Advertisement

Journal of the Iranian Chemical Society

, Volume 17, Issue 2, pp 247–282 | Cite as

Recent advances in the application of acetophenone in heterocyclic compounds synthesis

  • Ghodsi Mohammadi ZiaraniEmail author
  • Zohreh Kheilkordi
  • Fatemeh Mohajer
Review
  • 48 Downloads

Abstract

Acetophenone is an interesting synthon in the most organic reactions. Acetophenone has been utilized in the synthesis of many heterocyclic compounds. Acetophenone and most of its derivatives are commercially available or readily accessible and hence are ideal synthon for multicomponent reactions including the three- and four-component reactions. Also, the biological activities of some compounds were studied. Herein, we want to review the application of the acetophenone as starting material in the synthesis of various heterocyclic compounds including fused and five-, six-, seven-membered rings via multicomponent reactions.

Graphic abstract

Keywords

Acetophenone Heterocyclic compounds Multicomponent reactions Five-membered rings Six-membered rings 

Abbreviations

NBSac

N-Bromosaccharin

THF

Tetrahydrofuran

Yb(OTF)

Ytterbium(III) triflate

TBBDA-MNPs@SiO2-Pr-AP

N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide [TBBDA], poly(N,N′-dibromo-N-ethylbenzene-1,3-disulfonamide) [PBBS]

BIL

Basic ionic liquid

Y(OTf)3

Yttrium triflate

DMF-DMA

N,N-dimethylformamide-dimethylacetal

NBS

N-bromosuccinimide

BDMS

Bromodimethylsulfonium bromide

TCRT

Three-component ring transformation

MWCNTs

Metal oxide nanocomposites

SBA-Pr-SO3H

Sulfonic acid functionalized silica

STO

Sulfated tin oxide

CAN

Ceric ammonium nitrate

FeAlP-550

Amorphous mesoporous iron aluminophosphate

TBBDA

N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide

[Bmim]HSO4

1-Butyl-3-methylimidazolium hydrogen sulfate

PFPAT

Penta fluorophenylammoniumtriflate

Wet-TCT

Wet 2,4,6-trichloro-1,3,5-triazine

[Hmim]NO3−[Bmim]BF3

1-Methylimidazolium nitrate in 1-butyl-3-methylimidazolium tetrafluoroborate

GO

Graphene oxide

Notes

Acknowledgements

We are grateful for financial support from the Research Council of Alzahra University.

References

  1. 1.
    T. Liu, H. Cheng, L. Sun, F. Liang, C. Zhang, Z. Ying, F. Zhao, Appl. Catal. A. 512, 9 (2016)CrossRefGoogle Scholar
  2. 2.
    A.K. Suresh, M.M. Sharma, T. Sridhar, Ind. Eng. Chem. Res. 39, 3958 (2000)CrossRefGoogle Scholar
  3. 3.
    B. Sarkar, P. Prajapati, R. Tiwari, R. Tiwari, S. Ghosh, S.S. Acharyya, T. Sasaki, Green Chem. 14, 2600 (2012)CrossRefGoogle Scholar
  4. 4.
    L. Chen, B. Li, D. Liu, Catal. Lett. 144, 1053 (2014)CrossRefGoogle Scholar
  5. 5.
    A. Tanaka, T. Terasawa, H. Hagihara, Y. Sakuma, N. Ishibe, M. Sawada, H. Tanaka, J. Med. Chem. 41, 2390 (1998)PubMedCrossRefPubMedCentralGoogle Scholar
  6. 6.
    P.C. Astles, C. Brealey, T.J. Brown, V. Facchini, C. Handscombe, N.V. Harris, C. Sargent, J. Med. Chem. 41, 2732 (1998)PubMedCrossRefPubMedCentralGoogle Scholar
  7. 7.
    F. Garrido, S. Raeppel, A. Mann, M. Lautens, Tetrahedron Lett. 42, 265 (2001)CrossRefGoogle Scholar
  8. 8.
    O. Renault, P. Dallemagne, S. Rault, Org. Prep. Proced. Int. 31, 324 (1999)CrossRefGoogle Scholar
  9. 9.
    Y. Wang, J. Zhang, X. Wang, M. Antonietti, H. Li, Angew. Chem. Int. Ed. 49, 3356 (2010)CrossRefGoogle Scholar
  10. 10.
    K.N. Bhagya, V. Gayathri, J. Porous Mater. 21, 197 (2014)CrossRefGoogle Scholar
  11. 11.
    Y. He, Z. Rui, H. Ji, Catal. Commun. 14, 77 (2011)CrossRefGoogle Scholar
  12. 12.
    J.D. Sunderhaus, S.F. Martin, Chem. Eur. J. 15, 1300 (2009)PubMedCrossRefPubMedCentralGoogle Scholar
  13. 13.
    X. Yang, Y.B. Zhang, Z.N. Wu, X.Q. Zhang, J.W. Jiang, Y.L. Li, G.C. Wang, Fitoterapia 105, 156 (2015)PubMedCrossRefPubMedCentralGoogle Scholar
  14. 14.
    F. Epifano, S. Fiorito, S. Genovese, Phytochemistry 95, 12 (2013)PubMedCrossRefPubMedCentralGoogle Scholar
  15. 15.
    B. Ryu, H.M. Kim, J.H. Woo, J.H. Choi, D.S. Jang, Fitoterapia 115, 46 (2016)PubMedCrossRefPubMedCentralGoogle Scholar
  16. 16.
    G. Mohammadi Ziarani, P. Hajiabbasi, Heterocycles 87, 1415 (2013)CrossRefGoogle Scholar
  17. 17.
    G. Mohammadi Ziarani, N. Hosseini Nasab, N. Lashgari, RSC Adv. 6, 38827 (2016)CrossRefGoogle Scholar
  18. 18.
    G. Mohammadi Ziarani, F. Aleali, N. Lashgari, RSC Adv. 6, 50895 (2016)CrossRefGoogle Scholar
  19. 19.
    T. Ahmadi, G. Mohammadi Ziarani, P. Gholamzadeh, H. Mollabagher, Tetrahedron: Asymmetry. 28, 708 (2017)CrossRefGoogle Scholar
  20. 20.
    G. Mohammadi Ziarani, R. Moradi, M. Zandiyeh, N. Lashgari, Heterocycles 96, 381 (2018)CrossRefGoogle Scholar
  21. 21.
    G. Mohammadi Ziarani, R. Moradi, N. Lashgari, Arkivoc 2016, 1 (2016)Google Scholar
  22. 22.
    G. Mohammadi Ziarani, R. Moradi, N. Lashgari, Tetrahedron: Asymmetry 26, 517 (2015)CrossRefGoogle Scholar
  23. 23.
    G. Mohammadi Ziarani, P. Gholamzadeh, P. Asadiatouei, N. Lashgari, J. Mol. Catal. B. 122, 93 (2015)CrossRefGoogle Scholar
  24. 24.
    G. Mohammadi Ziarani, P. Gholamzadeh, N. Lashgari, P. Hajiabbasi, Arkivoc 2013, 470 (2013)CrossRefGoogle Scholar
  25. 25.
    R.A. Irgashev, V.Y. Sosnovskikh, N. Kalinovich, O. Kazakova, G.V. Röschenthaler, Tetrahedron Lett. 50, 4903 (2009)CrossRefGoogle Scholar
  26. 26.
    C. Le Floch, E. Le Gall, S. Sengmany, P. Renevret, E. Leonel, T. Martens, T. Cresteil, Eur. J. Org. Chem. 89, 654 (2015)Google Scholar
  27. 27.
    Z. Li, R. Li, M. Gan, L. Jiang, Z. Li, Tetrahedron Lett. 56, 5541 (2015)CrossRefGoogle Scholar
  28. 28.
    K. Vaarla, R.K. Kesharwani, K. Santosh, R.R. Vedula, S. Kotamraju, M.K. Toopurani, Bioorg. Med. Chem. Lett. 25, 5797 (2015)PubMedCrossRefPubMedCentralGoogle Scholar
  29. 29.
    K. Rad-Moghadam, S.C. Azimi, Tetrahedron 68, 9706 (2012)CrossRefGoogle Scholar
  30. 30.
    P. Yan, J. Liu, Q. Sun, J. Yao, Z. Xue, C. Wang, J. Chem. Res. 37, 323 (2013)CrossRefGoogle Scholar
  31. 31.
    H. Yahyavi, M.M. Heravi, M. Mahdavi, Tetrahedron Lett. 59, 94 (2018)CrossRefGoogle Scholar
  32. 32.
    R. Kaur, K. Kumar, Chem. Heterocycl. Compd. 54, 700 (2018)CrossRefGoogle Scholar
  33. 33.
    R. Mishra, A. Jana, A.K. Panday, L.H. Choudhury, Org. Biomol. Chem. 16, 3289 (2018)PubMedCrossRefPubMedCentralGoogle Scholar
  34. 34.
    P. Hazarika, S.D. Sharma, D. Konwar, Catal. Commun. 9, 2398 (2008)CrossRefGoogle Scholar
  35. 35.
    H. Alinezhad, S. Fallahi, Chin. Chem. Lett. 23, 927 (2012)CrossRefGoogle Scholar
  36. 36.
    A. Saeed, S. Zaman, M. Bolte, Synth. Commun. 38, 2185 (2008)CrossRefGoogle Scholar
  37. 37.
    A. Guirado, B. Martiz, R. Andreu, D. Bautista, Tetrahedron 67, 5811 (2011)CrossRefGoogle Scholar
  38. 38.
    Y. Yang, M. Gao, C. Deng, D.X. Zhang, L.M. Wu, W.M. Shu, A.X. Wu, Tetrahedron 68, 6257 (2012)CrossRefGoogle Scholar
  39. 39.
    Y.C. Wang, H.S. Wang, G.B. Huang, F.P. Huang, K. Hu, Y.M. Pan, Tetrahedron 70, 1621 (2014)CrossRefGoogle Scholar
  40. 40.
    A.A. Amer, A.H. Moustafa, Synlett 27, 1703 (2016)CrossRefGoogle Scholar
  41. 41.
    M. Nikpassand, L.Z. Fekri, S. Sanagou, Dyes Pigments 136, 140 (2017)CrossRefGoogle Scholar
  42. 42.
    S. Zaher, L. Christ, M.A. El Rahim, A. Kanj, I. Karamé, Mol. Catal. 438, 204 (2017)CrossRefGoogle Scholar
  43. 43.
    Z. Zarnegar, M. Sadeghi, R. Alizadeh, J. Safai, J. Mol. Liq. 255, 76 (2018)CrossRefGoogle Scholar
  44. 44.
    R. Ghorbani-Vaghei, S. Alavinia, Z. Merati, V. Izadkhah, Appl. Organomet. Chem. 32, e4127 (2018)CrossRefGoogle Scholar
  45. 45.
    Y.P. Zhu, J.J. Yuan, Q. Zhao, M. Lian, Q. He, M.C. Gao, Y. Liu, A.X. Yang, Wu, Tetrahedron. 68, 173 (2012)CrossRefGoogle Scholar
  46. 46.
    J. Safari, S.H. Banitaba, S.D. Khalili, Chin. J. Chem. 32, 1850 (2011)Google Scholar
  47. 47.
    S. Ray, M. Brown, A. Bhaumik, A. Dutta, C. Mukhopadhyay, Green Chem. 15, 1910 (2013)CrossRefGoogle Scholar
  48. 48.
    Y. Liu, X. Yuan, X. Guo, X. Zhang, B. Chen, Tetrahedron 74, 6057 (2018)CrossRefGoogle Scholar
  49. 49.
    A. Alanthadka, S.D. Elango, P. Thangavel, N. Subbiah, S. Vellaisamy, U.M. Chockalingam, Catal. Commun. 125, 26 (2019)CrossRefGoogle Scholar
  50. 50.
    B. Han, Z. Zheng, D. Zheng, L. Zhang, P. Cui, J. Shi, C. Li, Synth. Commun. 49, 2512 (2019)CrossRefGoogle Scholar
  51. 51.
    D. Khan, N. Ahmed, M.A. Alsharif, M.I. Alahmdi, S. Mukhtar, Chem. Sel. 4, 7585 (2019)Google Scholar
  52. 52.
    H.R. Farmani, M.H. Mosslemin, B. Sadeghi, Mol. Divers. 22, 743 (2018)PubMedCrossRefPubMedCentralGoogle Scholar
  53. 53.
    S. Damavandi, Synth. React. Inorg. 42, 1415 (2012)CrossRefGoogle Scholar
  54. 54.
    S. Bhattacharjee, D.K. Das, A.T. Khan, Tetrahedron Lett. 56, 2412 (2015)CrossRefGoogle Scholar
  55. 55.
    M.V. Reddy, B.S. Kumar, K.T. Lim, B.G. Cho, Y.T. Jeong, Tetrahedron Lett. 57, 476 (2016)CrossRefGoogle Scholar
  56. 56.
    W.S. Hamama, M.E. Ibrahim, A.A. Gooda, H.H. Zoorob, Synth. Commun. 47, 224 (2017)CrossRefGoogle Scholar
  57. 57.
    S. Sharifi, M.T. Maghsoudlou, N. Hazeri, F. Rostami-Charati, J. Chin. Chem. Soc. (2019).  https://doi.org/10.1002/jccs.201800282 CrossRefGoogle Scholar
  58. 58.
    S. Damavandi, R. Sandaroos, M. Vafaeei, H.R. Molaei, Chin. Chem. Lett. 23, 253 (2012)CrossRefGoogle Scholar
  59. 59.
    C.V. Asokan, E.R. Anabha, A.D. Thomas, A.M. Jose, K.C. Lethesh, M. Prasanth, K.U. Krishanraj, Tetrahedron Lett. 48, 5641 (2007)CrossRefGoogle Scholar
  60. 60.
    W. Su, S. Guo, Z. Hong, Tetrahedron Lett. 51, 5718 (2010)CrossRefGoogle Scholar
  61. 61.
    A.M. Serry, S. Luik, S. Laufer, A.H. Abadi, J. Comb. Chem. 12, 559 (2010)PubMedCrossRefPubMedCentralGoogle Scholar
  62. 62.
    A. Patti, S. Pedotti, Tetrahedron 66, 5607 (2010)CrossRefGoogle Scholar
  63. 63.
    E. Kowsari, M. Mallakmohammadi, Ultrason. Sonochem. 18, 447 (2011)PubMedCrossRefPubMedCentralGoogle Scholar
  64. 64.
    A.R. Khosropour, I. Mohammadpoor-Baltork, F. Kiani, Comptes Rendus Chim. 14, 441 (2011)CrossRefGoogle Scholar
  65. 65.
    J. Tang, L. Wang, Y. Yao, L. Zhang, W. Wang, Tetrahedron Lett. 52, 509 (2011)CrossRefGoogle Scholar
  66. 66.
    H. Sheibani, K. Saidi, M. Abbasnejad, A. Derakhshani, I. Mohammadzadeh, Arab. J. Chem. 9, S901 (2016)CrossRefGoogle Scholar
  67. 67.
    D. Khalili, Tetrahedron Lett. 57, 1721 (2016)CrossRefGoogle Scholar
  68. 68.
    S.S. Mansoor, K. Aswin, K. Logaiya, S.P.N. Sudhan, J. Saudi Chem. Soc. 20, 517 (2016)CrossRefGoogle Scholar
  69. 69.
    S.S. Mansoor, K. Aswin, K. Logaiya, S.P.N. Sudhan, Rasayan J. Chem. 10, 1334 (2017)Google Scholar
  70. 70.
    M. Torabi, M. Yarie, M.A. Zolfigol, Appl. Organomet. Chem. 33, e4933 (2019)CrossRefGoogle Scholar
  71. 71.
    Z. Kheilkordi, G.M. Ziarani, S. Bahar, A. Badiei, J. Iran. Chem. Soc. 16, 365 (2019)CrossRefGoogle Scholar
  72. 72.
    M.A. Zolfigol, M. Yarie, Appl. Organomet. Chem. 31, e3598 (2017)CrossRefGoogle Scholar
  73. 73.
    S. Kalhor, M. Yarie, M. Rezaeivala, M.A. Zolfigol, Res. Chem. Intermed. 45, 3453 (2019)CrossRefGoogle Scholar
  74. 74.
    J. Safari, S.H. Banitaba, S.D. Khalili, Ultrason. Sonochem. 19, 1061 (2012)PubMedCrossRefPubMedCentralGoogle Scholar
  75. 75.
    A. Yahyazadeh, E. Abbaspour-Gilandeh, M. Aghaei-Hashjin, Catal. Lett. 148, 1254 (2018)CrossRefGoogle Scholar
  76. 76.
    A.A. Amer, A.A. Abdelhamid, J. Heterocycl. Chem. 54, 3126 (2017)CrossRefGoogle Scholar
  77. 77.
    D. Addla, B. Sridhar, A. Devi, S. Kantevari, Bioorg. Med. Chem. Lett. 22, 7475 (2012)PubMedCrossRefPubMedCentralGoogle Scholar
  78. 78.
    B. Maleki, D. Azarifar, H. Veisi, S.F. Hojati, H. Salehabadi, R.N. Yami, Chin. Chem. Lett. 21, 1346 (2010)CrossRefGoogle Scholar
  79. 79.
    M.R.M. Shafiee, R. Moloudi, M. Ghashang, APCBEE Proc. 1, 221 (2012)CrossRefGoogle Scholar
  80. 80.
    N. Montazeri, S. Mahjoob, Chin. Chem. Lett. 23, 419 (2012)CrossRefGoogle Scholar
  81. 81.
    A.R. Moosavi-Zare, M.A. Zolfigol, S. Farahmand, A. Zare, A.R. Pourali, Synlett 25, 193 (2014)CrossRefGoogle Scholar
  82. 82.
    E. Tabrizian, A. Amoozadeh, S. Rahmani, E. Imanifar, S. Azhari, M. Malmir, Chin. Chem. Lett. 26, 1278 (2015)CrossRefGoogle Scholar
  83. 83.
    M.A. Zolfigol, M. Safaiee, F. Afsharnadery, N. Bahrami-Nejad, S. Baghery, S. Salehzadeh, F. Maleki, RSC Adv. 5, 100546 (2015)CrossRefGoogle Scholar
  84. 84.
    M. Safaiee, B. Ebrahimghasri, M.A. Zolfigol, S. Baghery, A. Khoshnood, D.A. Alonso, New J. Chem. 42, 12539 (2018)CrossRefGoogle Scholar
  85. 85.
    J. Safari, Z. Zarnegar, M.B. Borujeni, Chem. Pap. 67, 688 (2013)CrossRefGoogle Scholar
  86. 86.
    H. Wang, W. Zhao, J. Du, F. Wei, Q. Chen, X. Wang, RSC Adv. 9, 5158 (2019)CrossRefGoogle Scholar
  87. 87.
    A. Davoodnia, B. Razavi, N. Tavakoli-Hoseini, J. Chem. 9, 2037 (2012)Google Scholar
  88. 88.
    S.H. Doan, N.K. Tran, P.H. Pham, V.H. Nguyen, N.N. Nguyen, P.T. Ha, N.T. Phan, Eur. J. Org. Chem. 13, 2382 (2019)CrossRefGoogle Scholar
  89. 89.
    H. Tan, J. Wang, Y. Zhang, Y. Xing, Q. Sun, R. Li, Tetrahedron 69, 8299 (2013)CrossRefGoogle Scholar
  90. 90.
    B. Li, C. Guo, X. Fan, J. Zhang, X. Zhang, Tetrahedron Lett. 55, 5944 (2014)CrossRefGoogle Scholar
  91. 91.
    M.M. Sarmah, D. Prajapati, RSC Adv. 4, 22955 (2014)CrossRefGoogle Scholar
  92. 92.
    H. Alinezhad, S.M. Tavakkoli, P. Biparva, Chin. J. Chem. 35, 560 (2014)Google Scholar
  93. 93.
    P.K. Tapaswi, C. Mukhopadhyay, Arkivoc. 2011, 287 (2011)CrossRefGoogle Scholar
  94. 94.
    S. Tu, B. Jiang, R. Jia, J. Zhang, Y. Zhang, Tetrahedron Lett. 48, 1369 (2007)CrossRefGoogle Scholar
  95. 95.
    S. Khaksar, M. Gholami, J. Mol. Liq. 196, 159 (2014)CrossRefGoogle Scholar
  96. 96.
    F. Tamaddon, S. Ghazi, M.R. Noorbala, J. Mol. Catal. B Enzymatic 127, 89 (2016)CrossRefGoogle Scholar
  97. 97.
    S. Baluja, R. Talaviya, J. Mol. Liq. 223, 436 (2016)CrossRefGoogle Scholar
  98. 98.
    S.M. Ghodse, V.N. Telvekar, Tetrahedron Lett. 58, 524 (2017)CrossRefGoogle Scholar
  99. 99.
    S. Ladraa, M. Chioua, A. Belfaitah, J. Heterocycl. Chem. 54, 603 (2017)CrossRefGoogle Scholar
  100. 100.
    H. Asahara, Proc. Eng. 174, 1046 (2017)CrossRefGoogle Scholar
  101. 101.
    S. Adhikari, O. Hussain, R.M. Phillips, M.R. Kollipara, J. Organomet. Chem. 854, 27 (2018)CrossRefGoogle Scholar
  102. 102.
    S. Nandi, M.M. Islam, M. Saha, S. Mitra, S. Khatua, A.K. Pal, Synth. Commun. 46, 1461 (2016)CrossRefGoogle Scholar
  103. 103.
    T.S. Jiang, X. Wang, X. Zhang, Tetrahedron Lett. 59, 2979 (2018)CrossRefGoogle Scholar
  104. 104.
    S. Khan, M. Agasar, A. Ghosh, R.S. Keri, Org. Prep. Proced. Int. 51, 153 (2019)CrossRefGoogle Scholar
  105. 105.
    S.K. De, Tetrahedron Lett. 45, 2339 (2004)CrossRefGoogle Scholar
  106. 106.
    Z.T. Wang, L.W. Xu, C.G. Xia, H.Q. Wang, Tetrahedron Lett. 45, 7951 (2004)CrossRefGoogle Scholar
  107. 107.
    J. Safari, S. Gandomi-Ravandi, J. Mol. Catal. A: Chem. 373, 72 (2013)CrossRefGoogle Scholar
  108. 108.
    J. Safari, S. Gandomi-Ravandi, J. Mol. Struct. 1074, 71 (2014)CrossRefGoogle Scholar
  109. 109.
    M.A. Pasha, S. Nagashree, Ultrason. Sonochem. 21, 1279 (2014)PubMedCrossRefPubMedCentralGoogle Scholar
  110. 110.
    G. Mohammadi Ziarani, M. Azizi, P. Hajiabbasi, A. Badiei, Química Nova. 38, 466 (2015)Google Scholar
  111. 111.
    R. Khanivar, A. Zare, Z. Naturforsch. 73, 635 (2018)CrossRefGoogle Scholar
  112. 112.
    U.P. Singh, H.R. Bhat, R.K. Singh, C. R. Chim. 16, 462 (2013)CrossRefGoogle Scholar
  113. 113.
    R.L. Magar, P.B. Thorat, P.B. Thorat, V.V. Thorat, B.R. Patil, R.P. Pawar, Chin. Chem. Lett. 24, 1070 (2013)CrossRefGoogle Scholar
  114. 114.
    S.J. Robinson, J.P. Petzer, A.L. Rousseau, G. Terre’Blanche, A. Petzer, A.C. Lourens, Bioorg. Med. Chem. Lett. 26, 734 (2016)PubMedCrossRefPubMedCentralGoogle Scholar
  115. 115.
    F. Qiu, J. Yang, D. Shi, Q. Zhang, J. Li, Tetrahedron Lett. 57, 1210 (2016)CrossRefGoogle Scholar
  116. 116.
    S.A. Jadhav, A.P. Sarkate, M.G. Shioorkar, D.B. Shinde, Synth. Commun. 47, 1661 (2017)CrossRefGoogle Scholar
  117. 117.
    B. Kumar, P. Sharma, V.P. Gupta, M. Khullar, S. Singh, N. Dogra, V. Kumar, Bioorg. Chem. 78, 130 (2018)PubMedCrossRefPubMedCentralGoogle Scholar
  118. 118.
    B. Niu, C. You, B. Huang, M. Cai, Catal. Commun. 123, 11 (2019)CrossRefGoogle Scholar
  119. 119.
    C.S. Radatz, R.B. Silva, G. Perin, E.J. Lenardão, R.G. Jacob, D. Alves, Tetrahedron Lett. 52, 4132 (2011)CrossRefGoogle Scholar
  120. 120.
    M.N. Timofeeva, V.N. Panchenko, S.A. Prikhod’ko, A.B. Ayupov, Y.V. Larichev, N.A. Khan, S.H. Jhung, J. Catal. 354, 128 (2017)CrossRefGoogle Scholar
  121. 121.
    A.V. Vijayasankar, S. Deepa, B.R. Venugopal, N. Nagaraju, Chin. J. Catal. 31, 1321 (2010)CrossRefGoogle Scholar
  122. 122.
    R. Ghorbani-Vaghei, Z. Toghraei-Semiromi, M. Amiri, R. Karimi-Nami, Mol. Divers. 17, 307 (2013)PubMedCrossRefPubMedCentralGoogle Scholar
  123. 123.
    P. Kour, V.P. Singh, B. Khajuria, T. Singh, A. Kumar, Tetrahedron Lett. 58, 4179 (2017)CrossRefGoogle Scholar
  124. 124.
    J. Qiao, B. Liu, Z. Liao, Y. Li, L. Ma, C. Dong, H.B. Zhou, Tetrahedron 70, 3782 (2014)CrossRefGoogle Scholar
  125. 125.
    D. Kour, R. Khajuria, K.K. Kapoor, Tetrahedron Lett. 57, 4464 (2016)CrossRefGoogle Scholar
  126. 126.
    M. Wang, C. Liu, Y. Gu, Tetrahedron 72, 6854 (2016)CrossRefGoogle Scholar
  127. 127.
    L. Suresh, P. Onkara, P.S.V. Kumar, Y. Pydisetty, G.V.P. Chandramouli, Bioorg. Med. Chem. Lett. 26, 4007 (2016)PubMedCrossRefPubMedCentralGoogle Scholar
  128. 128.
    A.H. Moustafa, A.A. Amer, Synth. Commun. 47, 1102 (2017)CrossRefGoogle Scholar
  129. 129.
    J. Gálvez, S. Polo, B. Insuasty, M. Gutiérrez, D. Cáceres, J.H. Alzate-Morales, J. Quiroga, Comput. Biol. Chem. 74, 218 (2018)PubMedCrossRefPubMedCentralGoogle Scholar
  130. 130.
    T. Shi, C. Zerio, J. Sivinski, A.J. Ambrose, K.T. Moore, T. Buckley, E. Chapman, Eur. J. Org. Chem. 20, 3269 (2019)CrossRefGoogle Scholar
  131. 131.
    J. Sun, J. Han, Y. Zhang, Y. Liu, J. Heterocycl. Chem. (2019).  https://doi.org/10.1002/jhet.3618 CrossRefGoogle Scholar
  132. 132.
    V. Ramesh, N.S. Devi, M. Velusamy, S. Shanmugam, Chem. Sel. 4, 3717 (2019)Google Scholar
  133. 133.
    A. Jana, P. Bhaumick, A.K. Panday, R. Mishra, L.H. Choudhury, Org. Biomol. Chem. 17, 5316 (2019)PubMedCrossRefPubMedCentralGoogle Scholar
  134. 134.
    S. Hu, S. Du, Y. Yao, Z. Yang, H. Ren, Z. Chen, Synlett 30, 625 (2019)CrossRefGoogle Scholar
  135. 135.
    P. Zhao, X. Wu, Y. Zhou, X. Geng, C. Wang, Y.D. Wu, A.X. Wu, Org. Lett. 21, 2708 (2019)PubMedCrossRefPubMedCentralGoogle Scholar

Copyright information

© Iranian Chemical Society 2019

Authors and Affiliations

  1. 1.Department of ChemistryAlzahra UniversityTehranIran

Personalised recommendations