Novel one-pot synthesis of 4H-chromene derivatives using amino functionalized silica gel catalyst

Vijaykumar M. Joshi Rupali L. Magar Prashant B. Throat Sunil U. Tekale Bhagavan R. Patil Mangal P. Kale Rajendra P. Pawar

Citation:  Vijaykumar M. Joshi, Rupali L. Magar, Prashant B. Throat, Sunil U. Tekale, Bhagavan R. Patil, Mangal P. Kale, Rajendra P. Pawar. Novel one-pot synthesis of 4H-chromene derivatives using amino functionalized silica gel catalyst[J]. Chinese Chemical Letters, 2014, 25(3): 455-458. doi: 10.1016/j.cclet.2013.12.016 shu

Novel one-pot synthesis of 4H-chromene derivatives using amino functionalized silica gel catalyst

    通讯作者: Rajendra P. Pawar,
摘要: A simple, efficient, and environmentally benign method for the synthesis of 4H-chromene derivatives was developed using well ordered and recoverable amino functionalized silica gel as a base catalyst. The 4H-chromene derivatives were obtained in short time and excellent yield (87%-96%) by three component reaction of aldehydes, malononitrile and cyclic 1,3-diketones in water at 70 ℃.

English

  • 
    1. [1] G.J. Kelly, F. King, F. Kett, Waste elimination in condensation reactions of industrial importance, Green Chem. 4 (2002) 392-399.[1] G.J. Kelly, F. King, F. Kett, Waste elimination in condensation reactions of industrial importance, Green Chem. 4 (2002) 392-399.

    2. [2] J. Weitkamp, M. Hunger, U. Rymsa, Base catalysis on microporous and mesoporous materials: recent progress and perspectives, Microporous Mesoporous Mater. 48 (2001) 255-270.[2] J. Weitkamp, M. Hunger, U. Rymsa, Base catalysis on microporous and mesoporous materials: recent progress and perspectives, Microporous Mesoporous Mater. 48 (2001) 255-270.

    3. [3] R.A. Sheldon, Atom efficiency and catalysis in organic synthesis, Pure Appl. Chem. 72 (2000) 1233-1246.[3] R.A. Sheldon, Atom efficiency and catalysis in organic synthesis, Pure Appl. Chem. 72 (2000) 1233-1246.

    4. [4] A. Zapf, M. Beller, Fine chemical synthesis with homogeneous palladium catalysts: examples, status and trends, Top. Catal. 19 (2002) 101-109.[4] A. Zapf, M. Beller, Fine chemical synthesis with homogeneous palladium catalysts: examples, status and trends, Top. Catal. 19 (2002) 101-109.

    5. [5] B.M. Choudary, M.L. Kantam, P. Sreekanth, et al., Knoevenagel and Aldol condensations catalysed by a new diamino-functionalised mesoporous material, J. Mol. Catal. A 142 (1999) 361-365.[5] B.M. Choudary, M.L. Kantam, P. Sreekanth, et al., Knoevenagel and Aldol condensations catalysed by a new diamino-functionalised mesoporous material, J. Mol. Catal. A 142 (1999) 361-365.

    6. [6] Y. Kubota, Y. Nishizaki, H. Ikeya, et al., Organic silicate hybrid catalysts based on various defined structures for Knoevenagel condensation, Microporous Mesoporous Mater. 70 (2004) 135-149.[6] Y. Kubota, Y. Nishizaki, H. Ikeya, et al., Organic silicate hybrid catalysts based on various defined structures for Knoevenagel condensation, Microporous Mesoporous Mater. 70 (2004) 135-149.

    7. [7] Y. Wan, D. Zhao, On the controllable soft-templating approach to mesoporous silicates, Chem. Rev. 107 (2007) 2821-2860.[7] Y. Wan, D. Zhao, On the controllable soft-templating approach to mesoporous silicates, Chem. Rev. 107 (2007) 2821-2860.

    8. [8] Q.Q. Wang, D.F. Shantz, Ordered mesoporous silica-based inorganic nanocomposites, J. Solid State Chem. 181 (2008) 1659-1669.[8] Q.Q. Wang, D.F. Shantz, Ordered mesoporous silica-based inorganic nanocomposites, J. Solid State Chem. 181 (2008) 1659-1669.

    9. [9] X.G. Wang, K.S.K. Lin, J.C.C. Chan, S.F. Cheng, Direct synthesis and catalytic applications of ordered large pore aminopropyl-functionalized SBA-15 mesoporous materials, J. Phys. Chem. B 109 (2005) 1763-1769.[9] X.G. Wang, K.S.K. Lin, J.C.C. Chan, S.F. Cheng, Direct synthesis and catalytic applications of ordered large pore aminopropyl-functionalized SBA-15 mesoporous materials, J. Phys. Chem. B 109 (2005) 1763-1769.

    10. [10] Y. Kubota, K. Goto, S. Miyata, et al., Enhanced effect of mesoporous silica on basecatalyzed Aldol reaction, Chem. Lett. 32 (2003) 234-235.[10] Y. Kubota, K. Goto, S. Miyata, et al., Enhanced effect of mesoporous silica on basecatalyzed Aldol reaction, Chem. Lett. 32 (2003) 234-235.

    11. [11] A.C. Blanc, D.J. Macquarrie, S. Valle, et al., The preparation and use of novel immobilised guanidine catalysts in base-catalysed epoxidation and condensation reactions, Green Chem. 2 (2000) 283-288.[11] A.C. Blanc, D.J. Macquarrie, S. Valle, et al., The preparation and use of novel immobilised guanidine catalysts in base-catalysed epoxidation and condensation reactions, Green Chem. 2 (2000) 283-288.

    12. [12] X.G. Wang, Y.H. Tseng, J.C.C. Chan, S.F. Cheng, Catalytic applications of aminopropylated mesoporous silica prepared by a template-free route in flavanones, J. Catal. 233 (2005) 266-275.[12] X.G. Wang, Y.H. Tseng, J.C.C. Chan, S.F. Cheng, Catalytic applications of aminopropylated mesoporous silica prepared by a template-free route in flavanones, J. Catal. 233 (2005) 266-275.

    13. [13] M. Luechinger, A. Kienhofer, G.D. Pirngruber, Immobilized complexes of metals with amino acid ligands -a first step toward the development of new biomimetic catalysts, Chem. Mater. 18 (2006) 1330-1336.[13] M. Luechinger, A. Kienhofer, G.D. Pirngruber, Immobilized complexes of metals with amino acid ligands -a first step toward the development of new biomimetic catalysts, Chem. Mater. 18 (2006) 1330-1336.

    14. [14] D. Lu, Y. Li, Y. Gong, Organocatalytic asymmetric tandem Michael additionhemiacetalization: a route to chiral dihydrocoumarins, chromanes, and 4Hchromenes, J. Org. Chem. 75 (2010) 6900-6907.[14] D. Lu, Y. Li, Y. Gong, Organocatalytic asymmetric tandem Michael additionhemiacetalization: a route to chiral dihydrocoumarins, chromanes, and 4Hchromenes, J. Org. Chem. 75 (2010) 6900-6907.

    15. [15] W. Kemnitzer, J. Drewe, S. Jiang, et al., Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell and caspase-based high throughput screening assay. 4. Structure-activity relationships of N-alkyl substituted pyrrole fused at the 7,8-positions, J. Med. Chem. 51 (2008) 417-423.[15] W. Kemnitzer, J. Drewe, S. Jiang, et al., Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell and caspase-based high throughput screening assay. 4. Structure-activity relationships of N-alkyl substituted pyrrole fused at the 7,8-positions, J. Med. Chem. 51 (2008) 417-423.

    16. [16] E.C. Witte, P. Neubert, A. Roesch, 7-(Piperazinyl propoxy)-2H-1-benzopyran-2-ones, Ger. Offen DE, 3427985, Chem. Abstr. 104 (1986) 224915f.[16] E.C. Witte, P. Neubert, A. Roesch, 7-(Piperazinyl propoxy)-2H-1-benzopyran-2-ones, Ger. Offen DE, 3427985, Chem. Abstr. 104 (1986) 224915f.

    17. [17] J. Kuthan, Pyrans, thiopyrans, and selenopyrans, Adv. Heterocycl. Chem. 34 (1983) 145-157.[17] J. Kuthan, Pyrans, thiopyrans, and selenopyrans, Adv. Heterocycl. Chem. 34 (1983) 145-157.

    18. [18] M. Suarez, E. Salfran, Y. Verdecia, et al., X-ray and theoretical structural study of novel 5,6,7,8-tetrahydrobenzo-4H-pyrans, Tetrahedron 58 (2002) 953-960.[18] M. Suarez, E. Salfran, Y. Verdecia, et al., X-ray and theoretical structural study of novel 5,6,7,8-tetrahydrobenzo-4H-pyrans, Tetrahedron 58 (2002) 953-960.

    19. [19] A. Molla, E. Hossain, S. Hussain, Multicomponent domino reactions: borax catalyzed synthesis of highly functionalised pyran-annulated heterocycles, RSC Adv. 3 (2013) 21517-21523.[19] A. Molla, E. Hossain, S. Hussain, Multicomponent domino reactions: borax catalyzed synthesis of highly functionalised pyran-annulated heterocycles, RSC Adv. 3 (2013) 21517-21523.

    20. [20] K. Niknam, A. Jamali, Silica-bonded N-propylpiperazine sodium n-propionate as recyclable basic catalyst for synthesis of 3,4-dihydropyrano[c]chromene derivatives and biscoumarins, Chin. J. Catal. 33 (2012) 1840-1849.[20] K. Niknam, A. Jamali, Silica-bonded N-propylpiperazine sodium n-propionate as recyclable basic catalyst for synthesis of 3,4-dihydropyrano[c]chromene derivatives and biscoumarins, Chin. J. Catal. 33 (2012) 1840-1849.

    21. [21] S. Paul, P. Bhattacharyya, A.R. Das, One-pot synthesis of dihydropyrano[2,3-c]chromenes via a three component coupling of aromatic aldehydes, malononitrile, and 3-hydroxycoumarin catalyzed by nano-structured ZnO in water: a green protocol, Tetrahedron Lett. 52 (2011) 4636-4641.[21] S. Paul, P. Bhattacharyya, A.R. Das, One-pot synthesis of dihydropyrano[2,3-c]chromenes via a three component coupling of aromatic aldehydes, malononitrile, and 3-hydroxycoumarin catalyzed by nano-structured ZnO in water: a green protocol, Tetrahedron Lett. 52 (2011) 4636-4641.

    22. [22] N. Martin, C. Pascual, C. Seoane, J.L. Soto, The use of some activated nitriles in heterocyclic syntheses, Heterocycles 26 (1987) 2811-2816.[22] N. Martin, C. Pascual, C. Seoane, J.L. Soto, The use of some activated nitriles in heterocyclic syntheses, Heterocycles 26 (1987) 2811-2816.

    23. [23] A.F. Harb, A.M. Hesien, S.A. Metwally, M.H. Elnagdi, The reaction of ethyl 6-amino-5-cyano-4-aryl-2-methyl-4H-pyran-3-carboxylate with nucleophilic reagents, Ann. Chem. (1989) 585-590.[23] A.F. Harb, A.M. Hesien, S.A. Metwally, M.H. Elnagdi, The reaction of ethyl 6-amino-5-cyano-4-aryl-2-methyl-4H-pyran-3-carboxylate with nucleophilic reagents, Ann. Chem. (1989) 585-590.

    24. [24] S.E. Zayed, E.I. Abou-Elmaged, S.A. Metwally, M.H. Elnagdi, Reactions of sixmembered heterocyclic β-enaminonitriles with electrophilic reagents, Chem. Commun. 56 (1991) 2175-2182.[24] S.E. Zayed, E.I. Abou-Elmaged, S.A. Metwally, M.H. Elnagdi, Reactions of sixmembered heterocyclic β-enaminonitriles with electrophilic reagents, Chem. Commun. 56 (1991) 2175-2182.

    25. [25] 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.[25] 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.

    26. [26] X.S. Wang, D.Q. Shi, S.J. Tu, C.S. Yao, A convenient synthesis of 5-oxo-5,6,7,8-tetrahydro-4H-benzo-[b]-pyran derivatives catalyzed by KF-alumina, Syn. Commun. 33 (2003) 119-126.[26] X.S. Wang, D.Q. Shi, S.J. Tu, C.S. Yao, A convenient synthesis of 5-oxo-5,6,7,8-tetrahydro-4H-benzo-[b]-pyran derivatives catalyzed by KF-alumina, Syn. Commun. 33 (2003) 119-126.

    27. [27] V. Manu, H.M. Mody, H.C. Bajaj, R.V. Jasra, Adsorption of Cu2+ on amino functionalized silica gel with different loading, Ind. Eng. Chem. Res. 48 (2009) 8954-8960.[27] V. Manu, H.M. Mody, H.C. Bajaj, R.V. Jasra, Adsorption of Cu2+ on amino functionalized silica gel with different loading, Ind. Eng. Chem. Res. 48 (2009) 8954-8960.

    28. [28] R.L. Magar, P.B. Thorat, V.B. Jadhav, et al., Silica gel supported polyamine: a versatile catalyst for one pot synthesis of 2-amino-4H-chromene derivatives, J. Mol. Catal. A: Chem. 374-375 (2013) 118-124.[28] R.L. Magar, P.B. Thorat, V.B. Jadhav, et al., Silica gel supported polyamine: a versatile catalyst for one pot synthesis of 2-amino-4H-chromene derivatives, J. Mol. Catal. A: Chem. 374-375 (2013) 118-124.

  • 加载中
计量
  • PDF下载量:  0
  • 文章访问数:  1365
  • HTML全文浏览量:  30
文章相关
  • 发布日期:  2013-12-25
  • 收稿日期:  2013-07-27
  • 网络出版日期:  2013-11-29
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