Review of the synthesis and biological activity of thiazoles

Figures & data

Figure 1. Resonating structures of thiazole.

Figure 2. Several bioactive thiazoles 1-4.

Scheme 1. Condensing α-chloroacetaldehyde 5 with thioformamide 6.

Scheme 2. Reaction of a thioamide 9 with α-halocarbonyl compounds 11.

Scheme 3. Synthesis of bisthiazole 13.

Scheme 4. Synthesis of Thiazolium salts 16.

Scheme 5. Synthesis of 2-aminothiazoles 18.

Scheme 6. Synthesis of 2-monosubstituted aminothiazoles 20.

Scheme 7. Synthesis of 2-disubstituted aminothiazoles 22 his method, initiated by Marchesini,^[23,81] in 1893 based on the reaction of an 1-chloropropan-2-one 14 with O-methyl carbamothioate 23 gave 2-hydroxythiazole derivatives 24.

Scheme 8. Synthesis of 2-hydroxythiazole derivatives 24.

Scheme 9. Cyclization of α-thiocyanatoketones 25.

Scheme 10. Synthesis of 2-mercapto-4-phenylthiazole 29.

Scheme 11. Synthesis of 2-mercapto-5-amino thiazoles 32.

Scheme 12. Synthesis of 5-aminothiazoles 35.

Scheme 13. Synthesis of thiazole derivatives based on diketone 38.

Scheme 14. Synthesis of 2,4,5-trisubstituted thiazoles 41.

Scheme 15. Synthesis of 2,4-diaminothiazole 44.

Scheme 16. Intramolecular cylization of N-(2-bromoprop-2-enyl)thioamides 45.

Scheme 17. Reaction of methyl benzoate derivatives 47 with phenylglycine 49.

Scheme 18. Synthesis of thiazoles 53, 57 and 58.

Scheme 19. Synthesis of thiazole derivatives 61.

Table 1. α-Halogenocarbonyls compounds.

Scheme 20. Synthesis of ethyl 5-isopropyl-2-methylthiazole-4-carboxylate 65.

Scheme 21. Synthesis of thiazoles 68.

Scheme 22. Synthesis of thiazoles 70.

Scheme 23. Synthesis of bis-thiazoles 77.

Scheme 24. Synthesis of bis-thiazolones 82–84.

Scheme 25. Synthesis of thiazole derivatives 88.

Scheme 26. Reaction of thioacetamide 89 with dimethyl acetylenedicarboxylate 92.

Scheme 27. Synthesis of thiazole derivatives 95.

Scheme 28. Synthesized bisthiazole derivatives 100.

Scheme 29. Synthesize of thiazole derivatives 103.

Scheme 30. Synthesize of tert-butyl 4-(4-(chloromethyl)thiazol-2-yl)piperidine-1-carboxylate 108.

Scheme 31. Synthesize of thiazoles 113.

Scheme 32. Synthesize of steroid thiazoles (116 and 118).

Scheme 33. Synthesize of bisthiazole 122 and 125.

Scheme 34. Synthesize of thiazole derivatives 128, 129 and 131.

Scheme 35. Synthesize of thiazole derivatives 136.

Scheme 36. Synthesis of bis-thiazoles 144–148.

Scheme 37. Synthesis of bis-thiazoles 156–162.

Scheme 38. Synthesis of pyrazolines 164 and thiazoles 167–169.

Scheme 39. Synthesis of thiazole derivatuves 172.

Scheme 40. Synthesis of thiazole derivatuves 177.

Scheme 41. Synthesis of thiazolone derivatuves 180.

Scheme 42. Reaction of compound 182 with hydrazonoyl halides 165 and 178.

Marchesini, G. Gazz. Chim. Ital. 1893, 23, 437.

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Marchesini, G. Gazz. Chim. Ital. 1894, 24, 65.

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