This slides discusses about the heterocyclic compound thiazole. i.e.Five membered ring with two hetero atom such as sulphur and nitrogen.

1. Heterocyclic compound- Thiazole
Lecture by
S.Mathivanan.,M.Pharm
Asst Professor
Pharmacy

2. Thiazole nucleus is a heterocyclic organic
compound bearing both sulfur and nitrogen
atom at 1,3 position with five-member
heterocyclic ring

3. • Thiazole molecules used as an intermediate,
chemical in synthetic drugs, fungicides and
dyes in industries.
• A thiazole ring present naturally in the
essential vitamin B1 thaimin.

4. • Various derivatives of thiazole nucleus is the aim of
research due to their importance in various applications.
• Derivatives of thiazole heteroatom used as reactants,
intermediaries in the various industries like
agrochemical, pharmaceutical and the pesticides
industry.
• Most of the derivatives of thiazole were synthesized to
achieve the industrial, biological, and medicinal target by
numerous research scholar and scientist in R&D
laboratories.

5. Molecular and electronic structure
• Thiazole rings are planar and aromatic. Thiazoles are characterized by
larger pi electron delocalization than the corresponding oxazoles and
have therefore greater aromaticity.
• This aromaticity is evidenced by the chemical shift of the ring protons
in proton NMR spectroscopy (between 7.27 and 8.77 ppm), clearly
indicating a strong diamagnetic ring current.
• The calculated pi-electron density marks C5 as the primary site for
electrophilic substitution, and C2 as the site for nucleophilic
substitution.

6. Physical properties
• Thiazole compound have a clear to pale yellow
liquid.
• Odor similar to pyridine and its
• Boiling point is 116- 118oC.
• The specific gravity of thiazole is 1.2
• Sparingly soluble in water.
• Soluble in alcohol and ether.

7. Properties
1. Aromaticity

8. Properties
1. Aromaticity

9. Synthesis
1. Gabriel synthesis

10. Synthesis
1. Gabriel synthesis
Mechanism

11. Synthesis
2. From an α- Hydroxy - Carbonyl Component
( Hantzsch Thiazole Synthesis)

12. Synthesis
2. From an α- Hydroxy - Carbonyl Component
( Hantzsch Thiazole Synthesis)
Mechanism

13. Synthesis
3. From an thiocyanate salts

15. Reactions
1. Electrophilic addition to N
a. Protonation (basic property)

16. Reactions
2. Electrophilic substitution to C

17. Reactions
2. Electrophilic substitution to C

18. Reactions

19. Diels alder reaction

20. Medicinal uses

21. Medicinal uses