Thiazoline
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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 | |
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| Properties | |
Chemical formula |
C3H5NS |
Molar mass |
7001871400000000000♠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). | |
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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]
The name thiazoline originates from the Hantzsch–Widman nomenclature.
Contents
1 Isomers
2 Synthesis
3 Applications
4 See also
5 References
Isomers
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]
See also
Thiazole - an analogue with 2 double bonds
Thiazolidine - an analogue with no double bonds
Oxazoline - an analogue with O in place of S
References
^ Walsh, Christopher T.; Nolan, Elizabeth M. (2008). "Morphing peptide backbones into heterocycles". Proceedings of the National Academy of Sciences USA. 105: 5655–5656. doi:10.1073/pnas.0802300105. PMC 2311349..mw-parser-output cite.citation{font-style:inherit}.mw-parser-output .citation q{quotes:"""""""'""'"}.mw-parser-output .citation .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .citation .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/12px-Wikisource-logo.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-maint{display:none;color:#33aa33;margin-left:0.3em}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}
^ Willstätter, Richard; Wirth, Theodor (1909). "Über Thioformamid". Chem. Ber. 42: 1908–1922. doi:10.1002/cber.19090420267.
^ ab 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.
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