Recent Progress in the Synthesis of Thiazole-Containing Compounds

doi:10.6023/cjoc202310007

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.

Key words: thiazole, five-membered heteroarene, synthetic method, application

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.

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Fig. & Tab. 55

Scheme 1. Method for the synthesis of 2,4-disubstituted thiazoles

Scheme 2. Hammer’s strategy for the synthesis of thiazoles

Scheme 3. Togo’s method for the synthesis of thiazoles

Scheme 4. Synthesis of thiazoles and 2-aminothiazoles catalyzed by β-cyclodextrin

Scheme 5. AMP-catalyzed synthesis of thiazoles

Scheme 6. Green method of ultrasound-promoted synthesis of thiazoles

Scheme 7. Synthesis of 2,4-disubstituted thiazoles by grinding method

Scheme 8. Synthetic method of thiazoles reported by Pal et al.

Scheme 9. Method of synthesizing thiazoles by Li and Thota et al.

Scheme 10. One-pot three-component reaction of 1,3-diketone, (thio) amide and NBS

Scheme 11. Method of synthesizing thiazoles by Dong and Garcia et al.

Scheme 12. Method for synthesis of 2-(alkylthio) thiazoles

Scheme 13. Cyclization reaction of alkynes with thioamides

Scheme 14. BF3?OEt2-promoted cyclization reaction of CF3CO- CHN2 and thioformamide/thiourea

Scheme 15. Fe3O4@vitamin B1-catalyzed synthesis of polysubstituted thiazole derivatives

Scheme 16. Synthesis of thiazoles and selenazoles ring from β-ketoesters and thio(seleno) urea catalyzed by β-cyclodextrin

Scheme 17. Synthesis of thiazoles and selenazoles from β-keto- esters and thio (seleno) urea catalyzed by xanthate sulfuric acid

Scheme 18. Microwave-assisted one-pot synthesis of thiazoles

Scheme 19. Visible-light-promoted cyclization reaction of active methylene ketones and thioureas

Scheme 20. Methods for the synthesis of 2-aminothiazoles reported by Yadav and Babu et al.

Scheme 21. Na2CO3-promoted synthesis of 2-aminothiazoles from α-(p-toluene)sulfonyloxy ketones with thiourea derivatives

Scheme 22. Condensation reaction of α-bromoketone with thiourea

Scheme 23. Rh2(OAc)4-catalyzed carbenoid insertion/annulation of sulfoxonium ylides with thioureas

Scheme 24. I2/CuO catalyzed one-pot tandem cyclization reaction

Scheme 25. I2-promoted tandem reaction of aryl methyl ketones, DMSO and thiourea

Scheme 26. NaICl2-catalyzed synthesis of 2-aminothiazoles

Scheme 27. Nanochitosan catalyzed one-pot reaction of ketones with thiourea or thiourea derivatives

Scheme 28. β-Cyclodextrin-catalyzed one-pot synthesis of thiazole/selenazole compounds

Scheme 29. Synthesis of thiazole-linked pyrazole compounds by grinding method

Scheme 30. Ablajan’s method for the synthesis of thiazoles

Scheme 31. Method for the synthesis of thiazoles reported by Kannan and Leite et al

Scheme 32. Fe3O4@SiO2@KIT-6-catalyzed synthesis of thiazole derivatives

Scheme 33. Piperazine-mediated one-pot three-component reaction of salicylaldehyde, semicarbazide and α-bromoketone

Scheme 34. Synthesis of non-substituted thiazole

Scheme 35. Synthesis of 2-aminothiazoles by KSCN/SiO2-RNH3OAc/Al2O3 system

Scheme 36. Method for the synthesis of thiazole derivatives by tandem reaction

Scheme 37. Metal-free synthesis of 2-aminothiazoles/lenazoles

Scheme 38. Cyclization reaction of allenyl isothiocyanate

Scheme 39. One-pot cyclization reaction of isothiocyanates and propargylamines

Scheme 40. Three-component tandem reaction of TMG, alkynoates and aryl isothiocyanates

Scheme 41. Alkali-promoted tandem cyclization of amidines, isothiocyanates and α-bromoesters/ketones

Scheme 42. A series of results on the synthesis of 4,5-disubstituted thiazoles by Rangappa et al.

Scheme 43. Tandem reaction of terminal alkynes, sulfonyl azides and thioesters

Scheme 44. Method for the synthesis of 5-arylthiazoles reported by Sheldrake et al.

Scheme 45. Synthesis of 5-(trifluoromethyl)-2-thiazolyl- amine

Scheme 46. Method of synthesis of thiazoles by Sanz-Cervera et al.

Scheme 47. Lawesson’s reagent-mediated one-step sulfidation-cyclization of enamides

Scheme 48. Iron-catalyzed cyclization reaction of enamines with sulfur

Scheme 49. Copper (II)-catalyzed three-component reaction of amines, aldehydes and sulfur

Scheme 50. Four-component one-pot tandem reaction of ketones, aldehydes, ammonium salts and sulfur

Scheme 51. Method of synthesis of 4-hydroxythiazole from amides and elemental sulfur

Scheme 52. Solid-phase synthesis of 2,4-disubstituted 5-carbamoyl-thiazole derivatives

Scheme 53. Synthesis of 2-trifluoromethylthiazole compounds by [3＋2] cycloaddition reaction

Scheme 54. Phototransposition process of isothiazole and thiazole

Figure 1. Summary and prospect of synthesis of thiazoles

References 90

[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).
	( 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.) doi: 10.6023/cjoc202206030
[6]	Dawood, K. M.; Eldebss, T. M. A.; El-Zahabi, H. S. A.; Yousef, M. H. Eur. J. Med. Chem. 2015, 102, 266. doi: 10.1016/j.ejmech.2015.08.005 pmid: 26291036
[7]	Helal, M. H. M.; Salem, M. A.; El-Gaby, M. S. A.; Aljahdali, M. Eur. J. Med. Chem. 2013, 65, 517. doi: 10.1016/j.ejmech.2013.04.005 pmid: 23787438
[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).
	( 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. pmid: 12565953
[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. doi: 10.1016/j.ejmech.2013.09.025 pmid: 24148991
[14]	Yang, Z.-H.; Chen, A.-Y.; Hu, A.-X.; Ye, J. Chin. J. Org. Chem. 2017, 37, 149 (in Chinese).
	( 杨子辉, 陈爱羽, 胡艾希, 叶姣, 有机化学, 2017, 37, 149.) doi: 10.6023/cjoc201607041
[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).
	( 陈澍, 邵莹莹, 付欣豪, 陈庆悟, 杜晓华, 谭成侠, 有机化学, 2022, 42, 3870.) doi: 10.6023/cjoc202205022
[16]	Cui, S. F.; Wang, Y.; Lv, J. S.; Damu, G. L. V.; Zhou, C. H. Sci. China Chem. 2012, 42, 1105 (in Chinese).
	( 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. pmid: 11893175
[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).
	( 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.) doi: 10.6023/cjoc201612052
[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).
	( 高文涛, 兰帅, 郑宏梅, 白仁青卓玛, 有机化学, 2015, 35, 144.) doi: 10.6023/cjoc201407014
[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).
	( 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.; Björkling, 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).
	( 吴功德, 王晓丽, Liming Zhang, 张方, 刘献锋, 刘从容, 有机化学, 2015, 35, 2537.) doi: 10.6023/cjoc201505046
[41]	Obijalska, E.; Błaszczyk, M.; Kowalski, M. K.; Mlostoń, G.; Heimgartner, H. J. Fluorine Chem. 2019, 220, 35. doi: 10.1016/j.jfluchem.2019.02.003
[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. doi: 10.1038/s41598-021-86424-7 pmid: 33846389
[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.; Ibáñez, I.; Murguía, M.; Fustero, S. J. Org. Chem. 2009, 74, 8988. doi: 10.1021/jo9016265 pmid: 19894729
[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. doi: 10.1016/j.ejmech.2014.04.042 pmid: 24835815

噻唑类化合物的合成研究进展