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. Although the parent thiazolidine is only of academic interest, some derivatives, i.e., the thiazolidines, are important, such as the antibiotic penicillin.

Thiazolidine

Names
Preferred IUPAC name 1,3-Thiazolidine[1]
Identifiers
CAS Number	504-78-9 Y
3D model (JSmol)	Interactive image
Beilstein Reference	102469
ChEBI	CHEBI:50120
ChEMBL	ChEMBL1916078
ChemSpider	10013 N
ECHA InfoCard	100.007.275
EC Number	208-002-5
Gmelin Reference	2171
PubChem CID	10444
UNII	I320806BKW Y
CompTox Dashboard (EPA)	DTXSID10198447
InChI InChI=1S/C3H7NS/c1-2-5-3-4-1/h4H,1-3H2 N Key: OGYGFUAIIOPWQD-UHFFFAOYSA-N N
SMILES C1CSCN1
Properties
Chemical formula	C3H7NS
Molar mass	89.16 g·mol−1
Density	1.131 g/cm3[2]
Boiling point	72 to 75 °C (162 to 167 °F; 345 to 348 K)[2] at 25 torr
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Preparation

Thiazolidine is prepared by the condensation of cysteamine and formaldehyde.^[3] Other thiazolidines may be synthesized by similar condensations. A notable derivative is 4-carboxythiazolidine (thioproline), derived from formaldehyde and cysteine. The 2-oxo-thiazolidine procysteine is produced from phosgenation of cysteine.

Derivatives

The penicillins are elaborate thiazolidine.

Useful thiazolidines include the drug pioglitazone, the antibiotic penicillin, and N-Methyl-2-thiazolidinethione, an accelerator for the vulcanization of chloroprene rubbers.^[4]

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.

Many thiazolidines are prepared from cysteine and related aminothiols.^[5] p-aminocinnamaldehyde is able to differentiate between cysteine and homocysteine. With cysteine, a buffered water solution of the aldehyde changes from yellow to colorless due to a secondary ring closing reaction of the imine. Homocysteine is unable to give ring closure and the color does not change.

See also

• Thiazole
• Thiazoline