Thiazoline

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Thiazoline
2,3-Dihydrothiazole.svg
3-Thiazoline.svg
4,5-Dihydrothiazole.svg
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
3D model (JSmol)
ChemSpider
PubChem CID
Properties
C3H5NS
Molar mass 87.14 g·mol−1
AppearanceColorless liquids
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

Thiazolines (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]

Contents

The name thiazoline originates from the Hantzsch–Widman nomenclature.

Isomers

2-Thiazoline, 3-Thiazoline and 4-Thiazoline (from left to right) 2-Thiazoline, 3-Thiazoline und 4-Thiazoline.png
2-Thiazoline, 3-Thiazoline and 4-Thiazoline (from left to right)

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

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

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]

See also

Related Research Articles

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Organic chemistry Subdiscipline of chemistry

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Tropinone

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7
H
5
NS
. It is colorless, slightly viscous liquid. Although the parent compound, benzothiazole is not widely used, many of its derivatives are found in commercial products or in nature. Firefly luciferin can be considered a derivative of benzothiazole.

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Oxazoline

Oxazoline is a five-membered heterocyclic chemical compound containing one atom each of oxygen and nitrogen. It was likely first synthesized in 1884 but it was not until 5 years later that Siegmund Gabriel correctly assigned the structure. It was named in-line with the Hantzsch–Widman nomenclature and is part of a family of heterocyclic compounds, where it exists between oxazole and oxazolidine in terms of saturation.

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Thiopeptide

Thiopeptides are a class of peptide antibiotics produced by bacteria. They have antibiotic activity against Gram-positive bacteria, but little or no activity against Gram-negative bacteria. Many of the members of this class show activity against methicillin-resistant Staphylococcus aureus (MRSA) and are therefore subjects of research interest.

2-Aminothiazoline-4-carboxylic acid

2-Aminothiazoline-4-carboxylic acid (ACTA) is the organosulfur compound and a heterocycle with the formula HO2CCHCH2SCNH2N. This derivative of thiazoline is an intermediate in the industrial synthesis of L-cysteine, an amino acid. ACTA exists in equilibrium with its tautomer 2-iminothiazolidine-4-carboxylic acid.

References

  1. Walsh, Christopher T.; Nolan, Elizabeth M. (2008). "Morphing peptide backbones into heterocycles". Proceedings of the National Academy of Sciences USA. 105 (15): 5655–5656. doi:10.1073/pnas.0802300105. PMC   2311349 . PMID   18398003.
  2. Willstätter, Richard; Wirth, Theodor (1909). "Über Thioformamid". Chem. Ber. 42 (2): 1908–1922. doi:10.1002/cber.19090420267.
  3. 1 2 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.
  4. 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.CS1 maint: multiple names: authors list (link)