Asinger reaction
Chemical reaction
From Wikipedia, the free encyclopedia
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.[1] It is named after Friedrich Asinger who first reported it in 1956.[2]
| Asinger reaction | |
|---|---|
| Named after | Friedrich Asinger |
| Reaction type | Ring forming reaction |
| Identifiers | |
| RSC ontology ID | RXNO:0000688 |
Process
An α-halogenated carbonyl-component reacts with sodium hydrosulfide (NaSH) and forms a thiol in situ. The thiol reacts directly with another carbonyl component and ammonia to form a thiazoline. The reaction works also by using elemental sulphur, an α–substituted ketone, another carbonyl component and ammonia; in this case, a mixture of products is formed.
The formation of 3-thiazolines also occurs by using α-thioaldehyde or α-thioketone and ammonia.[3]
A simplified route of the Asinger-reaction was developed at Degussa. An α-halogenated carbonyl compound reacts with sodium hydrosulfide (NaSH) and forms a thiol in situ which reacts directly with aldehydes or ketones and ammonia to 3-thiazolines.[4] The chemical industry developed based on the Asinger-reaction multi stage processes for the production of pharmaceuticals like D-penicillamine[5] and the aminoacid DL-cysteine.[6]
