SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 9: 2626 - 2640

DOI: https://doi.org/10.6023/cjoc202004002

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

  • Sun Xiaohua ,
  • Sun Chuance ,
  • Feng Lijun ,
  • Kang Congmin
Expand
  • College of Chemical Engineering, Qingdao University of Science and Technology, Shandong Province, Qingdao, Shandong 266042

Received date: 2020-04-01

  Revised date: 2020-05-31

  Online published: 2020-06-19

Supported by

Project supported by the National Natural Science Foundation of China (No. 21272131).

Fold

Abstract

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.

Key words： thieno[2,3-d]pyrimidine; tandem cyclization; microwave reaction; one-pot multi-component reaction

Cite this article

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

References

[1] Hafez, H. N.; El-gazzar, A. B. A.; Nawwar, G. A. M. Eur. J. Med. Chem. 2010, 45, 1486.
[2] Ashalatha, B. V.; Narayana, B.; Raj, K. K. V.; Kumari, N. S. Eur. J. Med. Chem. 2007, 42, 722.
[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] Al-Taisan, K. M.; Al-Hazimi, H.; Al-Shihry, S. S. Molecules 2010, 15, 3939.
[5] El-Batanony, N. H. Period. Biol. 2017, 119, 29.
[6] Bakavoli, M.; Bagherzadeh, G.; Vaseghifar, M.; Shiri, A.; Pordeli, P. J. Chem. Res. 2009, 654.
[7] Kotaiah, Y.; Harikrishna, N.; Nagaraju, K.; Rao, C. V. Eur. J. Med. Chem. 2012, 58, 341.
[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] Mavrova, A. T.; Dimov, S.; Yancheva, D.; Rangelov, M.; Wesselinova, D.; Tsenov, J. A. Eur. J. Med. Chem. 2016, 123, 75.
[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] Song, X. J.; Yang, P.; Gao, H.; Wang, Y.; Dong, X. G.; Tan, X. H. Chin. Chem. Lett. 2014, 25, 1007.
[12] Mavrova, A. T.; Vuchev, D.; Anichina, K.; Vassilev, N. Eur. J. Med. Chem. 2010, 45, 5857.
[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] Zhao, A. L.; Liu, S.; Zhu, Y. M.; Wang, T.; Luo, J. Chin. J. Org. Chem. 2017, 37, 1879(in Chinese). (赵安林, 刘姝, 朱咏梅, 王涛, 罗劲, 有机化学, 2017, 37, 1879.)
[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] Markham, A. Drugs 2019, 79, 676.
[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] Svejda, B.; Kidd, M.; Giovinazzo, F.; Eltawil, K.; Gustafsson, B. I.; Pfragner, R.; Modlin, I. M. Cancer 2010, 116, 2905.
[19] Wu, Y. L.; Yoshida, M.; Emoto, H.; Ishii, H.; Koga, K.; Tanaka, M. Jpn. J. Pharmacol. 2000, 83, 32.
[20] Schreiber, S.; Schreiber, F.; Lockhart, S. N.; Horng, A.; Bejanin, A.; Landau, S. M.; Jagust, W. J. JAMA Neurol. 2017, 20, 3.
[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] 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] Wang, Y. D.; Johnson, S. M.; Powell, D.; Mcginnis, J. P.; Miranda, M.; Rabindran, S. K. Bioorg. Med. Chem. Lett. 2005, 15, 3764.
[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] 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] Gao, H.; Fu, J.; Zhao, M. J.; Song, X. J.; Yang, P.; Zhang, Y. Chin. J. Struct. Chem. 2015, 34, 10
[27] Huang, Y.; Dömling, A. Mol. Diversity 2011, 15, 4.
[28] Zhang, B. Z.; Liu, Y.; Wang, L. Chin. J. Antibiot. 2012, 37, 579(in Chinese). (张豹子, 刘洋, 王凌, 中国抗生素杂志, 2012, 37, 579.)
[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). (李明瑞, 丁奇峰, 李博洋, 于杨, 黄和, 黄飞, 有机化学, 2019, 39, 2714.)
[30] Wang, Z. H.; Wang, L.; Wang, Z. M.; Li, P. H. Asian J. Org. Chem. 2019, 8, 3.
[31] Jing, X.; Li, Z.; Wu, L.; Yan, C. J. Iran. Chem. Soc. 2011, 8, 112.
[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] 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] Gill, K. R.; Kumar, V.; Bishnoi, M.; Yadav, K.; Kondepudi, K. K.; Bariwal, J. Anti-Cancer Agents Med. Chem. 2017, 17, 706.
[35] Pokhodylo, N. T.; Matiychuk, V. S.; Obushak, M. D. Tetrahedron 2008, 64, 1431.
[36] Pokhodylo, N. T.; Shyyka, O. Y.; Matiychuk, V. S.; Obushak, M. D. ACS Comb. Sci. 2015, 17, 399.
[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] Moustafa, A. H.; Ahmed, W. W.; Khodairy, A. J. Heterocycl. Chem. 2017, 54, 3493.
[39] Hassan, A. A.; Khattab, R. R.; Wasfy, A. A. F.; Abuzeid, K. M.; Hassan, N. A. J. Heterocycl. Chem. 2018, 55, 908.
[40] Fouad, M. M.; El-Bendary, E. R.; Suddek, G. M.; Shehata, I. A.; El-Kerdawy, M. M. Bioorg. Chem. 2018, 81, 588.
[41] Ameen, M. A.; Ahmed, E. K.; Mahmoud, H. I.; Ramadan, M. J. Heterocycl. Chem. 2019, 56, 1832.
[42] Mavrova, A. T.; Vuchev, D.; Anichina, K.; Vassilev, N. Eur. J. Med. Chem. 2010, 45, 5858.
[43] Dai, Z. X.; Chen, H.; Liu, M. G.; Ding, M. W. Heterocycl. Commun. 2011, 17, 198.
[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] Bakavoli, M.; Bagherzadeh, G.; Vaseghifar, M.; Shiri, A.; Pordeli, P. J. Chem. Res. 2009, 654.
[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] Furuyama, T.; Noguchi, D.; Suzuki, Y.; Kobayashi, N. Can. J. Chem. 2014, 92, 767.
[48] Gao, H.; Fu, J.; Zhao, M. J.; Song, X. J.; Yang, P.; Zhang, Y. Chin. J. Struct. Chem. 2015, 34, 10.
[49] Atapour-Mashhad, H.; Soukhtanloo, M.; Massoudi, A.; Shiri, A.; Parizadeh, S. M.; Bakavoli, M. J. Heterocycl. Chem. 2017, 54, 367.
[50] Sureja, D. K.; Vadalia, K. R. J. Saudi Chem. Soc. 2017, 22, 251.
[51] Khatri, T. T.; Shah, V. H. J. Chil. Chem. Soc. 2017, 62, 3355.
[52] Ramya, P. V. S.; Thatikonda, S.; Angapelly, S.; Babu, B. N.; Naidu, V. G. M.; Kamal, A. ChemistrySelect 2018, 3, 3102.
[53] Zong, C. Y.; Zhang, L. J.; Gu, M. Y.; Sun, Y. Q. Chin. J. Org. Chem. 2018, 38, 1422(in Chinese). (纵朝阳, 张立洁, 顾梦婷, 孙雅泉, 有机化学, 2018, 38, 1422.)
[54] Elmetwally, S. A.; Saied, K. F.; Eissa, I. H.; Elkaeed, E. B. Bioorg. Chem. 2019, 88, 102944.
[55] Han, Q.; Yin, Z. J.; Sui, J. J.; Wang, Q. M.; Sun, Y. Q. J. Braz. Chem. Soc. 2019, 30, 1487.
[56] Poojari, S.; Naik, P. P.; Krishnamurthy, G. Tetrahedron Lett. 2012, 53, 4639.
[57] El-Sayed, N. N.; Abdelaziz, M. A.; Wardakhan, W. W.; Mohareb, R. M. Steroids 2016, 107, 99.
[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] Ghashang, M. J. Iran. Chem. Soc. 2018, 15, 56.
[60] Ghayour, F.; Shafiee, M. R. M.; Ghashang, M. Main Group Met. Chem. 2018, 41, 23.
[61] Shafighi, S.; Shafiee, M. R. M.; Ghashang, M. J. Sulfur Chem. 2018, 39, 404.
[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] Kobayashi, K.; Suzuki, T.; Kozuki, T.; Matsumoto, N.; Hiyoshi, H.; Umezu, K. Heterocycles 2012, 85, 1407.
[64] Wilding, B.; Faschauner, S.; Klempier, N. Tetrahedron Lett. 2015, 56, 4487.
[65] Tolba, M. S.; El-Dean, A. M. K.; Ahmed, M.; Hassanien, R.; Farouk, M. ARKIVOC 2017, 5, 231.
[66] Ho, Y. W.; Yao, W. H. J. Chem. 2013, 2013, 5.
[67] Xu, J.; Fan, W. G.; Popowycz, F.; Queneau, Y.; Gu, Y. L. Chin. J. Org. Chem. 2019, 39, 2131(in Chinese). (徐静, 范维刚, 波波维奇·弗洛伦斯, 葛诺伊夫, 顾彦龙, 有机化学, 2019, 39, 2131.)
[68] Tang, M.; Xing, D.; Cai, M. Q.; Hu, W. H. Chin. J. Org. Chem. 2014, 34, 1268(in Chinese). (唐敏, 邢栋, 蔡茂强, 胡文浩, 有机化学, 2014, 34, 1268.)
[69] Kusebauch, U.; Beck, B.; Messer, K.; Herdtweck, E.; Domling, A. Org. Lett. 2003, 5, 4021.
[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] 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.
Options
Outlines

/

〈 〉