Top Qs
Timeline
Chat
Perspective

Gewald reaction

Organic reaction From Wikipedia, the free encyclopedia

Remove ads

The Gewald reaction (or the Gewald aminothiophene synthesis) is an organic reaction involving the condensation of a ketone (or aldehyde when R2 = H) with a α-cyanoester in the presence of elemental sulfur and base to give a poly-substituted 2-amino-thiophene.[1][2]

Thumb
The Gewald reaction
Quick Facts Identifiers ...

The reaction is named after the German chemist Karl Gewald [de].[3][4][5]

Remove ads

Reaction mechanism

The reaction mechanism of the Gewald reaction was elucidated 30 years after the reaction was discovered.[6] The first step is a Knoevenagel condensation between the ketone (1) and the α-cyanoester (2) to produce the stable intermediate 3. The mechanism of the addition of the elemental sulfur is unknown. It is postulated to proceed through intermediate 4. Cyclization and tautomerization will produce the desired product (6).

Thumb
The mechanism of the Gewald reaction

Microwave irradiation has been shown beneficial to reaction yields and times.[7]

Remove ads

Variations

In one variation of the Gewald reaction a 3-acetyl-2-aminothiophene is synthesized starting from a dithiane (an adduct of sulfur and acetone if R = CH3 or acetaldehyde if R = H) and the sodium salt of cyanoacetone which in itself is very unstable:[8]

Thumb
1-(2-Amino-4-methyl-3-thienyl)ethanone synthesis

References

Loading related searches...

Wikiwand - on

Seamless Wikipedia browsing. On steroids.

Remove ads