One-pot, solvent-free and efficient synthesis of 2,4,6-triarylpyridines catalyzed by nano-titania-supported sulfonic acid as a novel heterogeneous nanocatalyst

Elham Tabrizian Ali Amoozadeh Salman Rahmani Elham Imanifar Saeede Azhari Masoumeh Malmir

Citation:  Elham Tabrizian, Ali Amoozadeh, Salman Rahmani, Elham Imanifar, Saeede Azhari, Masoumeh Malmir. One-pot, solvent-free and efficient synthesis of 2,4,6-triarylpyridines catalyzed by nano-titania-supported sulfonic acid as a novel heterogeneous nanocatalyst[J]. Chinese Chemical Letters, 2015, 26(10): 1278-1282. doi: 10.1016/j.cclet.2015.06.013 shu

One-pot, solvent-free and efficient synthesis of 2,4,6-triarylpyridines catalyzed by nano-titania-supported sulfonic acid as a novel heterogeneous nanocatalyst

    通讯作者: Ali Amoozadeh,
摘要: Nano titania-supported sulfonic acid (n-TSA) has found to be a highly efficient, eco-friendly and recyclable heterogeneous nanocatalyst for the solvent-free synthesis of 2, 4, 6-triarylpyridines through one-pot three-component reaction of acetophenones, aryl aldehydes and ammonium acetate. This reported method illustrates several advantages such as environmental friendliness reaction conditions, simplicity, short reaction time, easy work up, reusability of catalyst and high yields of the products. One new compound is reported too. Furthermore, the catalyst could be recycled after a simple work-up, and reused at least six times without substantial reduction in its catalytic activity.

English

  • 
    1. [1] R.W. Armstrong, A.P. Combs, P.A. Tempest, S.D. Brown, T.A. Keating, Multiplecomponent condensation strategies for combinatorial library synthesis, Acc. Chem. Res. 29(1996) 123-131.[1] R.W. Armstrong, A.P. Combs, P.A. Tempest, S.D. Brown, T.A. Keating, Multiplecomponent condensation strategies for combinatorial library synthesis, Acc. Chem. Res. 29(1996) 123-131.

    2. [2] Y.A. Ibrahim, H. Behbehani, M.R. Ibrahim, Efficient atom economic approaches towards macrocyclic crownamides via ring closure metathesis, Tetrahedron Lett. 43(2002) 4207-4210.[2] Y.A. Ibrahim, H. Behbehani, M.R. Ibrahim, Efficient atom economic approaches towards macrocyclic crownamides via ring closure metathesis, Tetrahedron Lett. 43(2002) 4207-4210.

    3. [3] M. Sathishkumar, S. Nagarajan, P. Shanmugavelan, et al., One-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/scavenger-free conditions, Beilstein J. Org. Chem. 9(2013) 689-697.[3] M. Sathishkumar, S. Nagarajan, P. Shanmugavelan, et al., One-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/scavenger-free conditions, Beilstein J. Org. Chem. 9(2013) 689-697.

    4. [4] R.S. Varma, Solvent-free organic syntheses using supported reagents and microwave irradiation, Green Chem. 1(1999) 43-55.[4] R.S. Varma, Solvent-free organic syntheses using supported reagents and microwave irradiation, Green Chem. 1(1999) 43-55.

    5. [5] H. Naeimi, Z.S. Nazifi, Sulfonated diatomite as heterogeneous acidic nanoporous catalyst for synthesis of 14-aryl-14-H-dibenzo[a,j]xanthenes under green conditions, Appl. Catal. A 477(2014) 132-140.[5] H. Naeimi, Z.S. Nazifi, Sulfonated diatomite as heterogeneous acidic nanoporous catalyst for synthesis of 14-aryl-14-H-dibenzo[a,j]xanthenes under green conditions, Appl. Catal. A 477(2014) 132-140.

    6. [6] P. Sivaguru, A. Lalitha, Ceric ammonium nitrate supported HY-zeolite:an efficient catalyst for the synthesis of 18-dioxo-octahydroxanthenes, Chin. Chem. Lett. 25(2014) 321-323.[6] P. Sivaguru, A. Lalitha, Ceric ammonium nitrate supported HY-zeolite:an efficient catalyst for the synthesis of 18-dioxo-octahydroxanthenes, Chin. Chem. Lett. 25(2014) 321-323.

    7. [7] P. Li, S. Regati, H.C. Huang, et al., A sulfonate-based Cu(I) metal-organic framework as a highly efficient and reusable catalyst for the synthesis of propargylamines under solvent-free conditions, Chin. Chem. Lett. 26(2015) 6-10.[7] P. Li, S. Regati, H.C. Huang, et al., A sulfonate-based Cu(I) metal-organic framework as a highly efficient and reusable catalyst for the synthesis of propargylamines under solvent-free conditions, Chin. Chem. Lett. 26(2015) 6-10.

    8. [8] S.R. Jetti,A. Bhatewara, T. Kadre, S. Jain, Silica-bonded N-propyl sulfamic acid as an efficient recyclable catalyst for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones under heterogeneous conditions, Chin. Chem. Lett. 25(2014) 469-473.[8] S.R. Jetti,A. Bhatewara, T. Kadre, S. Jain, Silica-bonded N-propyl sulfamic acid as an efficient recyclable catalyst for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones under heterogeneous conditions, Chin. Chem. Lett. 25(2014) 469-473.

    9. [9] S. Rahmani, A. Amoozadeh, E. Kolvari, Nano titania-supported sulfonic acid:an efficient and reusable catalyst for a range of organic reactions under solvent free conditions, Catal. Commun. 56(2014) 184-188.[9] S. Rahmani, A. Amoozadeh, E. Kolvari, Nano titania-supported sulfonic acid:an efficient and reusable catalyst for a range of organic reactions under solvent free conditions, Catal. Commun. 56(2014) 184-188.

    10. [10] I.J. Enyedy, S. Sakamuri, W.A. Zaman, K.M. Johnson, S. Wang, Pharmacophorebased discovery of substituted pyridines as novel dopamine transporter inhibitors, Bioorg. Med. Chem. Lett. 13(2003) 513-517.[10] I.J. Enyedy, S. Sakamuri, W.A. Zaman, K.M. Johnson, S. Wang, Pharmacophorebased discovery of substituted pyridines as novel dopamine transporter inhibitors, Bioorg. Med. Chem. Lett. 13(2003) 513-517.

    11. [11] B.Y. Kim, J.B. Ahn, H.W. Lee, et al., Synthesis and biological activity of novel substituted pyridines and purines containing 2,4-thiazolidinedione, Eur. J. Med. Chem. 39(2004) 433-447.[11] B.Y. Kim, J.B. Ahn, H.W. Lee, et al., Synthesis and biological activity of novel substituted pyridines and purines containing 2,4-thiazolidinedione, Eur. J. Med. Chem. 39(2004) 433-447.

    12. [12] E.C. Constable, Metallodendrimers:metal ions as supramolecular glue, Chem. Commun. (1997) 1073-1080.[12] E.C. Constable, Metallodendrimers:metal ions as supramolecular glue, Chem. Commun. (1997) 1073-1080.

    13. [13] E.C. Constable, E.L. Dunphy, C.E. Housecroft, et al., Structural development of free or coordinated 40-(4-pyridyl)-2, 20:60,200-terpyridine ligands through N-alkylation:new strategies for metallamacrocycle formation, Chem. Eur. J. 12(2006) 4600-4610.[13] E.C. Constable, E.L. Dunphy, C.E. Housecroft, et al., Structural development of free or coordinated 40-(4-pyridyl)-2, 20:60,200-terpyridine ligands through N-alkylation:new strategies for metallamacrocycle formation, Chem. Eur. J. 12(2006) 4600-4610.

    14. [14] B.G.G. Lohmeijer, U.S. Schubert, Playing LEGO with macromolecules:design, synthesis, and self-organization with metal complexes, J. Polym. Sci. A:Polym. Chem. 41(2003) 1413-1427.[14] B.G.G. Lohmeijer, U.S. Schubert, Playing LEGO with macromolecules:design, synthesis, and self-organization with metal complexes, J. Polym. Sci. A:Polym. Chem. 41(2003) 1413-1427.

    15. [15] F. Krohnke, The specific synthesis of pyridines and oligopyridines, Synthesis 1(1976) 1-24.[15] F. Krohnke, The specific synthesis of pyridines and oligopyridines, Synthesis 1(1976) 1-24.

    16. [16] G.W.V. Cave, C.L. Raston, Efficient synthesis of pyridines via a sequential solventless aldol condensation and Michael addition, J. Chem. Soc., Perkin Trans. 1(2001) 3258-3264.[16] G.W.V. Cave, C.L. Raston, Efficient synthesis of pyridines via a sequential solventless aldol condensation and Michael addition, J. Chem. Soc., Perkin Trans. 1(2001) 3258-3264.

    17. [17] K.T. Potts, M.J. Cipullo, P. Ralli, G. Theodoridis, Synthesis of 2,6-disubstituted pyridines, polypyridinyls, and annulated pyridines, J. Org. Chem. 47(1982) 3027-3038.[17] K.T. Potts, M.J. Cipullo, P. Ralli, G. Theodoridis, Synthesis of 2,6-disubstituted pyridines, polypyridinyls, and annulated pyridines, J. Org. Chem. 47(1982) 3027-3038.

    18. [18] M. Wang, Z. Yang, Z. Song, Q. Wang, Three-component one-pot synthesis of 2,4,6-triarylpyridines without catalyst and solvent, J. Heterocycl. Chem. 52(2014) 907-910.[18] M. Wang, Z. Yang, Z. Song, Q. Wang, Three-component one-pot synthesis of 2,4,6-triarylpyridines without catalyst and solvent, J. Heterocycl. Chem. 52(2014) 907-910.

    19. [19] A.R. Moosavi-Zare, M.A. Zolfigol, S. Farahmand, et al., Synthesis of 2,4,6-triarylpyridines using ZroCl2 under solvent-free conditions, Synlett 25(2014) 193-196.[19] A.R. Moosavi-Zare, M.A. Zolfigol, S. Farahmand, et al., Synthesis of 2,4,6-triarylpyridines using ZroCl2 under solvent-free conditions, Synlett 25(2014) 193-196.

    20. [20] Z. Zarnegar, J. Safari, M. Borjian-borujeni, Ultrasound-mediated synthesis of 2,4,6-triaryl-pyridines using MgAl2O4 nanostructures, Chem. Heterocycl. Compd. (2015) 1-9.[20] Z. Zarnegar, J. Safari, M. Borjian-borujeni, Ultrasound-mediated synthesis of 2,4,6-triaryl-pyridines using MgAl2O4 nanostructures, Chem. Heterocycl. Compd. (2015) 1-9.

    21. [21] M. Reza, M. Shafiee, R. Moloudi, M. Ghashang, ZnO nanopowder:an efficient catalyst for the preparation of 2,4,6-triaryl pyridines under solvent-free condition, APCBEE Proc. 1(2012) 221-225.[21] M. Reza, M. Shafiee, R. Moloudi, M. Ghashang, ZnO nanopowder:an efficient catalyst for the preparation of 2,4,6-triaryl pyridines under solvent-free condition, APCBEE Proc. 1(2012) 221-225.

    22. [22] J. Safari, S. Gandomi-Ravandi, M. Borujeni, Green and solvent-free procedure for microwave-assisted synthesis of 2,4,6-triarylpyridines catalysed using MgAl2O4 nanocrystals, J. Chem. Sci. 125(2013) 1063-1070.[22] J. Safari, S. Gandomi-Ravandi, M. Borujeni, Green and solvent-free procedure for microwave-assisted synthesis of 2,4,6-triarylpyridines catalysed using MgAl2O4 nanocrystals, J. Chem. Sci. 125(2013) 1063-1070.

    23. [23] A. Amoozadeh, E. Tabrizian, S. Rahmani, Nano titania-supported sulfonic acid catalyzed synthesis of α,α'-bis(substituted-benzylidene)cycloalkanones and their xanthene derivatives under solvent-free conditions, C. R. Chim. 18(2015) 848-857.[23] A. Amoozadeh, E. Tabrizian, S. Rahmani, Nano titania-supported sulfonic acid catalyzed synthesis of α,α'-bis(substituted-benzylidene)cycloalkanones and their xanthene derivatives under solvent-free conditions, C. R. Chim. 18(2015) 848-857.

    24. [24] A. Davoodnia, M. Bakavoli, R. Moloudi, N. Tavakoli-Hoseini, M. Khashi, Highly efficient, one-pot, solvent-free synthesis of 2,4,6-triarylpyridines using a Brønsted-acidic ionic liquid as reusable catalyst, Monatsh. Chem. Chem. Mon. 141(2010) 867-870.[24] A. Davoodnia, M. Bakavoli, R. Moloudi, N. Tavakoli-Hoseini, M. Khashi, Highly efficient, one-pot, solvent-free synthesis of 2,4,6-triarylpyridines using a Brønsted-acidic ionic liquid as reusable catalyst, Monatsh. Chem. Chem. Mon. 141(2010) 867-870.

    25. [25] K.S. Vellayan Kannan, Montmorillonite K10 clay catalyzed one pot synthesis of 2,4,6-trisubstituted pyridine under solvent free condition, Mod. Res. Catal. 2(2013) 42-46.[25] K.S. Vellayan Kannan, Montmorillonite K10 clay catalyzed one pot synthesis of 2,4,6-trisubstituted pyridine under solvent free condition, Mod. Res. Catal. 2(2013) 42-46.

    26. [26] J. Safari, Z. Zarnegar, M. Borujeni, Mesoporous nanocrystalline MgAl2O4:a new heterogeneous catalyst for the synthesis of 2,4,6-triarylpyridines under solventfree conditions, Chem. Pap. 67(2013) 688-695.[26] J. Safari, Z. Zarnegar, M. Borujeni, Mesoporous nanocrystalline MgAl2O4:a new heterogeneous catalyst for the synthesis of 2,4,6-triarylpyridines under solventfree conditions, Chem. Pap. 67(2013) 688-695.

    27. [27] P. Rajput, N.J.P. Subhashini, S. Raj, Synthesis of 2,4,6-triarylpyridines using AlPO4 under solvent-free conditions, J. Sci. Res. 2(2010) 337-342.[27] P. Rajput, N.J.P. Subhashini, S. Raj, Synthesis of 2,4,6-triarylpyridines using AlPO4 under solvent-free conditions, J. Sci. Res. 2(2010) 337-342.

    28. [28] K.S. Reddy, R.B. Reddy, K. Mukkanti, G. Thota, G. Srinivasulu, Synthesis of 2,4,6-triarylpyridines using TBAHS as a catalyst, Rasayan J. Chem. 4(2011) 299-302.[28] K.S. Reddy, R.B. Reddy, K. Mukkanti, G. Thota, G. Srinivasulu, Synthesis of 2,4,6-triarylpyridines using TBAHS as a catalyst, Rasayan J. Chem. 4(2011) 299-302.

  • 加载中
计量
  • PDF下载量:  0
  • 文章访问数:  1038
  • HTML全文浏览量:  2
文章相关
  • 发布日期:  2015-06-17
  • 收稿日期:  2015-02-26
  • 网络出版日期:  2015-06-08
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