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Isoquinoline and quinoline are benzopyridines, which are composed of a benzene ring fused to a pyridine ring. In a broader sense, the term isoquinoline is used to make reference to isoquinoline derivatives. 1-Benzylisoquinoline is the structural backbone in many naturally occurring alkaloids such as papaverine.
The reaction below shows the acid-promoted synthesis of isoquinoline from benzaldehyde and a 2,2-dialkoxyethylamine. [5]Pomeranz-Fritsch-Reaktion-Übersichtsreaktion. Various alkyl groups, e.g. methyl and ethyl groups, can be used as substituent R.
The reaction is most notably used in the synthesis of dihydroisoquinolines, which can be subsequently oxidized to isoquinolines. A general scheme of the Bischler-Napieralski reaction. Mechanisms
Therefore, studies in which either the product or an intermediate is an isoquinoline, the Gabriel–Colman rearrangement can be utilized. This reaction has been utilized in the production of intermediates for the synthesis of potential anti-inflammatory agents. [7]
The reaction mechanism occurs by initial formation of an iminium ion (2) followed by electrophilic addition at the 3-position, in accordance with the expected nucleophilicity of indoles, to give the spirocycle 3. After migration of the best migrating group, deprotonation gives the product (5). The mechanism of the Pictet–Spengler reaction
The Combes quinoline synthesis is a chemical reaction, which was first reported by Combes in 1888. Further studies and reviews of the Combes quinoline synthesis and its variations have been published by Alyamkina et al ., [ 1 ] Bergstrom and Franklin, [ 2 ] Born, [ 3 ] and Johnson and Mathews.
This reaction is also known as the Skraup-Doebner-Von Miller quinoline synthesis, and is named after the Czech chemist Zdenko Hans Skraup (1850–1910), and the Germans Oscar Döbner (Doebner) (1850–1907) and Wilhelm von Miller (1848–1899).
The mechanism of the Pfitzinger reaction. The reaction of isatin with a base such as potassium hydroxide hydrolyses the amide bond to give the keto-acid 2. This intermediate can be isolated, but is typically not. A ketone (or aldehyde) will react with the aniline to give the imine (3) and the enamine (4).