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Fructose-catalyzed synthesis of tetrahydrobenzo[b]pyran derivatives: Investigation of kinetics and mechanism

Sayyedeh Shadfar Pourpanah ,  Sayyed Mostafa Habibi-Khorassani ,  Mehdi Shahraki

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引用本文: Sayyedeh Shadfar Pourpanah, Sayyed Mostafa Habibi-Khorassani, Mehdi Shahraki. Fructose-catalyzed synthesis of tetrahydrobenzo[b]pyran derivatives: Investigation of kinetics and mechanism[J]. 催化学报, 2015, 36(5): 757-763. doi: 10.1016/S1872-2067(14)60302-8 shu
Citation:  Sayyedeh Shadfar Pourpanah, Sayyed Mostafa Habibi-Khorassani, Mehdi Shahraki. Fructose-catalyzed synthesis of tetrahydrobenzo[b]pyran derivatives: Investigation of kinetics and mechanism[J]. Chinese Journal of Catalysis, 2015, 36(5): 757-763. doi: 10.1016/S1872-2067(14)60302-8 shu

Fructose-catalyzed synthesis of tetrahydrobenzo[b]pyran derivatives: Investigation of kinetics and mechanism

    通讯作者: Sayyed Mostafa Habibi-Khorassani
摘要: Fructose was used as an efficient catalyst for three-component condensation reactions of aryl aldehydes, malononitrile, and dimedone in a mixture of EtOH and H2O as green solvents. The advantages of this method are a short reaction time, high yields, low cost, easy accesses, and simple work-up. The mechanism of the synthesis of a derivative of 4H-tetrahydrobenzo[b]pyran was clarified using spectroscopic kinetic methods. The activation energy (Ea = 65.34 kJ/mol) and related kinetic parameters (ΔG‡ = 69.14 kJ/mol, ΔS‡ = 20.99 J/(mol·K), and ΔH‡ = 62.89 kJ/mol) were calculated, based on the effects of temperature, concentration, and solvent. The first step in the proposed mechanism was identified as the rate-determining step (k1), based on the steady-state approximation.

English

    1. [1] Alvey L, Prado S, Huteau V, Saint-Joanis B, Michel S, Koch M, Cole S T, Tillequin F, Janin Y L. Bioorg Med Chem, 2008, 16: 8264[1] Alvey L, Prado S, Huteau V, Saint-Joanis B, Michel S, Koch M, Cole S T, Tillequin F, Janin Y L. Bioorg Med Chem, 2008, 16: 8264

    2. [2] Symeonidis T, Chamilos M, Hadjipavlou-Litina D J, Kallitsakis M, Litinas K E. Bioorg Med Chem Lett, 2009, 19: 1139[2] Symeonidis T, Chamilos M, Hadjipavlou-Litina D J, Kallitsakis M, Litinas K E. Bioorg Med Chem Lett, 2009, 19: 1139

    3. [3] Narender T, Shweta, Gupta S. Bioorg Med Chem Lett, 2004, 14: 3913[3] Narender T, Shweta, Gupta S. Bioorg Med Chem Lett, 2004, 14: 3913

    4. [4] Lakshmi V, Pandey K, Kapil A, Singh N, Samant M, Dube A. Phytomedicine, 2007, 14: 36[4] Lakshmi V, Pandey K, Kapil A, Singh N, Samant M, Dube A. Phytomedicine, 2007, 14: 36

    5. [5] Kumar D, Reddy V B, Sharad S, Dube U, Kapur S. Eur J Med Chem, 2009, 44: 3805[5] Kumar D, Reddy V B, Sharad S, Dube U, Kapur S. Eur J Med Chem, 2009, 44: 3805

    6. [6] El-Agrody A M, El-Hakim M H, El-Latif M S A, Fakery A H, El-Sayed E S M, El-Ghareab K A. Acta Pharm, 2000, 50: 111[6] El-Agrody A M, El-Hakim M H, El-Latif M S A, Fakery A H, El-Sayed E S M, El-Ghareab K A. Acta Pharm, 2000, 50: 111

    7. [7] Konkoy C S, Fick D B, Cai S X, Lan N C, Keana J F W. Chem Abstr, 2001, 134a: 29313[7] Konkoy C S, Fick D B, Cai S X, Lan N C, Keana J F W. Chem Abstr, 2001, 134a: 29313

    8. [8] Niknam K, Borazjani N, Rashidian R, Jamali A. Chin J Catal (催化学报), 2013, 34: 2245[8] Niknam K, Borazjani N, Rashidian R, Jamali A. Chin J Catal (催化学报), 2013, 34: 2245

    9. [9] Devi I, Bhuyan P J. Tetrahedron Lett, 2004, 45: 8625[9] Devi I, Bhuyan P J. Tetrahedron Lett, 2004, 45: 8625

    10. [10] Tu S J, Jiang H, Zhung Q Y, Miu C B, Shi D Q, Wang X S, Gao Y. Chin J Org Chem, 2003, 23: 488[10] Tu S J, Jiang H, Zhung Q Y, Miu C B, Shi D Q, Wang X S, Gao Y. Chin J Org Chem, 2003, 23: 488

    11. [11] Jin T S, Wang A Q, Shi F, Han L S, Liu L B, Li T S. Arkivoc, 2006: 78[11] Jin T S, Wang A Q, Shi F, Han L S, Liu L B, Li T S. Arkivoc, 2006: 78

    12. [12] Balalaie S, Shiekh-Ahmadi M, Bararjanian M. Catal Commun, 2007, 8: 1724[12] Balalaie S, Shiekh-Ahmadi M, Bararjanian M. Catal Commun, 2007, 8: 1724

    13. [13] Abdolmohammadi S, Balalaie S. Tetrhedron Lett, 2007, 48: 3299[13] Abdolmohammadi S, Balalaie S. Tetrhedron Lett, 2007, 48: 3299

    14. [14] Gao S, Tsai C H, Tseng C, Yao C F. Tetrahedron, 2008, 64: 9143[14] Gao S, Tsai C H, Tseng C, Yao C F. Tetrahedron, 2008, 64: 9143

    15. [15] Seifi M, Sheibani H. Catal Lett, 2008, 126: 275[15] Seifi M, Sheibani H. Catal Lett, 2008, 126: 275

    16. [16] Hekmatshoar R, Majedi S, Bakhtiari K. Catal Commun, 2008, 9: 307[16] Hekmatshoar R, Majedi S, Bakhtiari K. Catal Commun, 2008, 9: 307

    17. [17] Ren Y M, Cai C. Catal Commun, 2008, 9: 1017[17] Ren Y M, Cai C. Catal Commun, 2008, 9: 1017

    18. [18] Heravi M M, Jani B A, Derikvand F, Bamoharram F F, Oskooie H A. Catal Commun, 2008, 10: 272[18] Heravi M M, Jani B A, Derikvand F, Bamoharram F F, Oskooie H A. Catal Commun, 2008, 10: 272

    19. [19] Khurana J M, Kumar S. Tetrahedron Lett, 2009, 50: 4125[19] Khurana J M, Kumar S. Tetrahedron Lett, 2009, 50: 4125

    20. [20] Sabitha G, Arundhathi K, Sudhakar K, Sastry B S, Yadav J S. Synth Commun, 2009, 39: 433[20] Sabitha G, Arundhathi K, Sudhakar K, Sastry B S, Yadav J S. Synth Commun, 2009, 39: 433

    21. [21] Sun W B, Zhang P, Fan J, Chen S H, Zhang Z H. Synth Commun, 2010, 40: 587[21] Sun W B, Zhang P, Fan J, Chen S H, Zhang Z H. Synth Commun, 2010, 40: 587

    22. [22] Wang L M, Shao J H, Tian H, Wang Y H, Liu B. J Fluorine Chem, 2006, 127: 97[22] Wang L M, Shao J H, Tian H, Wang Y H, Liu B. J Fluorine Chem, 2006, 127: 97

    23. [23] Khodaei M M, Bahrami K, Farrokhi A. Synth Commun, 2010, 40: 1492[23] Khodaei M M, Bahrami K, Farrokhi A. Synth Commun, 2010, 40: 1492

    24. [24] Fang D, Zhang H B, Liu Z L. J Heterocycl Chem, 2010, 47: 63[24] Fang D, Zhang H B, Liu Z L. J Heterocycl Chem, 2010, 47: 63

    25. [25] Li Y C, Chen H, Shi C L, Shi D Q, Ji S J. J Comb Chem, 2010, 12: 231[25] Li Y C, Chen H, Shi C L, Shi D Q, Ji S J. J Comb Chem, 2010, 12: 231

    26. [26] Katkar S S, Lande M K, Arbad B R, Gaikwad S T. Chin J Chem, 2011, 29: 199[26] Katkar S S, Lande M K, Arbad B R, Gaikwad S T. Chin J Chem, 2011, 29: 199

    27. [27] Zheng J, Li Y Q. Scholar Research Library, 2011, 3: 381[27] Zheng J, Li Y Q. Scholar Research Library, 2011, 3: 381

    28. [28] Salvi P P, Mandhare A M, Sartape A S, Pawar D K, Han S H, Kolekar S S. C R Chim, 2011, 14: 878[28] Salvi P P, Mandhare A M, Sartape A S, Pawar D K, Han S H, Kolekar S S. C R Chim, 2011, 14: 878

    29. [29] Karami B, Kiani M, Ahmad Hoseini M. Chin J Catal (催化学报), 2014, 35: 1206[29] Karami B, Kiani M, Ahmad Hoseini M. Chin J Catal (催化学报), 2014, 35: 1206

    30. [30] Wei J W, Guo W G, Zhang B Y, Liu Y, Li C. Chin J Catal (催化学报), 2014, 35: 1008[30] Wei J W, Guo W G, Zhang B Y, Liu Y, Li C. Chin J Catal (催化学报), 2014, 35: 1008

    31. [31] Hazeri N, Maghsoodlou M T, Mir F, Kangani M, Saravani H, Mollashahi E. Chin J Catal (催化学报), 2014, 35: 391[31] Hazeri N, Maghsoodlou M T, Mir F, Kangani M, Saravani H, Mollashahi E. Chin J Catal (催化学报), 2014, 35: 391

    32. [32] Kangani M, Hazeri N, Maghsoodlou M, Salahi S. Res Chem Intermed, 2013, doi: 10.107/s11164-013-1365-z[32] Kangani M, Hazeri N, Maghsoodlou M, Salahi S. Res Chem Intermed, 2013, doi: 10.107/s11164-013-1365-z

    33. [33] Mousavi M R, Hazeri N, Maghsoodlou M T, Salahi S, Habibi-Khorassani S M. Chin Chem Lett, 2013, 24: 411[33] Mousavi M R, Hazeri N, Maghsoodlou M T, Salahi S, Habibi-Khorassani S M. Chin Chem Lett, 2013, 24: 411

    34. [34] Noorisadeh F, Maghsoodlou M T, Hazeri N, Kangani M. Res Chem Intermed, 2014, doi: 10.1007/s11164-014-1710-x[34] Noorisadeh F, Maghsoodlou M T, Hazeri N, Kangani M. Res Chem Intermed, 2014, doi: 10.1007/s11164-014-1710-x

    35. [35] Habibi-Khorassani S M, Ebrahimi A, Maghsoodlou M T, Asheri O, Shahraki M, Akbarzadeh N, Ghalandarzehi Y. Int J Chem Kinet, 2013, 45: 596[35] Habibi-Khorassani S M, Ebrahimi A, Maghsoodlou M T, Asheri O, Shahraki M, Akbarzadeh N, Ghalandarzehi Y. Int J Chem Kinet, 2013, 45: 596

    36. [36] Habibi-Khorassani S M, Maghsoodlou M T, Ebrahimi A, Farahani F V, Mosaddeg E, Kazemain M A. Tetrahedron Letters, 2009, 50: 3621[36] Habibi-Khorassani S M, Maghsoodlou M T, Ebrahimi A, Farahani F V, Mosaddeg E, Kazemain M A. Tetrahedron Letters, 2009, 50: 3621

    37. [37] Habibi-Khorassani S M, Ebrahimi A, Maghsoodlou M T, Zakarianezhad M, Ghasempour H, Ghahghayi Z. Curr Org Chem, 2011, 15: 942[37] Habibi-Khorassani S M, Ebrahimi A, Maghsoodlou M T, Zakarianezhad M, Ghasempour H, Ghahghayi Z. Curr Org Chem, 2011, 15: 942

    38. [38] Dehdab M, Habibi-Khorassani S M, Shahraki M. Catal Lett, 2014, 144: 1790[38] Dehdab M, Habibi-Khorassani S M, Shahraki M. Catal Lett, 2014, 144: 1790

    39. [39] Jin T S, Wang A Q, Wang X, Zhang J S, Li T S. Synlett, 2004: 871[39] Jin T S, Wang A Q, Wang X, Zhang J S, Li T S. Synlett, 2004: 871

    40. [40] Gurumurthi S, Sundari V, Valliappan R. E-J Chem, 2009, 6: S466[40] Gurumurthi S, Sundari V, Valliappan R. E-J Chem, 2009, 6: S466

    41. [41] Schwartz L M, Gelb R I. Anal Chem, 1978, 50: 1592[41] Schwartz L M, Gelb R I. Anal Chem, 1978, 50: 1592

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  • 发布日期:  2015-05-20
  • 收稿日期:  2014-12-16
  • 网络出版日期:  2015-01-19
通讯作者: 陈斌, bchen63@163.com
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