3-Dimethylaminoacrolein

[3] It is a stable chemical, unlike the parent compound 3-aminoacrolein [ru],[6] and can be used as a comparably nontoxic precursor for the genotoxic, mutagenic, and potentially carcinogenic malondialdehyde.

Therefore, 3-dimethylaminoacrolein and vinamidines derived there from (composed of vinylogous amidines) or vinamidinium salts (substituted 1,5-diazapentadienes)[8] can be used as reactive molecular building blocks for the formation of nitrogen-containing heterocycles, such as pyridines, pyrimidines, pyrroles or pyrazoles.

[11] They react with phosgene and dimethylformamide (which forms in-situ the Vilsmeier reagent) in 68% yield to 3-ethoxypropenylidene dimethylammonium chloride, an enol ether iminium salt.

[4] The amidine formed with 2-naphthylamine and the dimethyl sulfate adduct can be cyclized with sodium methoxide to give benzo[f]quinoline (1-azaphenanthrene).

[17][18] Occasionally, the iminium salt from the reaction of the Vilsmeier reagent and the vinyl ether (a precursor of 3-dimethylaminopropenal) is directly used for synthesis, e. g. for pyrazoles.

The salt reacts also with cyclopentadiene in the presence of sodium amide in liquid ammonia to give the aminofulvene derivative.

[22] Lactones (e.g. γ-butyrolactone) or cyclic ketones (such as cyclopentanone) form with the vinylamidinium salt of 3-dimethylaminoacrolein and dimethylamine hydrochloride the corresponding dienaminones in 91% and 88% yield.

Synthese of Dimethylaminoacrolein from propynal.
Synthese of Dimethylaminoacrolein from propynal .
Synthesis of dimethylaminoacrolein as described by Arnold.
Synthesis of dimethylaminoacrolein as described by Arnold.
Synthesis of 3-dimethylaminoacrolein via isobutylvinylether.
Synthesis of 3-dimethylaminoacrolein via isobutylvinylether.
Reaktionen vinyloger Amidine nach Bredereck
Reaktionen vinyloger Amidine nach Bredereck
Synthese von 2-Aminopyrimidin aus 3-Dimethylaminoacrolein
Synthese von 2-Aminopyrimidin aus 3-Dimethylaminoacrolein
Synthese von Benzo[f]chinolin mit 3-Dimethylaminoacrolein
Synthese von Benzo[f]chinolin mit 3-Dimethylaminoacrolein
Synthese von substituiertem Pyrrol
Synthese von substituiertem Pyrrol
Synthese einer Fluvastatin-Zwischenstufe mit 3-Dimethylaminoacrolein
Synthese einer Fluvastatin-Zwischenstufe mit 3-Dimethylaminoacrolein
Pyrazolsynthese mit 3-Dimethylaminoacrolein
Pyrazolsynthese mit 3-Dimethylaminoacrolein
Synthese des 1,3-Bis(dimethylamino)trimethinium perchlorats
Synthese des 1,3-Bis(dimethylamino)trimethinium perchlorats
Reaktion von 3-Dimethylaminoacrolein mit gamma-Butyrolacton
Reaktion von 3-Dimethylaminoacrolein mit gamma-Butyrolacton
Synthese von Carbazolen und Benzothiophenen
Synthese von Carbazolen und Benzothiophenen
Synthese von Thiophenen und Pyrrolen
Synthese von Thiophenen und Pyrrolen
Synthese von 2-Chlornicotinsäure mit 3-Dimethylaminoacrolein
Synthese von 2-Chlornicotinsäure mit 3-Dimethylaminoacrolein