REVIEWS

Recent Progress in the Synthesis of Thiazole-Containing Compounds

  • Yafang Zhang ,
  • Xuan Huang ,
  • Qi Lin ,
  • Haiqiong Zhong ,
  • Zhiqiang Weng ,
  • Wei Wu
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  • a College of Materials and Chemical Engineering, Minjiang University, Fuzhou 350108
    b Fujian Engineering Research Center of New Chinese Lacquer Materials, Minjiang University, Fuzhou 350108
    c Fujian Provincial University Engineering Research Center of Green Materials and Chemical Engineering, Minjiang University, Fuzhou 350108

Received date: 2023-10-07

  Revised date: 2023-11-26

  Online published: 2023-12-21

Supported by

National Natural Science Foundation of China(22171124); National Natural Science Foundation of China(22301118); Natural Science Foundation of Fujian Province(2022J05233); Minjiang University(MJY21041)

Abstract

Thiazole is a five-membered aromatic heterocycle containing nitrogen and sulfur heteroatoms, which is widely found in drugs, natural products and functional materials. So far, there have been many reports on the synthesis of thiazole compounds. This review focuses on the synthetic methods for the preparation of thiazole rings and the scope of application of these synthetic methods, which can be used as a reference for other researchers to efficiently synthesize and apply thiazole compounds.

Cite this article

Yafang Zhang , Xuan Huang , Qi Lin , Haiqiong Zhong , Zhiqiang Weng , Wei Wu . Recent Progress in the Synthesis of Thiazole-Containing Compounds[J]. Chinese Journal of Organic Chemistry, 2024 , 44(5) : 1458 -1479 . DOI: 10.6023/cjoc202310007

References

[1]
Khatik, L. G.; Datusalia, K. A.; Ahsan, W.; Kaur, P.; Vyas, M.; Mittal, A.; Nayak, K. S. Curr. Drug Discovery Technol. 2018, 15, 163.
[2]
Shahin, I. G.; Abutaleb, N. S.; Alhashimi, M.; Kassab, A. E.; Mohamed, K. O.; Taher, A. T.; Seleem, M. N.; Mayhoub, A. S. Eur. J. Med. Chem. 2020, 202, 112497.
[3]
Makam, P.; Kankanala, R.; Prakash, A.; Kannan, T. Eur. J. Med. Chem. 2013, 69, 564.
[4]
Reddy, G. M.; Garcia, J. R.; Reddy, V. H.; de Andrade, A. M.; Camilo, A.; Pontes Ribeiro, R. A.; de Lazaro, S. R. Eur. J. Med. Chem. 2016, 123, 508.
[5]
Li, M.; Xia, D.-G.; Wang, Y.-X.; Cheng, X.; Gong, J.-X.; Chen, Y.; Lü, X.-H. Chin. J. Org. Chem. 2023, 43, 686 (in Chinese).
[5]
( 李猛, 夏东国, 王云霄, 程祥, 巩杰秀, 陈耀, 吕献海, 有机化学, 2023, 43, 686.)
[6]
Dawood, K. M.; Eldebss, T. M. A.; El-Zahabi, H. S. A.; Yousef, M. H. Eur. J. Med. Chem. 2015, 102, 266.
[7]
Helal, M. H. M.; Salem, M. A.; El-Gaby, M. S. A.; Aljahdali, M. Eur. J. Med. Chem. 2013, 65, 517.
[8]
Abbas, E. M. H.; Gomha, S. M.; Farghaly, T. A.; Abdalla, M. M. Curr. Org. Synth. 2016, 13, 456.
[9]
Zhao, X. J.; Chen, X. H. Chin. J. Pharm. 2006, 37, 441 (in Chinese).
[9]
( 赵晓娟; 陈学恒, 中国医药工业杂志, 2006, 37, 441.)
[10]
Hutchinson, I.; Bradshaw, T. D.; Matthews, C. S.; Stevens, M. F. G.; Westwell, A. D. Bioorg. Med. Chem. Lett. 2003, 13, 471.
[11]
Chen, B.-C.; Zhao, R.; Wang, B.; Droghini, R.; Lajeunesse, J.; Sirard, P.; Endo, M.; Balasubramanian, B.; Barrish, J. C. ARKIVOC 2009, 32.
[12]
Cai, W.-X.; Liu, A.-L.; Li, Z.-M.; Dong, W.-L.; Liu, X.-H.; Sun, N.-B. Appl. Sci. 2016, 6, 8.
[13]
Jeankumar, V. U.; Renuka, J.; Santosh, P.; Soni, V.; Sridevi, J. P.; Suryadevara, P.; Yogeeswari, P.; Sriram, D. Eur. J. Med. Chem. 2013, 70, 143.
[14]
Yang, Z.-H.; Chen, A.-Y.; Hu, A.-X.; Ye, J. Chin. J. Org. Chem. 2017, 37, 149 (in Chinese).
[14]
( 杨子辉, 陈爱羽, 胡艾希, 叶姣, 有机化学, 2017, 37, 149.)
[15]
Chen, S.; Shao, Y.-Y.; Fu, X.-H.; Chen, Q.-W.; Du, X.-H.; Tan, C.-X. Chin. J. Org. Chem. 2022, 42, 3870 (in Chinese).
[15]
( 陈澍, 邵莹莹, 付欣豪, 陈庆悟, 杜晓华, 谭成侠, 有机化学, 2022, 42, 3870.)
[16]
Cui, S. F.; Wang, Y.; Lv, J. S.; Damu, G. L. V.; Zhou, C. H. Sci. China Chem. 2012, 42, 1105 (in Chinese).
[16]
( 崔胜峰, 王艳, 吕敬松, DAMU, Guri L. V., 周成合, 中国科学: 化学, 2012, 42, 1105.)
[17]
Ji, M.; Dong, C.; Guo, Q.; Du, M.; Guo, Q.; Sun, X.; Wang, E.; Zhou, E. Macromol. Rapid Commun. 2023, 44, 2300102.
[18]
Yang, K.; Chen, Z.; Wang, Y.; Guo, X. Acc. Mater. Res. 2023, 4, 237.
[19]
Hantzsch, A.; Weber, J. H. Ber. Dtsch. Chem. Ges. 1887, 20, 3118.
[20]
Sahil; Kaur, K.; Jaitak, V. Curr. Med. Chem. 2022, 29, 4958.
[21]
Duc, X. D.; Chung, T. N. Curr. Org. Synth. 2022, 19, 702.
[22]
Niu, Z.-X.; Wang, Y.-T.; Zhang, S.-N.; Li, Y.; Chen, X.-B.; Wang, S.-Q.; Liu, H.-M. Eur. J. Med. Chem. 2023, 250, 115172.
[23]
Shahin, G. I.; Mohamed, O. K.; Taher, T. A.; Mayhoub, S. A.; Kassab, E. A. Mini-Rev. Org. Chem. 2023, 20, 270.
[24]
Sharma, S.; Devgun, M.; Narang, R.; Lal, S.; Rana, A. C. Indian J. Pharm. Educ. Res. 2022, 56, 646.
[25]
Goff, D.; Fernandez, J. Tetrahedron Lett. 1999, 40, 423.
[26]
Miller, T. J.; Farquar, H. D.; Sheybani, A.; Tallini, C. E.; Saurage, A. S.; Fronczek, F. R.; Hammer, R. P. Org. Lett. 2002, 4, 877.
[27]
Ueno, M.; Togo, H. Synthesis 2004, 2004, 2673.
[28]
Narender, M.; Reddy, M. S.; Sridhar, R.; Nageswar, Y. V. D.; Rao, K. R. Tetrahedron Lett. 2005, 46, 5953.
[29]
Das, B.; Saidi Reddy, V.; Ramu, R. J. Mol. Catal. A: Chem. 2006, 252, 235.
[30]
Noei, J.; Khosropour, A. R. Ultrason. Sonochem. 2009, 16, 711.
[31]
Li, Y.; Ma, L.-F.; Wang, X.-J.; Lei, B.-W.; Zhao, Y.; Yang, J.-Y.; Li, Z.-Y. Chin. J. Org. Chem. 2017, 37, 1213 (in Chinese).
[31]
( 李瑶, 马丽芳, 王晓姣, 雷搏文, 赵怡, 杨嘉宇, 李子元, 有机化学, 2017, 37, 1213.)
[32]
Heravi, M. M.; Poormohammad, N.; Beheshtiha, Y. S.; Baghernejad, B. Synth. Commun. 2011, 41, 579.
[33]
Gao, W.-T.; Lan, S.; Zheng, H.-M.; Bairenqing, Z.-M. Chin. J. Org. Chem. 2015, 35, 144 (in Chinese).
[33]
( 高文涛, 兰帅, 郑宏梅, 白仁青卓玛, 有机化学, 2015, 35, 144.)
[34]
Arunkumar, K.; Naresh Kumar Reddy, D.; Chandrasekhar, K. B.; Rajender Kumar, P.; Shiva Kumar, K.; Pal, M. Tetrahedron Lett. 2012, 53, 3885.
[35]
Xiao, J.; Li, W.; Zhou, X.-Q.; Liu, D.-Z. Chem. Ind. Eng. 2011, 28, 30 (in Chinese).
[35]
( 肖捷, 李巍, 周雪琴, 刘东志, 化学工业与工程, 2011, 28, 30.)
[36]
Kesari, C.; Rama, K. R.; Sedighi, K.; Stenvang, J.; Bj?rkling, F.; Kankala, S.; Thota, N. Synth. Commun. 2021, 51, 1406.
[37]
Azizi, N.; Rahimi, Z.; Alipour, M. C. R. Chim. 2015, 18, 626.
[38]
Ziyaei Halimehjani, A.; Hasani, L.; Ali Alaei, M.; Saidi, M. R. Tetrahedron Lett. 2016, 57, 883.
[39]
Zhang, X.; Teo, W. T.; Sally; Chan, P. W. H. J. Org. Chem. 2010, 75, 6290.
[40]
Wu, G.-D.; Wang, X.-L.; Zhang, L.-M.; Zhang, F.; Liu, X.-F.; Liu, C.-R. Chin. J. Org. Chem. 2015, 35, 2537 (in Chinese).
[40]
( 吴功德, 王晓丽, Liming Zhang, 张方, 刘献锋, 刘从容, 有机化学, 2015, 35, 2537.)
[41]
Obijalska, E.; B?aszczyk, M.; Kowalski, M. K.; Mlostoń, G.; Heimgartner, H. J. Fluorine Chem. 2019, 220, 35.
[42]
Shaterian, H. R.; Molaei, P. Appl. Organomet. Chem. 2019, 33, e4964.
[43]
Narender, M.; Somi Reddy, M.; Kumar, V. P.; Srinivas, B.; Sridhar, R.; Nageswar, Y. V. D.; Rao, K. R. Synthesis 2007, 2007, 3469.
[44]
Kuarm, B. S.; Madhav, J. V.; Rajitha, B.; Rajitha, B. Lett. Org. Chem. 2011, 8, 549.
[45]
Vekariya, R. H.; Patel, K. D.; Vekariya, M. K.; Prajapati, N. P.; Rajani, D. P.; Rajani, S. D.; Patel, H. D. Res. Chem. Intermed. 2017, 43, 6207.
[46]
Zheng, R.; Hu, X.; Jiang, H.; Guo, H.; Wang, L. Synthesis 2023, 55, 2091.
[47]
Yadav, J. S.; Reddy, B. V. S.; Rao, Y. G.; Narsaiah, A. V. Tetrahedron Lett. 2008, 49, 2381.
[48]
Babu, B. H.; Vijay, K.; Murali Krishna, K. B.; Sharmila, N.; Ramana, M. B. J. Chem. Sci. 2016, 128, 1475.
[49]
Lin, P.-Y.; Hou, R.-S.; Wang, H.-M.; Kang, I.-J.; Chen, L.-C. J. Chin. Chem. Soc. 2009, 56, 455.
[50]
Meshram, H. M.; Kumar, D. A.; Vara Prasad, B. R. Synth. Commun. 2009, 39, 2317.
[51]
Qin, X.; Yu, H. B.; Dai, H.; Qin, Z. F.; Zhang, X.; Bing, G. F.; Wang, T. T.; Fang, J. X. Chin. Chem. Lett. 2010, 21, 283.
[52]
Zhao, X.; Geng, Q.-F.; Zhou, T.-H.; Gao, X.-H.; Liu, G. Chin. Chem. Lett. 2013, 24, 31.
[53]
Chen, Y.; Lv, S.; Lai, R.; Xu, Y.; Huang, X.; Li, J.; Lv, G.; Wu, Y. Chin. Chem. Lett. 2021, 32, 2555.
[54]
Zhu, Y.-P.; Yuan, J.-J.; Zhao, Q.; Lian, M.; Gao, Q.-H.; Liu, M.-C.; Yang, Y.; Wu, A.-X. Tetrahedron 2012, 68, 173.
[55]
Xue, W.-J.; Zheng, K.-L.; Li, H.-Z.; Gao, F.-F.; Wu, A.-X. Tetrahedron Lett. 2014, 55, 4212.
[56]
Ghodse, S. M.; Telvekar, V. N. Tetrahedron Lett. 2015, 56, 472.
[57]
Safari, J.; Abedi-Jazini, Z.; Zarnegar, Z.; Sadeghi, M. Catal. Commun. 2016, 77, 108.
[58]
Madhav, B.; Narayana Murthy, S.; Anil Kumar, B. S. P.; Ramesh, K.; Nageswar, Y. V. D. Tetrahedron Lett. 2012, 53, 3835.
[59]
Aggarwal, R.; Kumar, S.; Singh, S. P. J. Sulfur Chem. 2012, 33, 521.
[60]
Ablajan, K.; Liju, W.; Tuoheti, A. Lett. Org. Chem. 2013, 10, 715.
[61]
de Moraes Gomes, P. A. T.; de Oliveira Barbosa, M.; Farias Santiago, E.; de Oliveira Cardoso, M. V.; Capistrano Costa, N. T.; Hernandes, M. Z.; Moreira, D. R. M.; da Silva, A. C.; dos Santos, T. A. R.; Pereira, V. R. A.; Brayner dos Santosd, F. A.; do Nascimento Pereira, G. A.; Ferreira, R. S.; Leite, A. C. L. Eur. J. Med. Chem. 2016, 121, 387.
[62]
Nikpassand, M.; Zare Fekri, L.; Sanagou, S. Dyes Pigm. 2017, 136, 140.
[63]
Mekky, A. E. M.; Sanad, S. M. H.; El-Idreesy, T. T. Synth. Commun. 2021, 51, 3332.
[64]
Khanoussi, S.; Benmohammed, A.; Khoumeri, O.; Kadiri, M.; Djafri, A.; Terme, T.; Vanelle, P. Lett. Org. Chem. 2023, 20, 11.
[65]
Alqahtani, A. M.; Bayazeed, A. A. Arab. J. Chem. 2021, 14, 102914.
[66]
Brandsma, L.; De Jong, R. L. P.; Verkruijsse, H. D. Synthesis 1985, 1985, 948.
[67]
Kodomari, M.; Aoyama, T.; Suzuki, Y. Tetrahedron Lett. 2002, 43, 1717.
[68]
Aoyama, T.; Murata, S.; Arai, I.; Araki, N.; Takido, T.; Suzuki, Y.; Kodomari, M. Tetrahedron 2006, 62, 3201.
[69]
Khidre, R. E.; Radini, I. A. M. Sci. Rep. 2021, 11, 7846.
[70]
Yang, H.; Chen, Y.; Xu, X.; Li, Z. Synlett 2022, 34, 176.
[71]
Banert, K.; Al-Hourani, B. J.; Groth, S.; Vrobel, K. Synthesis 2005, 2005, 2920.
[72]
Sasmal, P. K.; Chandrasekhar, A.; Sridhar, S.; Iqbal, J. Tetrahedron 2008, 64, 11074.
[73]
Yavari, I.; Amirahmadi, A.; Halvagar, M. R. Synlett 2017, 28, 2629.
[74]
Guo, W.; Zhao, M.; Tan, W.; Zheng, L.; Tao, K.; Chen, L.; Wang, M.; Chen, D.; Fan, X. Asian J. Org. Chem. 2018, 7, 1893.
[75]
Lingaraju, G. S.; Swaroop, T. R.; Vinayaka, A. C.; Sharath Kumar, K. S.; Sadashiva, M. P.; Rangappa, K. S. Synthesis 2012, 44, 1373.
[76]
Rajeev, N.; Swaroop, T. R.; Anil, S. M.; Bommegowda, Y. K.; Rangappa, K. S.; Sadashiva, M. P. Synlett 2017, 28, 2281.
[77]
Kiran, K. R.; Swaroop, T. R.; Rajeev, N.; Anil, S. M.; Rangappa, K. S.; Sadashiva, M. P. Synthesis 2020, 52, 1444.
[78]
Miura, T.; Funakoshi, Y.; Fujimoto, Y.; Nakahashi, J.; Murakami, M. Org. Lett. 2015, 17, 2454.
[79]
Sheldrake, P. W.; Matteucci, M.; McDonald, E. Synlett 2006, 2006, 460.
[80]
Bao, X.-F.; Qiao, X.-J.; Hou, X.; Fang, W.-H.; Liu, X.-L.; Chen, G.-L. J. Braz. Chem. Soc. 2016, 27, 2388.
[81]
Sanz-Cervera, J. F.; Blasco, R.; Piera, J.; Cynamon, M.; Ibá?ez, I.; Murguía, M.; Fustero, S. J. Org. Chem. 2009, 74, 8988.
[82]
Kumar, S. V.; Parameshwarappa, G.; Ila, H. J. Org. Chem. 2013, 78, 7362.
[83]
Wu, M.; Jiang, Y.; An, Z.; Qi, Z.; Yan, R. Adv. Synth. Catal. 2018, 360, 4236.
[84]
Wang, X.; Qiu, X.; Wei, J.; Liu, J.; Song, S.; Wang, W.; Jiao, N. Org. Lett. 2018, 20, 2632.
[85]
Jiang, J.; Huang, H.; Deng, G.-J. Green Chem. 2019, 21, 986.
[86]
Chen, L.; Xuchen, X.; Wang, F.; Yang, Y.; Deng, G.; Liu, Y.; Liang, Y. Org. Biomol. Chem. 2021, 19, 10068.
[87]
Kim, D.; Baek, D. J.; Lee, D.; Liu, K.-H.; Bae, J.-S.; Gong, Y.-D.; Min, K. H.; Lee, T. Tetrahedron 2015, 71, 3367.
[88]
Yao, Y.; Lin, B.; Wu, M.; Zhang, Y.; Huang, Y.; Han, X.; Weng, Z. Org. Biomol. Chem. 2022, 20, 8761.
[89]
Pavlik, J. W.; Pandit, C. R.; Samuel, C. J.; Day, A. C. J. Org. Chem. 1993, 58, 3407.
[90]
Carradori, S.; Rotili, D.; De Monte, C.; Lenoci, A.; D'Ascenzio, M.; Rodriguez, V.; Filetici, P.; Miceli, M.; Nebbioso, A.; Altucci, L.; Secci, D.; Mai, A. Eur. J. Med. Chem. 2014, 80, 569.
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