Thiazoline

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Thiazoline

From Wikipedia, the free encyclopedia

Thiazoline
Names



IUPAC names 2,3-Dihydrothiazole 2,5-Dihydrothiazole 4,5-Dihydrothiazole
Other names 2,3-Dihydro-1,3-thiazole or 4-thiazoline 2,5-Dihydro-1,3-thiazole or 3-thiazoline 4,5-Dihydro-1,3-thiazole or 2-thiazoline
Identifiers
CAS Number	(2,3): 504-79-0^Y (2,5): 24576-55-4^N (4,5): 504-79-0^N
3D model (JSmol)	(2,3): Interactive image (2,5): Interactive image (4,5): Interactive image
ChemSpider	(2,3): 133456 (2,5): 10541467 (4,5): 107368
PubChem CID	(2,3): 151424 (2,5): 15194654 (4,5): 120269
CompTox Dashboard (EPA)	(2,3): DTXSID70198448
InChI (2,3): InChI=1S/C3H5NS/c1-2-5-3-4-1/h1-2,4H,3H2 Key: OYJGEOAXBALSMM-UHFFFAOYSA-N (2,5): InChI=1S/C3H5NS/c1-2-5-3-4-1/h1H,2-3H2 Key: JLPUISACQXFVRC-UHFFFAOYSA-N (4,5): InChI=1S/C3H5NS/c1-2-5-3-4-1/h3H,1-2H2 Key: CBDKQYKMCICBOF-UHFFFAOYSA-N
SMILES (2,3): C1=CSCN1 (2,5): C1=NCSC1 (4,5): C1CSC=N1
Properties
Chemical formula	C₃H₅NS
Molar mass	87.14 g·mol⁻¹
Appearance	Colorless liquids
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

Thiazolines (/θaɪˈæzoʊliːnz/; or dihydrothiazoles) are a group of isomeric 5-membered heterocyclic compounds containing both sulfur and nitrogen in the ring. Although unsubstituted thiazolines are rarely encountered themselves, their derivatives are more common and some are bioactive. For example, in a common post-translational modification, cysteine residues are converted into thiazolines.^[1]

The name thiazoline originates from the Hantzsch–Widman nomenclature.

Isomers

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Three structural isomers of thiazoline exist depending on the position of the double bond. These forms do not readily interconvert and hence are not tautomers. Of these 2-thiazoline is the most common.

A fourth structure exists in which the N and S atoms are adjacent; this known as isothiazoline.

Synthesis

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Thiazolines were first prepared by dialkylation of thioamides by Richard Willstatter in 1909.^[2] 2-Thiazolines are commonly prepared from 2-aminoethanethiols (e.g. cysteamine).^[3] They may also be synthesized via the Asinger reaction.

Applications

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Many molecules contain thiazoline rings, one example being Firefly luciferin, the light-emitting molecule in fireflies. The amino acid cysteine is produced industrially from substituted thiazole.^[3] 2-Aminothiazoline-4-carboxylic acid is an intermediate in the industrial synthesis of L-cysteine.^[4]

References

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^ Walsh, Christopher T.; Nolan, Elizabeth M. (2008). "Morphing peptide backbones into heterocycles". Proceedings of the National Academy of Sciences USA. 105 (15): 5655–5656. Bibcode:2008PNAS..105.5655W. doi:10.1073/pnas.0802300105. PMC 2311349. PMID 18398003.
^ Willstätter, Richard; Wirth, Theodor (1909). "Über Thioformamid". Chem. Ber. 42 (2): 1908–1922. doi:10.1002/cber.19090420267.
^ ^a ^b Gaumont, Annie-Claude; Gulea, Mihaela; Levillain, Jocelyne (11 March 2009). "Overview of the Chemistry of 2-Thiazolines". Chemical Reviews. 109 (3): 1371–1401. doi:10.1021/cr800189z. PMID 19154153.
^ Karlheinz Drauz, Ian Grayson, Axel Kleemann, Hans-Peter Krimmer, Wolfgang Leuchtenberger, Christoph Weckbecker (2006). Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_057.pub2. ISBN 978-3527306732.{{cite encyclopedia}}: CS1 maint: multiple names: authors list (link)

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Category:

Thiazolines

Hidden categories:

Isomers

Synthesis

Applications

See also

References