 6101-6118 (2012). 6. Sandmann, G., Schneider, C., and Boger, P. A new non-radioactive assay of phytoene desaturase to evaluate bleaching herbicides", Z. Naturforsch. C., 51, pp. 534-538 (1996). 7. Venkateshwarlu, G., Premalatha, A., Rajanna, K., and Saiprakash, P. Cadmium chloride as an e_cient catalyst for neat synthesis of 5-substituted 1 H-tetrazoles", Synth. Commun., 39, pp. 4479-4485 (2009). 8. Zhu, Y., Ren, Y., and Cai, C. One-pot synthesis of 5-substituted 1H-tetrazoles from aryl bromides with potassium hexakis (cyano-C) ferrate (K4[Fe(CN)6]) as Cyanide Source", Helv. Chim. Acta., 92, pp. 171-175 (2009). 9. Agawane, S.M. and Nagarkar, J.M. Synthesis of 5- substituted 1H-tetrazoles using a nano ZnO/Co3O4 catalyst", Catal. Sci. Tech., 2, pp. 1324-1327 (2012). 10. Patil, D.R., Wagh, Y.B., Ingole, P.G., Singh, K., and Dalal, D.S. _-Cyclodextrin-mediated highly e_cient [2+3] cycloaddition reactions for the synthesis of 5- substituted 1H-tetrazoles", New J. Chem., 37, pp. 3261-3266 (2013). 11. Patil, V.S., Nandre, K.P., Borse, A.U., and Bhosale, S.V. InCl3-catalyzed [2+3] cycloaddition reaction: A rapid synthesis of 5-substituted 1H-tetrazole under microwave irradiation", J. Chem., 9, pp. 1145-1152 (2012). 12. Xie, A., Cao, M., Feng, L., and Dong, W. The synthesis of 5-substituted 1H-tetrazoles in molten tetrabutylammonium bromide", J. Chem. Res., 37, pp. 665-667 (2013). 13. Mani, P., Singh, A.K., and Awasthi, S.K. AgNO3 catalyzed synthesis of 5-substituted-1H-tetrazole via [3+2] cycloaddition of nitriles and sodium azide", Tetrahedron Lett., 55, pp. 1879-1882 (2014). 14. Mani, P., Sharma, C., Kumar, S., and Awasthi, S.K. E_cient heterogeneous silver nanoparticles catalyzed one-pot synthesis of 5-substituted 1H-tetrazoles", J. Mol. Catal. A: Chem., 392, 150-156 (2014). 15. Habibi, D. and Nasrollahzadeh, M. Synthesis of arylaminotetrazoles by ZnCl2/AlCl3/silica as an e_- cient heterogeneous catalyst", Monatsh. Chem. Chem. Mon., 143, pp. 925-930 (2012). 16. Kong, D., Liu, Y., Zhang, J., Li, H., Wang, X., and Liu, G. Hierarchically porous AlPO-5-based microspheres as heterogeneous catalysts for the synthesis of 5-substituted 1H-tetrazoles via [3+2] cycloaddition", New J. Chem., 38, pp. 3078-3083 (2014). 17. Dehghani, F., Sardarian, A.R., and Esmaeilpour, M. Salen complex of Cu(II) supported on superparamagnetic Fe3O4@SiO2 nanoparticles: an e_cient and recyclable catalyst for synthesis of 1-and 5-substituted 1H-tetrazoles", J. Organomet. Chem., 743, pp. 87-96 (2013). 18. Prajapti, S.K., Nagarsenkar, A., and Babu, B.N. An e_cient synthesis of 5-substituted 1H-tetrazoles via B(C6F5)3 catalyzed [3+2] cycloaddition of nitriles and sodium azide", Tetrahedron Lett., 55, pp. 3507-3510 (2014). 19. Razavi, N. and Akhlaghinia, B. Cu(II) immobilized on aminated epichlorohydrin activated silica (CAES): as a new, green and e_cient nanocatalyst for preparation of 5-substituted-1H-tetrazoles", RSC Adv., 5, pp. 12372-12381 (2015). 20. Du, Z., Si, C., Li, Y., Wang, Y., and Lu, J. Improved synthesis of 5-substituted 1H-tetrazoles via the [3+2] cycloaddition of nitriles and sodium azide catalyzed by silica sulfuric acid", Inter. J. Mol. Sci., 13, pp. 4696- 4703 (2013). 21. Esmaeilpour, M., Javidi, J., Dodeji, F.N., and Abarghoui, M.M. Facile synthesis of 1-and 5- substituted 1H-tetrazoles catalyzed by recyclable ligand complex of copper(II) supported on superparamagnetic Fe3O4@SiO2 nanoparticles", J. Mol. Catal. A. Chem., 393, pp. 18-29 (2014). 22. Sharghi, H., Ebrahimpourmoghaddam, S., and Doroodmand, M.M. Facile synthesis of 5-substituted- 1H-tetrazoles and 1-substituted-1H-tetrazoles catalyzed by recyclable 40-phenyl-2,20:60,200-terpyridine copper(II) complex immobilized onto activated multiwalled carbon nanotubes", J. Organomet. Chem., 738, pp. 41-48 (2013). 23. Khala_-Nezhad, A., and Mohammadi, S. Highly e_cient synthesis of 1- and 5-substituted 1H-tetrazoles 1472 F. Matloubi Moghaddam et al./Scientia Iranica, Transactions C: Chemistry and ... 26 (2019) 1463{1473 using chitosan derived magnetic ionic liquid as a recyclable biopolymer-supported catalyst", RSC Adv., 3, pp. 4362-4371 (2013). 24. Bahari, S., and Rezaei, A. HClO4-SiO2 as an e_cient and reusable heterogeneous catalyst for the synthesis of 1-substituted tetrazoles", Lett. Org. Chem., 11, pp. 55-58 (2014). 25. Naeimi, H., and Kiani, F. Ultrasound-promoted onepot three component synthesis of tetrazoles catalyzed by zinc sul_de nanoparticles as a recyclable heterogeneous catalyst", Ultrason. Sonochem., 27, pp. 408-415 (2015). 26. Wiedemann, S.H., Bio, M.M., Brown, L.M., Hansen, K.B., and Langille, N.F. Some practical methods for the application of 5-metallo-1-benzyl-1H-tetrazoles in synthesis", Synlett., 23, pp. 2231-2236 (2012). 27. Parveen, M., Ahmad, F., Mohammed, M.A., and Azaz, S. SiO2-H3BO3 promoted solvent-free, green and sustainable synthesis of bioactive 1-substituted- 1H-tetrazole analogues", New J. Chem., 39, pp. 2028- 2041 (2015). 28. Stein, A., Melde, B.J., and Schroden, R.C. Hybrid inorganic-organic mesoporous silicates-nanoscopic reactors coming of age", Adv. Mater., 12, pp. 1403-1419 (2000). 29. Zhao, X.S., Lu, G., and Millar, G.J. Advances in mesoporous molecular sieve MCM-41", Ind. Eng. Chem. Res., 35, pp. 2075-2090 (1996). 30. Zol_gol, M.A. Silica sulfuric acid/NaNO2 as a novel heterogeneous system for production of thionitrites and disul_des under mild conditions", Tetrahedron, 57, pp. 9509-9511 (2001). 31. Salehi, P., Ali, Zol_gol, M., Shirini, F., and Baghbanzadehm, M. Silica sulfuric acid and silica chloride as e_cient reagents for organic reactions", Curr. Org. Chem., 10, pp. 2171-2189 (2006). 32. Mani, P., Singh, A.K., and Awasthi, S.K. AgNO3 catalyzed synthesis of 5-substituted-1H-tetrazole via [3+2] cycloaddition of nitriles and sodium azide", Tetrahedron Lett., 55, pp. 1879-1882 (2014). 33. Nowrouzi, N., Farahi, S., and Irajzadeh, M. 4-(N,Ndimethylamino) pyridinium acetate as a recyclable catalyst for the synthesis of 5-substituted-1H-tetrazoles", Tetrahedron Lett., 56, pp. 739-742 (2015). 34. Kvnnecke, A., Dorre, R., Kleinpeter, E., and Lippmann, E. Substituenten e_ekte auf azido-tetrazologleichgewichte elektronische und sterische e_ekte bei s-triazolo[4,3-c]tetrazolo[1,5-a]pyrimidinen", Tetrahedron, 35, pp. 1957-1963 (1979). 35. Razavi, N., and Akhlaghinia, B. Cu(II) immobilized on aminated epichlorohydrin activated silica (CAES): as a new, green and e_cient nanocatalyst for preparation of 5-substituted-1H-tetrazoles", RSC Adv., 5, pp. 12372-12381 (2015). 36. Aureggi, V., and Sedelmeier, G. 1,3-dipolar cycloaddition: Click chemistry for the synthesis of 5- substituted tetrazoles from organoaluminum azides and nitriles", Angew. Chem. Int. Ed., 46, pp. 8440- 8444 (2007). 37. Ghodsinia, S.S.E. and Akhlaghinia, B. A rapid metal free synthesis of 5-substituted-1H-tetrazoles using cuttlebone as a natural high e_ective and low cost heterogeneous catalyst", RSC Adv., 5, pp. 49849-49860 (2015). 38. Sreedhar, B., Kumar, A.S., and Yada D. CuFe2O4 nanoparticles: a magnetically recoverable and reusable catalyst for the synthesis of 5-substituted 1Htetrazoles", Tetrahedron Lett., 52, pp. 3565-3569 (2011). 39. Jia, F.C., Zhou, Z.W., Xu, C., Cai, Q., Li, D.K., and Wu, A.X. Expeditious synthesis of 2- phenylquinazolin-4-amines via a Fe/Cu relay-catalyzed domino strategy", Org. Lett., 17, pp. 4236-4239 (2015). 40. Yao, Y.W., Zhou, Y., Lin, B.P., and Yao, C. Click chemistry for the synthesis of 5-substituted 1Htetrazoles from boron-azides and nitriles", Tetrahedron Lett., 54, pp. 6779-6781 (2013). 41. Aridoss, G. and Laali, K.K. Building heterocyclic systems with RC(OR)2+ carbocations in recyclable br_nsted acidic ionic liquids: Facile synthesis of 1-substituted 1H-1,2,3,4-tetrazoles, benzazoles and other ring systems with CH(OEt)3 and EtC(OEt)3 in [EtNH3][NO3] and [PMIM(SO3H)][OTf]", Eur. J. Org. Chem., 2011(15), pp. 2827-2835 (2011). 42. Habibi, D., Nasrollahzadeh, M., and Kamali, T.A. Green synthesis of the 1-substituted 1H-1,2,3,4- tetrazoles by application of the natrolite zeolite as a new and reusable heterogeneous catalyst", Green Chem., 13, pp. 3499-3504 (2011). 43. Dighe, S.N., Jain, K.S., and Srinivasan, K.V. A novel synthesis of 1-aryl tetrazoles promoted by employing the synergy of the combined use of DMSO and an ionic liquid as the solvent system at ambient temperature", Tetrahedron Lett., 50, pp. 6139-6142 (2009). 44. Cantillo, D., Gutmann, B., and Kappe, C.O. Mechanistic insights on azide-nitrile cycloadditions: On the dialkyltin oxide-trimethylsilyl azide route and a new vilsmeier-Haack-type organocatalyst", J. Am. Chem. Soc., 133, pp. 4465-4475 (2011). 45. Sreedhar, B., Kumar, A.S., and Yada, D. CuFe2O4 nanoparticles: a magnetically recoverable and reusable catalyst for the synthesis of 5-substituted 1Htetrazoles", Tetrahedron Lett., 52, pp. 3565-3569 (2011). 46. Rama, V., Kanagaraj, K., and Pitchumani, K. Syntheses of 5-substituted 1H-tetrazoles catalyzed by reusable CoY zeolite", J. Org. Chem., 76, pp. 9090- 9095 (2011). 47. Karimi-Zarchi, M.A. and Nazem, F. Cross-linked poly (4-vinylpyridine) supported azide ion as a versatile and recyclable polymeric reagent for synthesis of 1- substituted-1H-1,2,3,4-tetrazoles", JICS., 11, pp. 91- 99 (2014). F. Matloubi Moghaddam et al./Scientia Iranica, Transactions C: Chemistry and ... 26 (2019) 1463{1473 1473 48. Lang, L., Zhou, H., Xue, M., Wang, X., and Xu, Z. Mesoporous ZnS hollow spheres-catalyzed synthesis of 5-substituted 1H-tetrazoles", Mater. Lett., 106, pp. 443-446 (2013). 49. Lakshmi, K.M., Balasubrahmanyam, V., and Kumar, K.S. Zinc hydroxyapatite-catalyzed e_cient synthesis of 5-substituted 1H-tetrazoles", Synth. Commun., 36, pp. 1809-1814 (2006). 50. Ghodsinia, S.S. and Akhlaghinia, B. A rapid metal free synthesis of 5-substituted-1H-tetrazoles using cuttlebone as a natural high e_ective and low cost heterogeneous catalyst", RSC Adv., 5, pp. 49849-49860 (2015). 51. Rahman, M., Roy, A., Ghosh, M., Mitra, S., Majee, A., and Hajra, A. Organocatalysis by an aprotic imidazolium zwitterion: a dramatic anion-cation cooperative e_ect on azide-nitrile cycloaddition", RSC Adv., 4, pp. 6116-6119 (2014).