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An efficient green approach to aldol and cross-aldol condensations of ketones with aromatic aldehydes catalyzed by nanometasilica disulfuric acid in water

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Abstract

Aldol and cross-aldol condensations of aromatic aldehydes with various ketones in the presence of nanometasilica disulfuric acid (NMSDSA) as heterogeneous catalyst are presented. The catalyst was prepared according to the developed earlier method using inexpensive and readily available starting materials. The highly active catalyst gave excellent yields of the desired aldol products without self-condensation reaction taking place. Reaction times were short, the procedure and work-up were simple, and no volatile or hazardous organic solvents were involved. The catalyst could be recovered three times with only slight reduction in activity.

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References

  1. Ogawa, M., Ishili, Y., Nakano, T., and Irifune, S., Chem. Abstr, 1988.

    Google Scholar 

  2. Deli, J., Lorand, T., Szabo, D., and Foldesi, A., Pharmazie, 1984, vol. 39, no. 8, p. 539.

    CAS  Google Scholar 

  3. Leonard, N.J., Miller, L.A., and Berry, J.W., J. Am. Chem. Soc., 1957, vol. 79, no. 6, p. 1482. doi 10.1021/ja01563a056

    Article  CAS  Google Scholar 

  4. Dimmock, J.R., Padmanilayam, M.P., Zello, G.A., Nienaber, K.H., Allen, T.M., Santos, C.L., De Clercq, E., Balzarini, J., Manavathu, E.K., and Stables, J.P., Eur. J. Med. Chem., 2003, vol. 38, no. 2, p. 169. doi 10.1016/S0223-5234(02)01444-7

    Article  CAS  Google Scholar 

  5. Kawamata, J., Inoue, K., Inabe, T., Kiguchi, M., Kato, M., and Taniguchi, Y., Chem. Phys. Lett., 1996, vol. 249, no. 1, p. 29. doi 10.1016/0009-2614(95)01373-3

    Article  CAS  Google Scholar 

  6. Gangadhara and Kishore, K., Polymer, 1995, vol. 36, no. 9, p. 1903. doi 10.1016/0032-3861(95)90938-X

    Article  CAS  Google Scholar 

  7. Robinson, T.P., Ehlers, T., Hubbard, I.V.R.B., Bai, X., Arbiser, J.L., Goldsmith, D.J., and Bowen, J.P., Bioorg. Med. Chem. Lett., 2003, vol. 13, no. 1, p. 115. doi 10.1016/S0960-894X(02)00832-6

    Article  CAS  Google Scholar 

  8. Dinkova-Kostova, A.T., Abeygunawardana, C., and Talalay, P., J. Med. Chem., 1998, vol. 41, no. 26, p. 5287. doi 10.1021/jm980424s

    Article  CAS  Google Scholar 

  9. Piantadosi, C., Hall, I.H., Irvine, J.L., and Carlson, G.L., J. Med. Chem., 1973, vol. 16, no. 7, p. 770.

    Article  CAS  Google Scholar 

  10. Hsieh, C.-T., Hsieh, T.-J., El-Shazly, M., Chuang, D.-W., Tsai, Y.-H., Yen, C.-T., Wu, S.-F., Wu, Y.-C., and Chang, F.-R., Bioorg. Med. Chem. Lett., 2012, vol. 22, no. 12, p. 3912. doi 10.1016/j.bmcl.2012.04.108

    Article  CAS  Google Scholar 

  11. Kumar, H., Devaraji, V., Joshi, R., Jadhao, M., Ahirkar, P., Prasath, R., Bhavana, P., and Ghosh, S. K., RSC Adv., 2015, vol. 5, no. 80, p. 65496. doi 10.1039/C5RA08778C

    Article  CAS  Google Scholar 

  12. Mahapatra, D.K., Asati, V., and Bharti, S.K., Eur. J. Med. Chem., 2015, vol. 92, p. 839. doi 10.1016/j.ejmech.2015.01.051

    Article  CAS  Google Scholar 

  13. Mahapatra, D.K. and Bharti, S.K., Life Sci., 2016, vol. 148, p. 154. doi 10.1016/j.lfs.2016.02.048

    Article  CAS  Google Scholar 

  14. Roussaki, M., Hall, B., Lima, S.C., da Silva, A.C., Wilkinson, S., and Detsi, A., Bioorg. Med. Chem. Lett., 2013, vol. 23, no. 23, p. 6436. doi 10.1016/j.bmcl.2013.09.047

    Article  CAS  Google Scholar 

  15. Thillainayagam, M., Pandian, L., Murugan, K.K., Vijayaparthasarathi, V., Sundaramoorthy, S., Anbarasu, A., and Ramaiah, S., J. Biomol. Struct. Dyn., 2015, vol. 33, no. 5, p. 961. doi 10.1080/07391102.2014.920277

    Article  CAS  Google Scholar 

  16. Ahmed, M.R., Sastry, V.G., Bano, N., Ravichandra, S., and Raghavendra, M., Rasayan J. Chem., 2011, vol. 4, no. 2, p. 289.

    CAS  Google Scholar 

  17. Luo, Y., Song, R., Li, Y., Zhang, S., Liu, Z.-J., Fu, J., and Zhu, H.-L., Bioorg. Med. Chem. Lett., 2012, vol. 22, no. 9, p. 3039. doi 10.1016/j.bmcl.2012.03.080

    Article  CAS  Google Scholar 

  18. Annapurna, A., Mudagal, M.P., Ansari, A., and Rao, A.S., Exp. Clin. Cardiol., 2012, vol. 17, no. 3, p. 110.

    Google Scholar 

  19. Mahapatra, D.K., Bharti, S.K., and Asati, V., Eur. J. Med. Chem., 2015, vol. 98, p. 69. doi 10.1016/j.ejmech.2015.05.004

    Article  CAS  Google Scholar 

  20. Sipos, G. Y., and Sirokman, F., Nature, 1964, vol. 202, no. 4931, p. 489. doi 10.1038/202489a0

    Article  CAS  Google Scholar 

  21. Kozlov, N. G., and Basalaeva, L. I., Russ. J. Gen. Chem., 2004, vol. 74, no. 6, p. 926. doi 10.1023/b:rugc.0000042429.06729.93

    Article  CAS  Google Scholar 

  22. Gall, E. L., Texier-Boullet, F., and Hamelin, J., Synth. Commun., 1999, vol. 29, no. 20, p. 3651. doi 10.1080/00397919908086000

    Article  Google Scholar 

  23. Li, J.-T., Chen, G.-F., Wang, J.-X., and Li, T.-S., Synth. Commun., 1999, vol. 29, no. 6, p. 965. doi 10.1080/00397919908086059

    Article  CAS  Google Scholar 

  24. Sivakumar, P. M., Seenivasan, S. P., Kumar, V., and Doble, M., Bioorg. Med. Chem. Lett., 2007, vol. 17, no. 6, p. 1695. doi 10.1016/j.bmcl.2006.12.112

    Article  CAS  Google Scholar 

  25. Wan, Y., Chen, X.-M., Pang, L.-L., Ma, R., Yue, C.-H., Yuan, R., Lin, W., Yin, W., Bo, R.-C., and Wu, H., Synth. Commun., 2010, vol. 40, no. 15, p. 2320. doi 10.1080/00397910903243781

    Article  CAS  Google Scholar 

  26. Yang, S.-D., Wu, L.-Y., Yan, Z.-Y., Pan, Z.-L., and Liang, Y.-M., J. Mol. Catal. A Chem., 2007, vol. 268, nos. 1–2, p. 107. doi 10.1016/j.molcata.2006.11.039

    Article  CAS  Google Scholar 

  27. Jana, S.K., Catal. Surv. Asia, 2005, vol. 9, no. 1, p. 25. doi 10.1007/s10563-005-3335-y

    Article  CAS  Google Scholar 

  28. Davoodnia, A., Heravi, M. M., Rezaei-Daghigh, L., and Tavakoli-Hoseini, N., Chinese J. Chem., 2010, vol. 28, no. 3, p. 429. doi 10.1002/cjoc.201090091

    Article  CAS  Google Scholar 

  29. Narender, T. and Papi Reddy, K., Tetrahedron Lett., 2007, vol. 48, no. 18, p. 3177. doi 10.1016/j.tetlet.2007.03.054

    Article  CAS  Google Scholar 

  30. Salehi, P., Khodaei, M. M., Zolfigol, M. A., and Keyvan, A., Monatsh. Chem., 2002, vol. 133, no. 10, p. 1291. doi 10.1007/s007060200107

    Article  CAS  Google Scholar 

  31. Rostami, A. and Ahmad-Jangi, F., Chin. Chem. Lett., 2011, vol. 22, no. 9, p. 1029. doi 10.1016/j.cclet.2011.03.015

    Article  CAS  Google Scholar 

  32. Wang, L., Sheng, J., Tian, H., Han, J., Fan, Z., and Qian, C., Synthesis, 2004, vol. 2004, no. 18, p. 3060. doi 10.1055/s-2004-834900

    Article  Google Scholar 

  33. Deng, G. and Ren, T., Synth. Commun., 2003, vol. 33, no. 17, p. 2995. doi 10.1081/SCC-120022473

    Article  CAS  Google Scholar 

  34. Sharma, S.K., Parikh, P. A., and Jasra, R. V., J. Mol. Catal. A Chem., 2007, vol. 278, nos. 1–2, p. 135. doi 10.1016/j.molcata.2007.09.002

    Article  CAS  Google Scholar 

  35. Zhu, Y.-W., Yi, W.-B., and Cai, C., J. Fluor. Chem., 2011, vol. 132, no. 1, p. 71. doi 10.1016/j.jfluchem.2010.11.004

    Article  CAS  Google Scholar 

  36. Zheng, M., Wang, L., Shao, J., and Zhong, Q., Synth. Commun., 1997, vol. 27, no. 2, p. 351. doi 10.1080/00397919708005039

    Article  CAS  Google Scholar 

  37. Nakano, T., Irifune, S., Umano, S., Inada, A., Ishii, Y., and Ogawa, M., J. Org. Chem., 1987, vol. 52, no. 11, p. 2239. doi 10.1021/jo00387a025

    Article  CAS  Google Scholar 

  38. Motiur Rahman, A.F.M., Jeong, B.-S., Kim, D.H., Park, J.K., Lee, E.S., and Jahng, Y., Tetrahedron, 2007, vol. 63, no. 11, p. 2426. doi 10.1016/j.tet.2007.01.020

    Article  Google Scholar 

  39. Hazarkhani, H., Kumar, P., Kondiram, K.S., and Shafi Gadwal, I.M., Synth. Commun., 2010, vol. 40, no. 19, p. 2887. doi 10.1080/00397910903340637

    Article  CAS  Google Scholar 

  40. Lin, P., Li, B., Li, J., Wang, H., Bian, X., and Wang, X., Catal. Lett., 2011, vol. 141, no. 3, p. 459. doi 10.1007/s10562-010-0526-6

    Article  CAS  Google Scholar 

  41. Rawal, K., Mishra, M.K., Dixit, M., and Srinivasarao, M., J. Ind. Eng. Chem., 2012, vol. 18, no. 4, p. 1474. doi 10.1016/j.jiec.2012.02.011

    Article  CAS  Google Scholar 

  42. An, L.-T., Zou, J.-P., and Zhang, L.-L., Catal. Commun., 2008, vol. 9, no. 3, p. 349. doi 10.1016/j.catcom.2007.06.004

    Article  CAS  Google Scholar 

  43. Shrikhande, J.J., Gawande, M.B., and Jayaram, R.V., Catal. Commun., 2008, vol. 9, no. 6, p. 1010. doi 10.1016/j.catcom.2007.10.001

    Article  CAS  Google Scholar 

  44. Yadav, J.S., Reddy, B.V.S., Nagaraju, A., and Sarma, J.A.R.P., Synth. Commun., 2002, vol. 32, no. 6, p. 893. doi 10.1081/SCC-120002700

    Article  CAS  Google Scholar 

  45. Zolfigol, M.A., Tetrahedron, 2001, vol. 57, no. 46, p. 9509. doi 10.1016/S0040-4020(01)00960-7

    Article  CAS  Google Scholar 

  46. Daraei, M., Zolfigol, M.A., Derakhshan-Panah, F., Shiri, M., Kruger, H.G., and Mokhlesi, M., J. Iran. Chem. Soc., 2015, vol. 12, no. 5, p. 855. doi 10.1007/s13738-014-0548-x

    Article  CAS  Google Scholar 

  47. Salehi, P., Ali Zolfigol, M., Shirini, F., and Baghbanzadeh, M., Curr. Org. Chem., 2006, vol. 10, no. 17, p. 2171. doi 10.2174/138527206778742650

    Article  CAS  Google Scholar 

  48. Nakhaei, A., Davoodnia, A., and Morsali, A., Res. Chem. Intermediat., 2015, vol. 41, no. 10, p. 7815. doi 10.1007/s11164-014-1861-9

    Article  CAS  Google Scholar 

  49. Nakhaei, A. and Davoodnia, A., Chinese J. Catal., 2014, vol. 35, no. 10, p. 1761. doi 10.1016/S1872-2067 (14)60174-1

    Article  CAS  Google Scholar 

  50. Davoodnia, A. and Nakhaei, A., Synth. React. Inorg. Metal-Org. Nano-Met. Chem., 2016, vol. 46, no. 7, p. 1073. doi 10.1080/15533174.2015.1004419

    Article  CAS  Google Scholar 

  51. Nakhaei, A., Yadegarian, S., and Davoodnia, A., Heterocycl. Lett., 2016, vol. 6, no. 3, p. 329.

    Google Scholar 

  52. Yadegarian, S., Davoodnia, A., and Nakhaei, A., Orient. J. Chem., 2015, vol. 31, no. 1, p. 573.

    Article  Google Scholar 

  53. Davoodnia, A., Nakhaei, A., and Tavakoli-Hoseini, N., Z. Naturforsch. B, 2016, vol. 71, p. 219.

    Article  CAS  Google Scholar 

  54. Rohaniyan, M., Davoodnia, A., and Nakhaei, A., Appl. Organomet. Chem., 2016, vol. 30, no. 8, p. 626. doi 10.1002/aoc.3479

    Article  CAS  Google Scholar 

  55. Nakhaei, A., Davoodnia, A., and Yadegarian, S., Heterocycl. Lett., 2016, vol. 6, no. 4, p. 601.

    CAS  Google Scholar 

  56. Zolfigol, M.A., Ghaderi, H., Baghery, S., and Mohammadi, L., J. Iran. Chem. Soc., 2017, vol. 14, no. 1, p. 121. doi 10.1007/s13738-016-0964-1

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Young Researchers and Elite Club, Mashhad Branch, Islamic Azad University, Mashhad, Iran

    A. Nakhaei

  2. Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran

    A. Morsali & A. Davoodnia

  3. Research Center for Animal Development Applied Biology, Mashhad Branch, Islamic Azad University, Mashhad, 917568, Iran

    A. Morsali

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  1. A. Nakhaei
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  2. A. Morsali
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  3. A. Davoodnia
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Correspondence to A. Nakhaei.

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Nakhaei, A., Morsali, A. & Davoodnia, A. An efficient green approach to aldol and cross-aldol condensations of ketones with aromatic aldehydes catalyzed by nanometasilica disulfuric acid in water. Russ J Gen Chem 87, 1073–1078 (2017). https://doi.org/10.1134/S1070363217050292

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