SnCl2/nano SiO2:A green and reusable heterogeneous catalyst for the synthesis of polyfunctionalized 4H-pyrans

Javad Safaei-Ghomi Raheleh Teymuri Hossein Shahbazi-Alavi Abolfazl Ziarati

Citation:  Javad Safaei-Ghomi, Raheleh Teymuri, Hossein Shahbazi-Alavi, Abolfazl Ziarati. SnCl2/nano SiO2:A green and reusable heterogeneous catalyst for the synthesis of polyfunctionalized 4H-pyrans[J]. Chinese Chemical Letters, 2013, 24(10): 921-925. shu

SnCl2/nano SiO2:A green and reusable heterogeneous catalyst for the synthesis of polyfunctionalized 4H-pyrans

    通讯作者: Javad Safaei-Ghomi,
摘要: A highly efficient and general method for the synthesis of polyfunctionalized 4H-pyrans is established through a one-pot multicomponent cyclocondensation of aromatic aldehydes with CH acids, malononitrile and ethyl acetoacetate using nano silica supported tin (Ⅱ) chloride as a catalyst. In this method SnCl2/nano SiO2 was used as green and reusable catalyst. Excellent yields, short reaction times, simple workup, and inexpensiveness and commercially availability of the catalyst are the advantages of this method.

English

  • 
    1. [1] M.H. Elnagdi, H.A. Elfaham, G.E.H. Elgemeie, Utility of α,β-unsaturated nitrirles in heterocyclic synthesis, Heterocycles 20 (1983) 519-550.[1] M.H. Elnagdi, H.A. Elfaham, G.E.H. Elgemeie, Utility of α,β-unsaturated nitrirles in heterocyclic synthesis, Heterocycles 20 (1983) 519-550.

    2. [2] S. Goldmann, J. Stoltefus, 1,4-Dihydropyridines: effects of chirality and conformation on the calcium antagonist and calcium agonist activities, Angew. Chem. Int. Ed. Engl. 30 (1991) 1559-1578.[2] S. Goldmann, J. Stoltefus, 1,4-Dihydropyridines: effects of chirality and conformation on the calcium antagonist and calcium agonist activities, Angew. Chem. Int. Ed. Engl. 30 (1991) 1559-1578.

    3. [3] L.L. Andreani, E. Lapi, Aspects and orientations of modern pharmacognosy, Boll. Chim. Farm. 99 (1960) 583-586.[3] L.L. Andreani, E. Lapi, Aspects and orientations of modern pharmacognosy, Boll. Chim. Farm. 99 (1960) 583-586.

    4. [4] L. Bonsignore, G. Loy, D. Secci, A. Calignano, Synthesis and pharmacological activity of 2-oxo-(2H) 1-benzopyran-3-carboxamide derivatives, Eur. J. Med. Chem. 28 (1993) 517-520.[4] L. Bonsignore, G. Loy, D. Secci, A. Calignano, Synthesis and pharmacological activity of 2-oxo-(2H) 1-benzopyran-3-carboxamide derivatives, Eur. J. Med. Chem. 28 (1993) 517-520.

    5. [5] G.R. Green, J.M. Evans, A.K. Vong, Pyrans and their benzo derivatives synthesis, in: A.R. Katritsky, C. Rees, E.F.V. Scriven (Eds.), Comprehensive Heterocyclic Chemistry Ⅱ, Pergamon Press, Oxford, 1995, p. 469.[5] G.R. Green, J.M. Evans, A.K. Vong, Pyrans and their benzo derivatives synthesis, in: A.R. Katritsky, C. Rees, E.F.V. Scriven (Eds.), Comprehensive Heterocyclic Chemistry Ⅱ, Pergamon Press, Oxford, 1995, p. 469.

    6. [6] A. Sánchez, F. Hernández, P.C. Cruz, et al., Infrared irradiation-assisted multicomponent synthesis of 2-amino-3-cyano-4H-pyran derivatives, J. Mex. Chem. Soc. 56 (2012) 121-127.[6] A. Sánchez, F. Hernández, P.C. Cruz, et al., Infrared irradiation-assisted multicomponent synthesis of 2-amino-3-cyano-4H-pyran derivatives, J. Mex. Chem. Soc. 56 (2012) 121-127.

    7. [7] K. Urbahns, E. Horvath, J.P. Stasch, F. Mauler, 4-Phenyl-4H-pyrans as IKCa channel blockers, Bioorg. Med. Chem. Lett. 13 (2003) 2637-2639.[7] K. Urbahns, E. Horvath, J.P. Stasch, F. Mauler, 4-Phenyl-4H-pyrans as IKCa channel blockers, Bioorg. Med. Chem. Lett. 13 (2003) 2637-2639.

    8. [8] I. Devi, P.J. Bhuyan, Sodium bromide catalysed one-pot synthesis of tetrahydrobenzo[ b]pyrans via a three-component cyclocondensation under microwave irradiation and solvent free conditions, Tetrahedron Lett. 45 (2004) 8625-8627.[8] I. Devi, P.J. Bhuyan, Sodium bromide catalysed one-pot synthesis of tetrahydrobenzo[ b]pyrans via a three-component cyclocondensation under microwave irradiation and solvent free conditions, Tetrahedron Lett. 45 (2004) 8625-8627.

    9. [9] A. Domling, Recent developments in isocyanide based multicomponent reactions in applied chemistry, Chem. Rev. 106 (2006) 17-89.[9] A. Domling, Recent developments in isocyanide based multicomponent reactions in applied chemistry, Chem. Rev. 106 (2006) 17-89.

    10. [10] D.J. Ramon, M. Yus, Asymmetric multicomponent reactions (AMCRs): the new frontier, Angew. Chem. Int. Ed. 44 (2005) 1602-1634.[10] D.J. Ramon, M. Yus, Asymmetric multicomponent reactions (AMCRs): the new frontier, Angew. Chem. Int. Ed. 44 (2005) 1602-1634.

    11. [11] C. Ma, Y. Yang, Thiazolium-mediated multicomponent reactions: a facile synthesis of 3-aminofuran derivatives, Org. Lett. 7 (2005) 1343-1345.[11] C. Ma, Y. Yang, Thiazolium-mediated multicomponent reactions: a facile synthesis of 3-aminofuran derivatives, Org. Lett. 7 (2005) 1343-1345.

    12. [12] E. Soleimani, M.M. Khodaei, N. Batooie, M. Baghbanzadeh, Water-prompted synthesis of alkyl nitrile derivatives via Knoevenagel condensation and Michael addition reaction, Green Chem. 13 (2011) 566-569.[12] E. Soleimani, M.M. Khodaei, N. Batooie, M. Baghbanzadeh, Water-prompted synthesis of alkyl nitrile derivatives via Knoevenagel condensation and Michael addition reaction, Green Chem. 13 (2011) 566-569.

    13. [13] G. Evano, N. Blanchard, M. Toumi, New copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis, Chem. Rev. 108 (2008) 3054-3131.[13] G. Evano, N. Blanchard, M. Toumi, New copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis, Chem. Rev. 108 (2008) 3054-3131.

    14. [14] N. Martin, C. Pascual, C. Seoane, J.L. Soto, The use of some activated nitriles in heterocyclic syntheses, Heterocycles 26 (1987) 2811-2816.[14] N. Martin, C. Pascual, C. Seoane, J.L. Soto, The use of some activated nitriles in heterocyclic syntheses, Heterocycles 26 (1987) 2811-2816.

    15. [15] S.E. Zayed, E.I. AbouElmaged, S.A. Metwally, M.H. Elnagdi, Reactions of sixmembered heterocyclic b-enaminonitriles with electrophilic reagents, Collect. Czech. Chem. Commun. 56 (1991) 2175-2182.[15] S.E. Zayed, E.I. AbouElmaged, S.A. Metwally, M.H. Elnagdi, Reactions of sixmembered heterocyclic b-enaminonitriles with electrophilic reagents, Collect. Czech. Chem. Commun. 56 (1991) 2175-2182.

    16. [16] D. Kumar, R.V. Buchi, S. Sharad, U. Dube, S. Kapur, A facile one-pot green synthesis and antibacterial activity of 2-amino-4H-pyrans and 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes, Eur. J. Med. Chem. 44 (2009) 3805-3809.[16] D. Kumar, R.V. Buchi, S. Sharad, U. Dube, S. Kapur, A facile one-pot green synthesis and antibacterial activity of 2-amino-4H-pyrans and 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes, Eur. J. Med. Chem. 44 (2009) 3805-3809.

    17. [17] N. SeshuBabu, N. Pasha, K.T. VenkateswaraRao, P.S. Sai Prasad, N. Lingaiah, A heterogeneous strong basic Mg/La mixed oxide catalyst for efficient synthesis of polyfunctionalized pyrans, Tetrahedron Lett. 49 (2008) 2730-2733.[17] N. SeshuBabu, N. Pasha, K.T. VenkateswaraRao, P.S. Sai Prasad, N. Lingaiah, A heterogeneous strong basic Mg/La mixed oxide catalyst for efficient synthesis of polyfunctionalized pyrans, Tetrahedron Lett. 49 (2008) 2730-2733.

    18. [18] D. Fang, J.M. Yang, H.B. Zhang, C.M. Jiao, Synthesis of 4H-pyrans catalyzed by thermol-regulated PEG1000-based ionic liquid/EM, J. Ind. Eng. Chem. 17 (2011) 386-388.[18] D. Fang, J.M. Yang, H.B. Zhang, C.M. Jiao, Synthesis of 4H-pyrans catalyzed by thermol-regulated PEG1000-based ionic liquid/EM, J. Ind. Eng. Chem. 17 (2011) 386-388.

    19. [19] P. Bhattacharyya, K. Pradhan, S. Paul, A.R. Das, Nano crystalline ZnO catalyzed one pot multicomponent reaction for an easy access of fully decorated 4H-pyran scaffolds and its rearrangement to 2-pyridone nucleus in aqueous media, Tetrahedron Lett. 53 (2012) 4687-4691.[19] P. Bhattacharyya, K. Pradhan, S. Paul, A.R. Das, Nano crystalline ZnO catalyzed one pot multicomponent reaction for an easy access of fully decorated 4H-pyran scaffolds and its rearrangement to 2-pyridone nucleus in aqueous media, Tetrahedron Lett. 53 (2012) 4687-4691.

    20. [20] J. Wolinsky, H.S. Haue, Substituted γ-pyrans, J. Org. Chem. 34 (1969) 3169.[20] J. Wolinsky, H.S. Haue, Substituted γ-pyrans, J. Org. Chem. 34 (1969) 3169.

    21. [21] J.C. Wilson, G.S. Mcgrath, S.A. Srinivasan, 4H-pyran charge control agents for electrostatographic toners and developers, US Patent, 6 221 550 (2001).[21] J.C. Wilson, G.S. Mcgrath, S.A. Srinivasan, 4H-pyran charge control agents for electrostatographic toners and developers, US Patent, 6 221 550 (2001).

    22. [22] P. Salehi, M. Dabiri, M.A. Zolfigol, M.A. Bodaghi Fard, Silica sulfuric acid: an efficient and reusable catalyst for the one-pot synthesis of 3, 4-dihydropyrimidin-2(1H)-ones, Tetrahedron Lett. 44 (2003) 2889-2891.[22] P. Salehi, M. Dabiri, M.A. Zolfigol, M.A. Bodaghi Fard, Silica sulfuric acid: an efficient and reusable catalyst for the one-pot synthesis of 3, 4-dihydropyrimidin-2(1H)-ones, Tetrahedron Lett. 44 (2003) 2889-2891.

    23. [23] M. Moghaddas, A. Davoodnia, M. Heravi, N. Tavakoli-Hoseini, Sulfonated carbon catalyzed Biginelli reaction for one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones and-thiones, Chin. J. Catal. 33 (2012) 706-710.[23] M. Moghaddas, A. Davoodnia, M. Heravi, N. Tavakoli-Hoseini, Sulfonated carbon catalyzed Biginelli reaction for one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones and-thiones, Chin. J. Catal. 33 (2012) 706-710.

    24. [24] D.C. Sherrington, A.P. Kybett, Supported Catalysts and Their Applications, The Royal Society of Chemistry, Cambridge, 2001p. 196.[24] D.C. Sherrington, A.P. Kybett, Supported Catalysts and Their Applications, The Royal Society of Chemistry, Cambridge, 2001p. 196.

    25. [25] L. Huang, Z. Wang, T.P. Ang, J. Tan, P.K. Wong, A novel SiO2 supported Pd metal catalyst for the Heck reaction, Catal. Lett. 112 (2006) 219-225.[25] L. Huang, Z. Wang, T.P. Ang, J. Tan, P.K. Wong, A novel SiO2 supported Pd metal catalyst for the Heck reaction, Catal. Lett. 112 (2006) 219-225.

    26. [26] V. Siddaiah, G.M. Basha, R. Srinuvasarao, S.K. Yadav, HClO4-SiO2: an efficient reusable catalyst for the synthesis of 3,4,5-trisubstituted 1,2,4-triazoles under solvent-free conditions, Catal. Lett. 141 (2011) 1511-1520.[26] V. Siddaiah, G.M. Basha, R. Srinuvasarao, S.K. Yadav, HClO4-SiO2: an efficient reusable catalyst for the synthesis of 3,4,5-trisubstituted 1,2,4-triazoles under solvent-free conditions, Catal. Lett. 141 (2011) 1511-1520.

    27. [27] A. Ziarati, J. Safaei-Ghomi, S. Rohani, Pseudo five-component process for the synthesis of functionalized tricarboxamides using CuI nanoparticles as reusable catalyst, Chin. Chem. Lett. 24 (2013) 195-198.[27] A. Ziarati, J. Safaei-Ghomi, S. Rohani, Pseudo five-component process for the synthesis of functionalized tricarboxamides using CuI nanoparticles as reusable catalyst, Chin. Chem. Lett. 24 (2013) 195-198.

    28. [28] J. Safaei-Ghomi, M.A. Ghasemzadeh, Zinc oxide nanoparticles: a highly efficient and readily recyclable catalyst for the synthesis of xanthenes, Chin. Chem. Lett. 23 (2012) 1225-1229.[28] J. Safaei-Ghomi, M.A. Ghasemzadeh, Zinc oxide nanoparticles: a highly efficient and readily recyclable catalyst for the synthesis of xanthenes, Chin. Chem. Lett. 23 (2012) 1225-1229.

    29. [29] A. Ziarati, J. Safaei-Ghomi, S. Rohani, Sonochemically synthesis of pyrazolones using reusable catalyst CuI nanoparticles that was prepared by sonication, Ultrason. Sonochem. 20 (2013) 1069-1075.[29] A. Ziarati, J. Safaei-Ghomi, S. Rohani, Sonochemically synthesis of pyrazolones using reusable catalyst CuI nanoparticles that was prepared by sonication, Ultrason. Sonochem. 20 (2013) 1069-1075.

    30. [30] H.R. Darabi, K. Aghapoor, F. Mohsenzadeh, et al., Heterogeneous SnCl2/SiO2 versus homogeneous SnCl2 acid catalysis in the benzo[N,N]-heterocyclic condensation, Bull. Korean Chem. Soc. 32 (2011) 213-218.[30] H.R. Darabi, K. Aghapoor, F. Mohsenzadeh, et al., Heterogeneous SnCl2/SiO2 versus homogeneous SnCl2 acid catalysis in the benzo[N,N]-heterocyclic condensation, Bull. Korean Chem. Soc. 32 (2011) 213-218.

    31. [31] B.F. Mirjalili, A. Bamoniri, A. Akbari, One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones (thiones) promoted by nano-BF3 SiO2, J. Iran Chem. Soc. 8 (2011) S135-S140.[31] B.F. Mirjalili, A. Bamoniri, A. Akbari, One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones (thiones) promoted by nano-BF3 SiO2, J. Iran Chem. Soc. 8 (2011) S135-S140.

    32. [32] M.M. Heravi, Y.S. Beheshtiha, Z. Pirnia, S. Sadjadi, M. Adibi, One-pot, threecomponent synthesis of 4H-pyrans using Cu(Ⅱ) oxymetasilicate, Synth. Commun. 39 (2009) 3663-3667.[32] M.M. Heravi, Y.S. Beheshtiha, Z. Pirnia, S. Sadjadi, M. Adibi, One-pot, threecomponent synthesis of 4H-pyrans using Cu(Ⅱ) oxymetasilicate, Synth. Commun. 39 (2009) 3663-3667.

    33. [33] U.R. Pratap, D.V. Jawale, P.D. Netankar, R.A. Mane, Baker's yeast catalyzed one-pot three-component synthesis of polyfunctionalized 4H-pyrans, Tetrahedron Lett. 52 (2011) 5817-5819.[33] U.R. Pratap, D.V. Jawale, P.D. Netankar, R.A. Mane, Baker's yeast catalyzed one-pot three-component synthesis of polyfunctionalized 4H-pyrans, Tetrahedron Lett. 52 (2011) 5817-5819.

    34. [34] S. Banerjee, Al Horn, H. Khatri, G. Sereda, A green one-pot multicomponent synthesis of 4H-pyrans and polysubstituted aniline derivatives of biological, pharmacological, and optical applications using silica nanoparticles as reusable catalyst, Tetrahedron Lett. 52 (2011) 1878-1881.[34] S. Banerjee, Al Horn, H. Khatri, G. Sereda, A green one-pot multicomponent synthesis of 4H-pyrans and polysubstituted aniline derivatives of biological, pharmacological, and optical applications using silica nanoparticles as reusable catalyst, Tetrahedron Lett. 52 (2011) 1878-1881.

    35. [35] K. Urbahns, H.G. Heine, B. Junge, et al., Substituted 4H-pyrans with a modulating effect on calcium channels, EP Patents, 0758648 (1997).[35] K. Urbahns, H.G. Heine, B. Junge, et al., Substituted 4H-pyrans with a modulating effect on calcium channels, EP Patents, 0758648 (1997).

  • 加载中
计量
  • PDF下载量:  0
  • 文章访问数:  1899
  • HTML全文浏览量:  45
文章相关
  • 收稿日期:  2013-02-21
  • 网络出版日期:  2013-06-06
通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索

/

返回文章