2-Aminothiazole

2-Aminothiazole is a heterocyclic amine featuring a thiazole core. It can also be considered a cyclic isothiourea. It possesses an odor similar to pyridine and is soluble in water, alcohols and diethyl ether. 2-Aminothiazole itself is mainly of academic interest, with few exceptions. It is a precursor to a sulfathiazole ("sulfa drugs"). 2-Aminothiazole can be used as a thyroid inhibitor in the treatment of hyperthyroidism.

2-Aminothiazole is prepared from paraldehyde, thiourea, and sulfuryl chloride.

2-Aminothiazoles

Like the parent, 2-aminothiazoles are often produced by the condensation of thiourea and an alpha-halo ketone.

In an adaptation of the Robinson-Gabriel synthesis, a 2-acylamino-ketone reacts with phosphorus pentasulfide.

Applications

Synthetic aminothiazoles - compounds containing the parent 2-aminothiazole as a subunit - are used in medicinal chemistry. Some examples are abafungin, acotiamide, amiphenazole, amthamine, avatrombopag, aztreonam, cefepime, cefixime, ceftizoxime, ceftiofur, ceftibuten, cefpirome, famotidine, meloxicam, and pramipexole.

References

1. 2-Aminooxazole
2. Cyanamide
3. Thiazole
4. Α-Halo ketone
5. C3H4N2S
6. Glossary of chemical formulae
7. Cefepime
8. Beta-ketoacyl-ACP synthase III
9. Cefdinir
10. 2-Imidazolidinethione
11. Cook–Heilbron thiazole synthesis
12. Discovery and development of cephalosporins
13. Chloroacetaldehyde
14. Ritanserin
15. Thiourea
16. Cefditoren
17. Bcr-Abl tyrosine-kinase inhibitor
18. Cdc25