Thiazole

Thiazole, or 1,3-thiazole, is a clear to pale yellow flammable liquid with a carbons ^[1].

Thiazole is used for manufacturing biocides, fungicides, dyes.

Thiazoles and thiazolium salts

Thiazoles are a class of functional group. Thiazoles are aromatic.

The thiazole moiety is a crucial part of vitamin B1 (luciferin.

Thiazoles are structurally similar to transition metal carbene complexes.^{[citation needed]}

When the amino atom is cotton.

biomolecules; oxazoles are not.

Organic synthesis

Various laboratory methods exist for the organic synthesis of thiazoles.

• The Hantzsch thiazole synthesis (1889) is a reaction between phosphorus pentasulfide, and chloroacetone ^[3]. Another example ^[4] is given below:

• In an adaptation of the Robinson-Gabriel synthesis, a 2-acylamino-ketones reacts with phosphorus pentasulfide.
• In the Cook-Heilbron synthesis, an α-aminonitrile reacts with carbon disulfide.
• Certain thiazoles can be accessed though application of the Herz reaction.

Reactions

Thiazoles are characterized by larger pi-electron diamagnetic ring current.

The calculated pi-electron density marks C5 as the primary electrophilic site, and C2 as the nucleophilic site.

The reactivity of a thiazole can be summarized as follows:

• Deprotonation at C2: the negative charge on this position is stabilized as an Grignard reagents and organolithium compounds react at this site, replacing the proton

2-(trimethylsiliyl)thiazole ^[5] (with a ketenes

• Alkylation at nitrogen forms a thiazolium salt
• activating groups such as a methyl group in this bromination:

• chlorine with

• Organic oxidation at nitrogen gives the thiazole sulfoxide ^[6]:

• Thiazoles are hydrolysis with mercury chloride in water

• Thiazoles can react in electrocyclic ring openening and then to a 7-thia-2-azanorcaradiene in an 6-electron electrocyclic ring, closing before extruding the sulfur atom.

References

1. ^ The Chemistry of Heterocycles : Structure, Reactions, Syntheses, and Applications Theophil Eicher, Siegfried Hauptmann ISBN 3-527-30720-6
2. ^ A. J. Arduengo, J. R. Goerlich and W. J. Marshall (1997). "A Stable Thiazol-2-ylidene and Its Dimer". Liebigs Annalen 1997 (2): 365-374. doi:10.1002/jlac.199719970213.
3. ^ George Schwarz (1955). "2,4-Dimethylthiazole". Org. Synth.; Coll. Vol. 3: 332. 
4. ^ ^{a b} Mateo Alajarín, José Cabrera, Aurelia Pastor, Pilar Sánchez-Andrada, and Delia Bautista (2006). "On the [2+2] Cycloaddition of 2-Aminothiazoles and Dimethyl Acetylenedicarboxylate. Experimental and Computational Evidence of a Thermal Disrotatory Ring Opening of Fused Cyclobutenes". J. Org. Chem. 71 (14): 5328 - 5339. doi:10.1021/jo060664c.
5. ^ ^{a b} Alessandro Dondoni and Pedro Merino (1998). "Diastereoselective Homologation of D-(R)-Glyceraldehyde Acetonide using 2-(Trimethylsilyl)thiazole". Org. Synth.; Coll. Vol. 9: 952. 
6. ^ Elizabeta Amir and Shlomo Rozen (2006). "Easy access to the family of thiazole N-oxides using HOF·CH3CN". Chemical Communications 2006: 2262 - 2264. doi:10.1039/b602594c.