Beyer method for quinolines

Doebner Reaction (Beyer Synthesis, Beyer Method for Quinolines)... 

Doebner-Miller reaction (Beyer method for quinolines). Synthesis of quinolines from primary aromatic amines and a,(3-unsaturated carbonyl compounds in acid catalysis. The carbonyl compounds may be prepared in situ from two molecules of aldehyde or an aldehyde and methyl ketone. The latter is known as the Beyer method. 

This reaction was initially reported by Doebner and von Miller in 1881 as a modification of the original Skraup Reaction, and it was subsequently modified by Beyer in 1886 It is an acidic condensation between primary aromatic amines (e.g., anilines) and Q ,j8-unsaturated carbonyl compounds (mostly o ,y3-unsaturated aldehydes) to give 2,3-disubstituted quinolines. Therefore, this reaction is generally known as the Doebner-Miller reaction, or Doebner-Miller synthesis." In addition, this reaction is also referred to as the Doebner-von Miller quinoline synthesis, Skraup-Doebner-von Miller reaction, Skraup-Doebner-von Miller quinoline synthesis, Doebner-Miller condensation, and Doebner-Miller Quinaldine Synthesis. For comparison, the modification from Beyer, known as the Beyer method for quinoline, is an acidic condensation between anilines and Q ,j8-unsaturated carbonyl compounds generated in situ from aldehyde or aldehyde and methyl ketone to afford 2,4-disubstituted quinolines." The optimal condition of this reaction is to heat the mixture of aniline/aldehyde (1 2) at 100°C for 6 h with hydrochloric acid and zinc chloride in addition, an oxidizing reagent is also needed in this reaction, such as nitrobenzene. However, it has been reported that A -alkylanilines are also formed in this reaction. The nature and... 

Beyer Method for Quinolines Biginelli Reaction Birch Reduction... 

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See also in sourсe #XX -- [ , ]

See also in sourсe #XX -- [ , ]

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