Über die Darstellung und die Reaktionsfähigkeit des β‐Methylchinolins

Wislicenus, Wilhelm; Elvert, Heinrich

doi:10.1002/cber.190904201183

Cited by 9 publications

(1 citation statement)

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“…The earliest example of this type of condensation is the synthesis of flavaniline by heating acetanilide with zinc chloride. The constitution of this substance and the mechanism of its synthesis were, however, elucidated by Besthorn and Fischer (13) only after Friedlaender (84) loses water and forms 3-methylquinoline (228). When acetanilide is heated with zinc chloride, the acetyl group migrates to the ortho and para positions and the aminoacetophenone thus formed yields flavaniline (IV) (13).…”

mentioning

confidence: 99%

The Chemistry of Quinolines.

Manske¹

1942

Chem. Rev.

182

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mentioning

confidence: 99%

The Chemistry of Quinolines.

Manske¹

1942

Chem. Rev.

182

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TheFriedländer Synthesis of Quinolines

1982

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Friedländer prepared quinoline in 1882 by the condensation of o ‐aminobenzaldehyde with acetaldehyde in the presence of sodium hydroxide. This type of reaction has since been extensively explored and, in its most general form, can be defined as an acid‐ or base‐catalyzed condensation followed by a cyclodehydration between an o ‐amino‐substituted aromatic aldehyde, ketone, or derivative thereof with an appropriately substituted aldehyde, ketone, or other carbonyl compound containing a reactive α‐methylene group. Some quinolines can also be prepared simply by heating a mixture of the reactants with or without a solvent. Because both reactants contain a carbonyl group, certain quinolines can be prepared from a single starting compound. Of historic interest is the formation of the dye flavaniline from acetanilide. When acetanilide is heated with zinc chloride, the acetyl group of some molecules migrates to the ortho position, and that of others migrates to the para position. The resulting mixture of o ‐acetylaniline and p ‐acetylaniline then undergoes Friedländer condensation to form flavaniline. Two related quinoline syntheses, the Pfitzinger reaction and the Niementowski reaction, can be considered as extensions of the Friedländer synthesis. The Pfitzinger reaction uses an isatic acid or isatin and the Niementowski reaction uses an anthranilic acid for condensation to form a 4‐quinolinecarboxylic acid and a 4‐hydroxyquinoline, respectively. Several other related reactions, such as the Combes quinoline synthesis, the Doebner–Miller quinoline synthesis, and the Skraup quinoline synthesis, use different types of starting compounds. It is of interest that all of the six aforementioned syntheses of quinolines were discovered within a period of 14 years in the latter part of the nineteenth century, undoubtedly reflecting many scientific interests and commercial activities at that time, including the isolation of quinolines from coal tar, the manufacture of dyes, and studies of natural products such as alkaloids.

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Alkylquinolines and Arylquinolines

Claret

Osborne

1982

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Über die Darstellung und die Reaktionsfähigkeit des β‐Methylchinolins

Cited by 9 publications

References 1 publication

The Chemistry of Quinolines.

The Chemistry of Quinolines.

TheFriedländer Synthesis of Quinolines

Alkylquinolines and Arylquinolines

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