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2-Aminothiazole

| NFPA-H = 2 | NFPA-F = 0 | NFPA-R = 0 | NFPA-S =

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.

:[[Image:HantzschThiazole-Synthesis.png|left|500px|Hantsch Thiazole Synthesis]]

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.

See a related compound called 2-Amino-2-thiazoline [1779-81-3].

References

References

  1. "2-Aminothiazole".
  2. (2000). "Ullmann's Encyclopedia of Industrial Chemistry".
  3. (1955). "Zur Synthese von 2-Amino-thiazolderivaten". Helvetica Chimica Acta.
  4. (1939). "2-Amino-4-methylthiazole".
  5. (2014). "Synthesis of 4,5-Disubstituted 2-Aminothiazoles from α,β-Unsaturated Ketones: Preparation of 5-Benzyl-4-methyl-2-aminothiazolium Hydrochloride Salt". Organic Syntheses.
  6. (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.]].
  7. (2016). "Recent Developments of 2-Aminothiazoles in Medicinal Chemistry". European Journal of Medicinal Chemistry.
  8. (2021). "2-Aminothiazole: A privileged scaffold for the discovery of anti-cancer agents". European Journal of Medicinal Chemistry.
  9. (1983). "2-Amino-2-thiazoline hydrochloride". Drugs of the Future.
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