• صفحه اصلی
  • Nano-SiO2/Taurine as a new natural based catalyst for synthesis of hexahydroquinolines derivative

اشتراک گذاری

آدرس مقاله


کد مقاله : IJC-2205-1936 (R1) بازدید : 81 صفحه: 365 - 372

10.30495/ijc.2022.1959104.1936

نوع مقاله: پژوهشی

Nano-SiO2/Taurine as a new natural based catalyst for synthesis of hexahydroquinolines derivative

محورهای موضوعی : Iranian Journal of Catalysis

Saeed Sharifi Sharifabad 1 , Bi Bi Fatemeh Mirjalili 2 , Abdolhamid Bamoniri 3

1 - Department of Chemistry, College of Science, Yazd University, Yazd, P.O. Box 89195-741, Iran
2 - Department of Chemistry, College of Science, Yazd University, Yazd, P.O. Box 89195-741, Iran
3 - Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, Iran

تاریخ دریافت : 1401/03/11 تاریخ پذیرش : 1401/06/15 تاریخ انتشار : 1401/06/10

کلید واژه: ethyl acetoacetate, Dimedone, Nano-SiO2/Taurine, hexahydroquinoline,

چکیده مقاله :

In this research work, Nano-SiO2/Taurine was synthesized and characterized by FT-IR, energy dispersive X-ray analysis (EDX), scanning electron microscopy (SEM), X-ray diffraction patterns (XRD) ,Thermogravimetric analysis (TGA) and MAP analysis. Nano-SiO2/Taurine has considerable benefits such as simple preparation protocol, simple handling, high acidic property, reusability and high stability. Nano-SiO2/Taurine was used as a catalyst for the synthesis of hexahydroquinolines by the reaction of ethyl acetoacetate, dimedone and ammonium acetate with various aldehydes. These reactions were carried out under solvent-free conditions at 85 °C. The present protocol is simple, eco-friendly and efficient. The hexahydroquinolines were produced at high yields and short reaction times.

چکیده انگلیسی:

منابع و مأخذ:


  1. Abdelmoniem, M. G. M. Abdelrahman, S. A. S. Ghozlan, I. A. Abdelhamid. J. heterocycl. Chem. 56 (2019) 3387.
    2.
  2. S. Reddy, C. Lagishetti, I. N. C. Kiran, H. You, Y. He, Org. Lett. 18 (2016) 3818.
    3.
  3. You, S. R. Vegi, C. Lagishetti, S. Chen, R. S. Reddy, X. Yang, J.Guo, C. Wang, Y. He, J. Org. Chem. 83 (2018) 4119.
    4.
  4. Lagishetti, S. Banne, H. You, M. Tang, J. Guo, Qi, Y. He, Org. Lett. 21 (2019) 5301.
    5.
  5. S. Reddy, S. Zheng, C. Lagishetti, H. You, He, RSC Adv., 6 (2016) 68199.
    6.
  6. Abdelmoniem, M. F. Mohamed, D. M. Abdelmoniem, S. A. S. Ghozlan, I. A. Abdelhamid, Anticancer Agents Med. Chem., 19 (2019) 875.
    7.
  7. Ghorbani‐Choghamarani, B. Tahmasbi, P. Moradi, N. Havasi, Appl. Organomet. Chem. 30 (2016) 619.
    8.
  8. N. Kalaria, S.P. Satasia, D.K. Raval, New J. Chem. 38 (2014) 2902.
    9.
  9. M. Vahdat, F. Chekin, M. Hatami, M. Khavarpour, S. Baghery, Z. Roshan-Kouhi, Chinese J. Catal. 34 (2013) 758.
    10.
  10. Saha, A.K. Pal, Tetrahedron lett. 52 (2011) 4872.
    11.
  11. Ghorbani-Choghamarani, B. Tahmasbi, New J. Chem. 40 (2016) 1205.
    12.
  12. -J. Ji, Z.-Q. Jiang, J. Lu, T.-P. Loh, Synlett. 2004 (2004) 0831.
    13.
  13. M. Heravi, K. Bakhtiari, N.M. Javadi, F.F. Bamoharram, M. Saeedi, H.A. Oskooie, J. Mol. Catal. A Chem. 264 (2007) 50.
    14.
  14. Kumar, P. Sharma, K.K. Kapoor, M.S. Hundal, Tetrahedron 64 (2008) 536.
    15.
  15. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, J. Afsar, A. Zare, V. Khakyzadeh, M. H. Beyzavi Chinese J. Catal. 34 (2013) 1936-1944.
    16.
  16. -J. Song, Z.-X. Shan, Y. Jin, Synth. Commun. 40 (2010) 3067.
    17.
  17. Adibi, H.A. Samimi, M. Beygzadeh, Catal. Commun. 8 (2007) 2119.
    18.
  18. VM, S. SA, S. MS, Bull. Catal. Soc. India 6 (2007) 125.
    19.
  19. Raghu, S.R. Ch, Chem. Lett 19 (2008) 775.
    20.
  20. L. Donelson, R.A. Gibbs, S.K. De, J. Mol. Catal. A Chem. 256 (2006) 309.
    21.
  21. Rostamnia, A. Nuri, H. Xin, A. Pourjavadi, S.H. Hosseini, Tetrahedron Lett. 54 (2013) 3344.
    22.
  22. Rostamnia, H. Xin, X. Liu, K. Lamei, J. Mol. Catal. A Chem. 374 (2013) 85.
    23.
  23. -J. Yü, S. Wu, X.-M. Zhao, C.-W. Lü, Res. Chem. Intermed. 43 (2017) 3121.
    24.
  24. Tabrizian, A. Amoozadeh, J. Chinese Chem. Soc. 64 (2017) 331.
    25.
  25. Khazaei, L. Jafari‐Ghalebabakhani, E. Ghaderi, M. Tavasoli, A.R. Moosavi‐Zare, Appl. Organometal. Chem. 31 (2017) e3815.
    26.
  26. Amoozadeh, S. Rahmani, M. Bitaraf, F.B. Abadi, E. Tabrizian, New J. Chem. 40 (2016) 770.
    27.
  27. Khazaei, N. Sarmasti, J.Y. Seyf, M. Tavasoli, RSC Adv. 5 (2015) 101268.
    28.
  28. R. Moosavi-Zare, M.A. Zolfigol, M. Zarei, A. Zare, J. Afsar, Appl. Catal. A. 505 (2015) 224.
    29.
  29. Amoozadeh, S. Golian, S. Rahmani, RSC Adv. 5 (2015) 45974.
    30.
  30. Zare, F. Abi, A.R. Moosavi-Zare, M.H. Beyzavi, M.A. Zolfigol, J. Mol. Liq. 178 (2013) 113.
    31.
  31. Ke, X. Zhou, H. Gao, G. Hao, L. Xiao, T. Chen, J. Liu, W. Jiang, Mater. Des. 140 (2018) 179.
    32.
  32. J. Song, Z.-X. Shan,   Y. Jin, Synth. commun. 40 (2010) 3067.
    33.
  33. Rostamnia, H. Xin, Appl. Organomet. Chem. 28 (2014) 359.
    34.
  34. Doustkhah, S. Rostamnia, A. Hassankhani, J. Porous Mater. 23 (2016) 549.
    35.
  35. Rostamnia, A. Hassankhani, H.G. Hossieni, B. Gholipour, H. Xin, J. Mol. Catal. A Chem. 395 (2014) 463.
    36.
  36. Rostamnia, A. Hassankhani, Synlett. 25 (2014) 2753.
    37.
  37. Sobhani, F. Zarifi, J. Skibsted, New J. Chem. 41 (2017) 6219.
    38.
  38. Akbarpoor, A. Khazaei, J. Yousefi Seyf, N. Sarmasti, M. Mahmoudiani Gilan,  Res. Chem. Intermed.46 (2020)1539.
    39.
  39. Huxtable, Physiol. Rev. 72 (1992) 101.
    40.
  40. Cook, Tenside, surfactants, detergents 35 (1998) 52.
    41.
  41. Daneshvar, F. Shirini, M. Safarpoor, N. Langarudi, R. Karimi-Chayjani, Bioorgan. Chem. 77 (2018) 68.
    42.
  42. -L. Chen, K.-C. Fang, J.-Y. Sheu, S.-L. Hsu, C.-C. Tzeng, J. Med. Chem. 44 (2001) 2374.
    43.
  43. Moosavi-Zare, M. Zarei, A. Zare, V. Khakyzadeh and A. Hasaninejad. Appl. Catal. A. 467 (2013) 61.
    44.
  44. Şimşek, U.B. İsmailoğlu, C. Şafak, İ. Sahin-Erdemli, Il Farmaco 55 (2000) 665.
    45.
  45. O. Kappe, Tetrahedron 49 (1993) 6937.
    46.
  46. D. Larsen, E.G. Corley, A.O. King, J.D. Carroll, P. Davis, T.R. Verhoeven, P.J. Reider, M. Labelle, J.Y. Gauthier, Y.B. Xiang, J. Org. Chem. 61 (1996) 3398.
    47.
  47. R. Hajipour, M. Karimzadeh, H. Tavallaei, J. Iran. Chem. Soc. 12 (2015) 987.
    48.
  48. Tajbakhsh, H. Alinezhad, M. Norouzi, S. Baghery, M. Akbari, J. Mol. Liq. 177 (2013) 44.
    49.
  49. -M. Wang, J. Sheng, L. Zhang, J.-W. Han, Z.-Y. Fan, H. Tian, C.-T. Qian, Tetrahedron. 61 (2005) 1539.
    50.
  50. R. Cherkupally, R. Mekala, Chem. Pharm. Bull. 56 (2008) 1002.
    51.
  51. Kumar, R.A. Maurya, Tetrahedron 63 (2007) 1946.
    52.
  52. S. Gadekar, S.S. Katkar, S.R. Mane, B.R. Arbad, M.K. Lande, Bull. Korean Chem. Soc. 30 (2009) 2532.
    53.
  53. Azarifar, Y. Abbasi, M. Jaymand, M.A. Zolfigol, M. Ghaemi, O. Badalkhani, J. Organomet. Chem. 895 (2019) 55.
    54.
  54. Mobinikhaledi, N. Foroughifar, M.A.B. Fard, H. Moghanian, S. Ebrahimi, M. Kalhor, Synth. Commun. 39 (2009) 1166.
    55.
  55. Yosefzadeh, M. Mokhtary, Iran. J. Catal. 6 (2016) 153.
    56.
  56. Maleki, R. Tayebee, M. Kermanian, S. Sedigh Ashrafi, J. Mex. Chem. 57 (2013) 290.
    57.
  57. Khabazzadeh, E.T. Kermani, D. Afzali, A. Amiri, A. Jalaladini, Arab. J. Chem. 5 (2012) 167.
    58.

سکوی نشر دانش

سند یا سکوی نشر دانش ،سامانه ای جهت مدیریت حوزه علمی و پژوهشی نشریات دانشگاه آزاد می باشد

پیوندهای سایت

مراکز مرتبط

پشتیبانی

صفحات رسمی

حقوق این وب‌سایت متعلق به سامانه مدیریت نشریات دانشگاه آزاد اسلامی است.
حق نشر © 1403-1400

صفحه اصلی| عضویت/ ورود| درباره سند| تماس با ما|
[English] [العربية] [en] [ar]