Thiazoline
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The name thiazoline originates from the Hantzsch–Widman nomenclature.
Isomers
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.
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Synthesis
Thiazolines were first prepared by dialkylation of thioamides by Richard Willstatter in 1909. 2-Thiazolines are commonly prepared from 2-aminoethanethiols (e.g. cysteamine). 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. 2-Aminothiazoline-4-carboxylic acid is an intermediate in the industrial synthesis of L-cysteine.