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The Asinger-reaction was invented in 1956 by Friedrich Asinger 1. The Asinger-reaction is a multicomponent reaction and is classified as A-4CR (short for Asinger-4 component reaction):
An α-halogenated carbonyl-component reacts with sodium-hydrogensulfide NaSH and forms in situ a Thiole. The thiole reacts directly with another carbonyl-component and ammonia to form Thiazolines. The reaction works also by using sulphur, an in α–position substitutable ketone, a further carbonyl-component and ammonia under formation of mixtures1.
The formation of 3-Thiazolines also occurs by using α-thioaldehyde or α-thioketone and ammonia2.
A simplyfied route of the Asinger-reaction was developed by Degussa. An α-halogenated carbonyl-compound reacts with sodium hydrogensulfide NaSH and creates in situ Thioles, which reacts directly with aldehydes or ketones and ammonia to 3-thiazolines.3. The chemical industry developed based on the Asinger-reaction multi stage processes for the production of pharmaceuticals like D-Penicillamine4 and the aminoacid DL-cysteine5.
References
- ^ a b Friedrich Asinger: Über die gemeinsame Einwirkung von Schwefel und Ammoniak auf Ketone Angewandte Chemie 68 (1956) 413.
- ^ Friedrich Asinger und Manfred Thiel: Einfache Synthesen und chemisches Verhalten neuer heterocyclischer Ringsysteme, Angewandte Chemie 70 (1958) 667–683.
- ^ Karlheinz Drauz, Hans Günter Koban, Jürgen Martens und Werner Schwarze: Phosphonic and Phosphinic Acid Analogs of Penicillamine, Liebigs Annalen der Chemie 1985, 448-452.
- ^ Wolfgang Weigert, Heribert Offermanns und Paul Scherberich : D-Penicillamin - Herstellung und Eigenschaften, Angewandte Chemie 87 (1975) 372-378 ; Angewandte Chemie-International Edition 14 (1975) 330-336.
- ^ Jürgen Martens, Heribert Offermanns und Paul Scherberich : Eine einfache Synthese von racemischem Cystein, Angewandte Chemie 93 (1981) 680; Angewandte Chemie-International Edition 20 668 (1981).
Literature
- Friedrich Asinger (1956). "Chemiker-Treffen Salzburg: Über die einfache und ergiebige Synthese von Thiazolonen". Angewandte Chemie 68 (11): 377. doi:.
- Friedrich Asinger (1956). "Über die gemeinsame Einwirkung von Schwefel und Ammoniak auf Ketone". Angewandte Chemie 68 (12): 413. doi:.
- Imre Schlemminger, Hans-Hermann Janknecht, Wolfgang Maison, Wolfgang Saak and Jürgen Martens (2000). "Synthesis of the first enantiomerically pure 3-thiazolines via Asinger reaction". Tetrahedron Letters 41 (38): 7289–7292. doi:.
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- This page was last modified on 9 July 2008, at 20:17.
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