Citation: Sun Xiaohua, Sun Chuance, Feng Lijun, Kang Congmin. Recent Progress in the Synthesis of Thieno[2, 3-d]pyrimidine Compounds via Tandem Cyclization[J]. Chinese Journal of Organic Chemistry, ;2020, 40(9): 2626-2640. doi: 10.6023/cjoc202004002 shu

Recent Progress in the Synthesis of Thieno[2, 3-d]pyrimidine Compounds via Tandem Cyclization

College of Chemical Engineering, Qingdao University of Science and Technology, Shandong Province, Qingdao, Shandong 266042

Corresponding author: Kang Congmin, cmkang@qust.edu.cn
Received Date: 1 April 2020
Revised Date: 31 May 2020
Available Online: 19 June 2020
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21272131)the National Natural Science Foundation of China 21272131

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Thieno[2, 3-d]pyrimidine compounds are an important class of organic synthesis intermediates and pharmacologically active molecules, which not only have broad medical application prospect, but also worth researching. Therefore the synthesis of them has attracted much attention. The previous methods mainly apply tandem cyclization or one-pot multi-com-ponent reaction combined with microwave-assisted reaction or new catalysts to reach the purpose of shortening reaction time, reducing steps, enhancing yields and lowering costs. In this paper, the recent progress in the synthesis of thieno[2, 3-d]pyri-midine compounds via tandem cyclization in recent ten years, especially in the latest five years, is reviewed. The problems and limitations faced are discussed, and the development directions are also prospected.
- thieno[2, 3-d]pyrimidine,
- tandem cyclization,
- microwave reaction,
- one-pot multi-component reaction
1. [1]
  Hafez, H. N.; El-gazzar, A. B. A.; Nawwar, G. A. M. Eur. J. Med. Chem. 2010, 45, 1486.
2. [2]
  Ashalatha, B. V.; Narayana, B.; Raj, K. K. V.; Kumari, N. S. Eur. J. Med. Chem. 2007, 42, 722.
3. [3]
  Borate, H. B.; Annadate, R. A.; Vagh, S. S.; Pisal, M. M.; Deokate, S. B.; Arkile, M. A.; Jadhav N. J.; Nawale, L. U.; Sarkar, D. MedChemComm 2015, 6, 2213.
4. [4]
  Al-Taisan, K. M.; Al-Hazimi, H.; Al-Shihry, S. S. Molecules 2010, 15, 3939.
5. [5]
  El-Batanony, N. H. Period. Biol. 2017, 119, 29.
6. [6]
  Bakavoli, M.; Bagherzadeh, G.; Vaseghifar, M.; Shiri, A.; Pordeli, P. J. Chem. Res. 2009, 654.
7. [7]
  Kotaiah, Y.; Harikrishna, N.; Nagaraju, K.; Rao, C. V. Eur. J. Med. Chem. 2012, 58, 341.
8. [8]
  Pedeboscq, S.; Gravier, D.; Casadebaig, F.; Hou, G.; Gissot, A.; Rey, C.; Ichas, F.; Giorgi, F. D.; Lartigue, L.; Pometan, J. P. Bioorg. Med. Chem. 2012, 20, 6726.
9. [9]
  Mavrova, A. T.; Dimov, S.; Yancheva, D.; Rangelov, M.; Wesselinova, D.; Tsenov, J. A. Eur. J. Med. Chem. 2016, 123, 75.
10. [10]
  Guo, Y. C.; Li, J.; Ma, J. L.; Yu, Z. R.; Wang, H. W.; Zhu, W. J.; Liao, X. C.; Zhao, Y. F. Chin. Chem. Lett. 2015, 26, 757.
11. [11]
  Song, X. J.; Yang, P.; Gao, H.; Wang, Y.; Dong, X. G.; Tan, X. H. Chin. Chem. Lett. 2014, 25, 1007.
12. [12]
  Mavrova, A. T.; Vuchev, D.; Anichina, K.; Vassilev, N. Eur. J. Med. Chem. 2010, 45, 5857.
13. [13]
  Fruscia, P. D.; Zacharioudakis, E.; Liu, C.; Moniot, S.; Laohasinnarong, S.; Khongkow, M.; Harrison, L. M.; Koltsida, M.; Reynolds, C. R.; Schmidtkunz, K.; Jung, M.; Chapman, K. L.; Steegborn, C.; Dexter, D. T.; Sternberg, M. J. E.; Lam, E. W. F.; Fuchter, M. J. ChemMedChem 2015, 10, 76.
14. [14]
  Zhao, A. L.; Liu, S.; Zhu, Y. M.; Wang, T.; Luo, J. Chin. J. Org. Chem. 2017, 37, 1879 (in Chinese).
15. [15]
  Miwa, K.; Hitaka, T.; Imada, T.; Sasaki, S.; Yoshimatsu, M.; Kusaka, M.; Tanaka, A.; Nakata, D.; Furuya, S.; Endo, S.; Hamamura, K.; Kitazaki, T. J. Med. Chem. 2011, 54, 4999.
16. [16]
  Markham, A. Drugs 2019, 79, 676.
17. [17]
  Porvasnik, S. L.; Germain, S.; Embury, J.; Gannon, K. S.; Jacques, V.; Murray, J.; Byrne, B. J.; Shacham, S.; Al-Mousily, F. J. Pharm. Exp. Ther. 2010, 334, 365.
18. [18]
  Svejda, B.; Kidd, M.; Giovinazzo, F.; Eltawil, K.; Gustafsson, B. I.; Pfragner, R.; Modlin, I. M. Cancer 2010, 116, 2905.
19. [19]
  Wu, Y. L.; Yoshida, M.; Emoto, H.; Ishii, H.; Koga, K.; Tanaka, M. Jpn. J. Pharmacol. 2000, 83, 32.
20. [20]
  Schreiber, S.; Schreiber, F.; Lockhart, S. N.; Horng, A.; Bejanin, A.; Landau, S. M.; Jagust, W. J. JAMA Neurol. 2017, 20, 3.
21. [21]
  Beggs, J. E.; Tian, S.; Jones, G. G.; Xie, J.; Iadevaia, V.; Jenei, V.; Thomas, G.; Proud, C. G. Biochem. J. 2015, 467, 66.
22. [22]
  Jin, X.; Merrett, J. E.; Tong, S.; Flower, B.; Xie, J.; Yu, R.; Tian, S.; Gao, L.; Zhao, J.; Wang, X.; Jiang, T.; Proud, C. G. Eur. J. Med. Chem. 2019, 162, 737.
23. [23]
  Wang, Y. D.; Johnson, S. M.; Powell, D.; Mcginnis, J. P.; Miranda, M.; Rabindran, S. K. Bioorg. Med. Chem. Lett. 2005, 15, 3764.
24. [24]
  Ouyang, L.; Zhang, L.; Liu, J.; Fu, L.; Yao, D.; Zhao, Y.; Zhang, S.; Wang, G.; He, G.; Liu, B. J. Med. Chem. 2017, 60, 9991.
25. [25]
  Yang, P.; Wang, Y.; Duan, Z. C.; Shao, Y.; Nie, G. H.; Song, X. J.; Tian, D. T. Chin. J. Struct. Chem. 2013, 32, 1024.
26. [26]
  Gao, H.; Fu, J.; Zhao, M. J.; Song, X. J.; Yang, P.; Zhang, Y. Chin. J. Struct. Chem. 2015, 34, 10
27. [27]
  Huang, Y.; Dömling, A. Mol. Diversity 2011, 15, 4.
28. [28]
  Zhang, B. Z.; Liu, Y.; Wang, L. Chin. J. Antibiot. 2012, 37, 579 (in Chinese).
29. [29]
  Li, M. R.; Ding, Q. F.; Li, B. Y.; Yu, Y.; Huang, H.; Huang, F. Chin. J. Org. Chem. 2019, 39, 2714 (in Chinese).
30. [30]
  Wang, Z. H.; Wang, L.; Wang, Z. M.; Li, P. H. Asian J. Org. Chem. 2019, 8, 3. doi: 10.1002/ajoc.201800689
31. [31]
  Jing, X.; Li, Z.; Wu, L.; Yan, C. J. Iran. Chem. Soc. 2011, 8, 112.
32. [32]
  Fruscia, P. D.; Zacharioudakis, E.; Liu, C.; Moniot, S.; Laohasinnarong, S.; Khongkow, M.; Harrison, L. F.; Koltsida, K.; Reynolds, C. R.; Schmidtkunz, K.; Jung, M.; Chapman, K. L.; Steegborn, C.; Dexter, D. Y.; Sternberg, M. J. E.; Lam, E. W. F.; Fuchter, M. J. ChemMedChem 2015, 10, 70.
33. [33]
  Han, F. B.; Lin, S. W.; Liu, P.; Liu, X. J.; Tao, J.; Deng, X. B.; Yi, C. Q.; Xu, H. ACS Med. Chem. Lett. 2015, 6, 436.
34. [34]
  Gill, K. R.; Kumar, V.; Bishnoi, M.; Yadav, K.; Kondepudi, K. K.; Bariwal, J. Anti-Cancer Agents Med. Chem. 2017, 17, 706.
35. [35]
  Pokhodylo, N. T.; Matiychuk, V. S.; Obushak, M. D. Tetrahedron 2008, 64, 1431.
36. [36]
  Pokhodylo, N. T.; Shyyka, O. Y.; Matiychuk, V. S.; Obushak, M. D. ACS Comb. Sci. 2015, 17, 399. doi: 10.1021/co5001376
37. [37]
  Soares, M. I.; Lyra, A. C. F.; Henriques, M. S. C.; PaixŃo, J. A.; Melo, T. M. V. D. P. Tetrahedron 2015, 71, 3344.
38. [38]
  Moustafa, A. H.; Ahmed, W. W.; Khodairy, A. J. Heterocycl. Chem. 2017, 54, 3493.
39. [39]
  Hassan, A. A.; Khattab, R. R.; Wasfy, A. A. F.; Abuzeid, K. M.; Hassan, N. A. J. Heterocycl. Chem. 2018, 55, 908.
40. [40]
  Fouad, M. M.; El-Bendary, E. R.; Suddek, G. M.; Shehata, I. A.; El-Kerdawy, M. M. Bioorg. Chem. 2018, 81, 588.
41. [41]
  Ameen, M. A.; Ahmed, E. K.; Mahmoud, H. I.; Ramadan, M. J. Heterocycl. Chem. 2019, 56, 1832.
42. [42]
  Mavrova, A. T.; Vuchev, D.; Anichina, K.; Vassilev, N. Eur. J. Med. Chem. 2010, 45, 5858.
43. [43]
  Dai, Z. X.; Chen, H.; Liu, M. G.; Ding, M. W. Heterocycl. Commun. 2011, 17, 198.
44. [44]
  El-Shehry, M. F.; Hosni, H. M.; Amr, A. E.; Ibrahim, A. A.; Fayed, A. A.; Elnaggar, D. H. Russ. J. Gen. Chem. 2019, 89, 1529.
45. [45]
  Bakavoli, M.; Bagherzadeh, G.; Vaseghifar, M.; Shiri, A.; Pordeli, P. J. Chem. Res. 2009, 654.
46. [46]
  Yang, P.; Wang, Y.; Duan, Z. C.; Shao, Y.; Nie, G. H.; Song, X. J.; Tian, D. T. Chin. J. Struct. Chem. 2013, 32, 1024.
47. [47]
  Furuyama, T.; Noguchi, D.; Suzuki, Y.; Kobayashi, N. Can. J. Chem. 2014, 92, 767.
48. [48]
  Gao, H.; Fu, J.; Zhao, M. J.; Song, X. J.; Yang, P.; Zhang, Y. Chin. J. Struct. Chem. 2015, 34, 10.
49. [49]
  Atapour-Mashhad, H.; Soukhtanloo, M.; Massoudi, A.; Shiri, A.; Parizadeh, S. M.; Bakavoli, M. J. Heterocycl. Chem. 2017, 54, 367.
50. [50]
  Sureja, D. K.; Vadalia, K. R. J. Saudi Chem. Soc. 2017, 22, 251.
51. [51]
  Khatri, T. T.; Shah, V. H. J. Chil. Chem. Soc. 2017, 62, 3355.
52. [52]
  Ramya, P. V. S.; Thatikonda, S.; Angapelly, S.; Babu, B. N.; Naidu, V. G. M.; Kamal, A. ChemistrySelect 2018, 3, 3102.
53. [53]
  Zong, C. Y.; Zhang, L. J.; Gu, M. Y.; Sun, Y. Q. Chin. J. Org. Chem. 2018, 38, 1422 (in Chinese).
54. [54]
  Elmetwally, S. A.; Saied, K. F.; Eissa, I. H.; Elkaeed, E. B. Bioorg. Chem. 2019, 88, 102944. doi: 10.1016/j.bioorg.2019.102944
55. [55]
  Han, Q.; Yin, Z. J.; Sui, J. J.; Wang, Q. M.; Sun, Y. Q. J. Braz. Chem. Soc. 2019, 30, 1487.
56. [56]
  Poojari, S.; Naik, P. P.; Krishnamurthy, G. Tetrahedron Lett. 2012, 53, 4639. doi: 10.1016/j.tetlet.2012.06.017
57. [57]
  El-Sayed, N. N.; Abdelaziz, M. A.; Wardakhan, W. W.; Mohareb, R. M. Steroids 2016, 107, 99.
58. [58]
  Amawi, H.; Karthikeyan, C.; Pathak, R.; Hussein, N.; Christman, R.; Robey, R.; Ashby Jr. C. R.; Trivedi, P.; Tiwari, A. K. Eur. J. Med. Chem. 2017, 138, 1058.
59. [59]
  Ghashang, M. J. Iran. Chem. Soc. 2018, 15, 56.
60. [60]
  Ghayour, F.; Shafiee, M. R. M.; Ghashang, M. Main Group Met. Chem. 2018, 41, 23.
61. [61]
  Shafighi, S.; Shafiee, M. R. M.; Ghashang, M. J. Sulfur Chem. 2018, 39, 404.
62. [62]
  Brough, P. A.; Barril, X.; Borgognoni, J.; Chene, P.; Davies, N. G. M.; Davis, B.; Drysdale, M. J.; Dymock, B.; Eccles, S. A.; Garcia-Echeverria, C.; Fromont, C.; Hayes, A.; Hubbard, R. E.; Jordan, A. M.; Jensen, M. R.; Massey, A.; Merrett, A.; Padfield, A.; Parsons, R.; Radimerski, T.; Raynaud, F. I.; Robertson, A.; Roughley, S. D.; Schoepfer, J.; Simmonite, H.; Sharp, S. Y.; Surgenor, A.; Valenti, M.; Walls, S.; Webb, P.; Wood, M.; Workman, P.; Wright, L. J. Med. Chem. 2009, 52, 4796.
63. [63]
  Kobayashi, K.; Suzuki, T.; Kozuki, T.; Matsumoto, N.; Hiyoshi, H.; Umezu, K. Heterocycles 2012, 85, 1407.
64. [64]
  Wilding, B.; Faschauner, S.; Klempier, N. Tetrahedron Lett. 2015, 56, 4487.
65. [65]
  Tolba, M. S.; El-Dean, A. M. K.; Ahmed, M.; Hassanien, R.; Farouk, M. ARKIVOC 2017, 5, 231.
66. [66]
  Ho, Y. W.; Yao, W. H. J. Chem. 2013, 2013, 5.
67. [67]
  Xu, J.; Fan, W. G.; Popowycz, F.; Queneau, Y.; Gu, Y. L. Chin. J. Org. Chem. 2019, 39, 2131 (in Chinese).
68. [68]
  Tang, M.; Xing, D.; Cai, M. Q.; Hu, W. H. Chin. J. Org. Chem. 2014, 34, 1268 (in Chinese).
69. [69]
  Kusebauch, U.; Beck, B.; Messer, K.; Herdtweck, E.; Domling, A. Org. Lett. 2003, 5, 4021. doi: 10.1021/ol035010u
70. [70]
  Shi, T.; Kaneko, L.; Sandino, M.; Busse, R.; Zhang, M.; Mason, D.; Machulis, J.; Ambrose, A. J.; Zhang, D. D.; Chapman, E. ACS Sustain. Chem. Eng. 2018, 7, 1526.
71. [71]
  Shi, T.; Zerio, C.; Sivinski, J.; Ambrose, A. J.; Moore, K. T.; Buckley, T.; Kaneko, L.; Zhang, M.; Zhang, D. D.; Chapman, E. Eur. J. Org. Chem. 2019, 3270.
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