Thiazolidine

Thiazolidine is a heterocyclic organic compound with the formula (CH2)3(NH)S. It is a 5-membered saturated ring with a thioether group and an amine group in the 1 and 3 positions. It is a sulfur analog of oxazolidine. Thiazolidine is a colorless liquid.

Thiazolidine
Names
IUPAC name
Thiazolidine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.275
PubChem CID
UNII
CompTox Dashboard (EPA)
Properties
Chemical formula
 C3H7NS
Molar mass 89.16 g·mol−1
Density 1.131 g/cm3[1]
Boiling point 72 to 75 °C (162 to 167 °F; 345 to 348 K)[1] at 25 torr
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Derivatives, thiazolidines, are known. For example, the drug pioglitazone contains a thiazolidine ring. Another drug that contains a thiazolidine ring is the antibiotic penicillin.

Preparation

Thiazolidine is prepared as it was in its first reported synthesis, by the condensation of cysteamine and formaldehyde.[2] Other thiazolidines may be synthesized by similar condensations. A notable derivative is 4-carboxythiazolidine, derived from formaldehyde and cysteine.

Derivatives

N-Methyl-2-thiazolidinethione is an accelerator for the vulcanization of chloroprene rubbers.[3]

Thiazolidines functionalized with carbonyls at the 2 and 4 positions, the thiazolidinediones, are drugs used in the treatment of diabetes mellitus type 2. Rhodanine is a related bioactive species, featuring one carbonyl and one thiocarbonyl.

See also

References
  1. Thiazolindine
  2. Ratner, Sarah; Clarke, H. T. (1937). "Action of formaldehyde on cysteine". Journal of the American Chemical Society. 59: 200–6. doi:10.1021/ja01280a050.CS1 maint: uses authors parameter (link)
  3. Rüdiger Schubart (2000). "Dithiocarbamic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a09_001.
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