噻唑类化合物的合成研究进展

doi:10.6023/cjoc202310007

摘要/Abstract

噻唑环是含氮、硫杂原子的五元芳杂环, 广泛存在于药物、天然产物和功能材料中, 目前已有很多关于合成噻唑化合物的研究报道. 本综述聚焦于介绍制备噻唑环的合成方法以及这些合成方法的底物适用范围, 希望能够帮助其他研究者高效地合成和应用噻唑化合物.

关键词: 噻唑, 五元杂芳烃, 合成方法, 应用

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

引用此文

张雅芳, 黄轩, 林琪, 钟海琼, 翁志强, 吴伟. 噻唑类化合物的合成研究进展[J]. 有机化学, 2024, 44(5): 1458-1479.

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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图/表 55

图式1. 2,4-二取代噻唑类化合物的高效合成方法

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

图式2. Hammer等合成噻唑化合物的策略

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

图式3. Togo等合成噻唑化合物的方法

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

图式4. β-环糊精催化合成噻唑和2-氨基噻唑

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

图式5. AMP催化合成噻唑化合物

Scheme 5. AMP-catalyzed synthesis of thiazoles

图式6. 超声促进合成噻唑的绿色方法

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

图式7. 研磨法合成2,4-二取代噻唑化合物

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

图式8. Pal等报道合成噻唑的方法

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

图式9. 李巍和Thota等合成噻唑化合物的方法

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

图式10. 1,3-二酮、(硫代)酰胺和NBS的一锅三组分反应

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

图式11. 董卫莉和Garcia等合成噻唑化合物的方法

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

图式12. 2-(烷基硫基)噻唑的合成方法

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

图式13. 炔烃与硫代酰胺的环化反应

Scheme 13. Cyclization reaction of alkynes with thioamides

图式14. BF3?OEt2促进CF3COCHN2和硫代甲酰胺或硫脲的环化反应

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

图式15. Fe3O4@维生素B1催化合成全取代噻唑衍生物

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

图式16. β-环糊精催化β-酮酸酯和硫(硒)脲合成噻(硒)唑

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

图式17. 黄原酸催化β-酮酸酯和硫(硒)脲合成噻(硒)唑

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

图式18. 微波辅助一锅法合成噻唑化合物

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

图式19. 可见光促进活性亚甲基酮和硫脲的环化反应

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

图式20. Yadav和Babu等合成2-氨基噻唑的方法

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

图式21. Na2CO3促进α-对甲苯磺酰氧基酮与硫脲衍生物合成2-氨基噻唑

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

图式22. α-溴代酮与硫脲的缩合反应

Scheme 22. Condensation reaction of α-bromoketone with thiourea

图式23. Rh2(OAc)4催化硫叶立德与硫脲的类卡宾插入/环化反应

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

图式24. I2/CuO催化一锅法串联环化反应

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

图式25. I2促进芳基甲基酮、DMSO和硫脲的串联反应

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

图式26. NaICl2催化合成2-氨基噻唑

Scheme 26. NaICl2-catalyzed synthesis of 2-aminothiazoles

图式27. 纳米壳聚糖催化酮和硫脲或硫脲衍生物的一锅反应

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

图式28. β-环糊精催化一锅法合成噻唑/硒唑化合物

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

图式29. 研磨法合成噻唑连接吡唑的化合物

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

图式30. Ablajan等合成噻唑环的方法

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

图式31. Kannan和Leite等报道的合成噻唑类化合物的方法

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

图式32. Fe3O4@SiO2@KIT-6催化合成噻唑衍生物

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

图式33. 哌嗪介导水杨醛、氨基脲和α-溴代酮的一锅法三组分反应

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

图式34. 无取代噻唑的合成

Scheme 34. Synthesis of non-substituted thiazole

图式35. KSCN/SiO2-RNH3OAc/Al2O3体系合成2-氨基噻唑化合物的方法

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

图式36. 串联反应合成噻唑衍生物的方法

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

图式37. 无金属合成2-氨基噻/硒唑化合物

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

图式38. 联烯基异硫氰酸酯的环化反应

Scheme 38. Cyclization reaction of allenyl isothiocyanate

图式39. 异硫氰酸酯与炔丙基胺的一锅法环化反应

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

图式40. TMG、炔酸酯和芳基异硫氰酸酯的三组分串联反应

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

图式41. 碱促进脒、异硫氰酸酯和α-溴代酯/酮的串联环化反应

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

图式42. Rangappa等合成4,5-二取代噻唑的系列研究工作

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

图式43. 端炔、磺酰叠氮和硫酯的串联反应

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

图式44. Sheldrake等报道合成5-芳基噻唑类化合物的方法

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

图式45. 5-(三氟甲基)-2-噻唑胺的合成

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

图式46. Sanz-Cervera等合成噻唑环的方法

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

图式47. Lawesson’s试剂介导烯酰胺的一步硫化-环化反应

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

图式48. 铁催化烯胺与单质硫的环化反应

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

图式49. 铜(II)催化胺、醛与硫元素的三组分反应

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

图式50. 酮、醛、铵盐和单质硫的四组分一锅法串联反应

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

图式51. 酰胺和单质硫高效合成4-羟基噻唑化合物的方法

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

图式52. 固相合成法制备2,4-二取代5-氨基甲酰噻唑衍生物

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

图式53. [3＋2]环加成反应合成2-三氟甲基噻唑化合物

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

图式54. 异噻唑与噻唑的光转化重置换过程

Scheme 54. Phototransposition process of isothiazole and thiazole

图1. 合成噻唑类化合物的总结和展望

Figure 1. Summary and prospect of synthesis of thiazoles

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