Thiazolines (or dihydrothiazoles) are a group of

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Iso ...

ic 5-membered

heterocyclic compound A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and ...

s containing both

sulfur Sulfur (or sulphur in British English) is a chemical element with the symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms form cyclic octatomic molecules with a chemical formula ...

and

nitrogen Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at se ...

in the ring. Although unsubstituted thiazolines are rarely encountered themselves, their

derivatives The derivative of a function is the rate of change of the function's output relative to its input value. Derivative may also refer to: In mathematics and economics * Brzozowski derivative in the theory of formal languages * Formal derivative, an ...

are more common and some are bioactive. For example, in a common

post-translational modification Post-translational modification (PTM) is the covalent and generally enzymatic modification of proteins following protein biosynthesis. This process occurs in the endoplasmic reticulum and the golgi apparatus. Proteins are synthesized by ribosome ...

, cysteine residues are converted into thiazolines. The name thiazoline originates from the

Hantzsch–Widman nomenclature In organic chemistry, Hantzsch–Widman nomenclature, also called the extended Hantzsch–Widman system (named for Arthur Rudolf Hantzsch and ), is a type of systematic chemical nomenclature used for naming heterocyclic parent hydrides having no ...

Isomers

2-Thiazoline, 3-Thiazoline und 4-Thiazoline

Three structural isomers of thiazoline exist depending on the position of the double bond. These forms do not readily interconvert and hence are not

tautomer Tautomers () are structural isomers (constitutional isomers) of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the relocation of a hydr ...

s. 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 di

alkylation Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting ...

thioamide A thioamide (rarely, thionamide, but also known as thiourylenes) is a functional group with the general structure R–CS–NR′R″, where R, R′, and R″ are organic groups. They are analogous to amides but they exhibit greater multiple bond ch ...

s by

Richard Willstatter Richard is a male given name. It originates, via Old French, from Old Frankish and is a compound of the words descending from Proto-Germanic ''*rīk-'' 'ruler, leader, king' and ''*hardu-'' 'strong, brave, hardy', and it therefore means 'stron ...

in 1909. 2-Thiazolines are commonly prepared from 2-aminoethanethiols (e.g. cysteamine). They may also be synthesized via the

Asinger reaction The Asinger-reaction (sometimes referred to as the Asinger-4 component reaction or A-4CR for short) is a multicomponent reaction for the synthesis of 3-thiazolines and other related heterocycles. It is named after Friedrich Asinger who first reporte ...

Applications

Many molecules contain thiazoline rings, one example being

Firefly luciferin Firefly luciferin (also known as beetle luciferin) is the luciferin, or light-emitting compound, used for the firefly (Lampyridae), railroad worm (Phengodidae), starworm (Rhagophthalmidae), and click-beetle (Pyrophorini) bioluminescent systems. I ...

, the light-emitting molecule in

fireflies The Lampyridae are a family of elateroid beetles with more than 2,000 described species, many of which are light-emitting. They are soft-bodied beetles commonly called fireflies, lightning bugs, or glowworms for their conspicuous production ...

. The amino acid

cysteine Cysteine (symbol Cys or C; ) is a semiessential proteinogenic amino acid with the formula . The thiol side chain in cysteine often participates in enzymatic reactions as a nucleophile. When present as a deprotonated catalytic residue, sometime ...

is produced industrially from substituted thiazole.

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 ...

is an intermediate in the industrial synthesis of L-

.{{Ullmann, author=Karlheinz Drauz, Ian Grayson, Axel Kleemann, Hans-Peter Krimmer, Wolfgang Leuchtenberger, Christoph Weckbecker, year=2006, doi=10.1002/14356007.a02_057.pub2

Isomers

Synthesis

Applications

See also

References