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The Fischer indole synthesis is a chemical reaction that produces the aromatic heterocycle indole from a (substituted) phenylhydrazine and an aldehyde or ketone under acidic conditions. [1] [2] The reaction was discovered in 1883 by Emil Fischer. Today antimigraine drugs of the triptan class are often synthesized by this method. The Fischer ...
Phenylhydrazine was the first hydrazine derivative characterized, reported by Hermann Emil Fischer in 1875. [7] [8] He prepared it by reduction of a phenyl diazonium salt using sulfite salts. Fischer used phenylhydrazine to characterize sugars via formation of hydrazones known as osazones with the sugar aldehyde. He also demonstrated in this ...
Hydrazine, organohydrazines, and 1,1-diorganohydrazines react with aldehydes and ketones to give hydrazones. Phenylhydrazine reacts with reducing sugars to form hydrazones known as osazones, which was developed by German chemist Emil Fischer as a test to differentiate monosaccharides. [4] [5]
Phenylhydrazine and 2,4-dinitrophenylhydrazine had been used historically in analytical chemistry to detect and identify compounds with carbonyl groups. Phenylhydrazine was used to study the structure of carbohydrates, because the reaction of the sugar's aldehyde groups lead to well crystallizing phenylhydrazones or osazones.
The Fischer indole synthesis is a chemical reaction that produces the aromatic heterocycle indole from a (substituted) phenylhydrazine and an aldehyde or ketone under acidic conditions. [19] [20] The reaction was discovered in 1883 by Hermann Emil Fischer. The Fischer indole synthesis. The choice of acid catalyst is very important.
Borsche–Drechsel cyclization is the central step in Borsche–Drechsel carbazole synthesis, where in the first step phenylhydrazine is condensed with cyclohexanone to form the cyclohexanone phenylhydrazone, and in the final step the resulting tetrahydrocarbazole is oxidized to carbazole itself.
The Wolff–Kishner reduction is a reaction used in organic chemistry to convert carbonyl functionalities into methylene groups. [1] [2] In the context of complex molecule synthesis, it is most frequently employed to remove a carbonyl group after it has served its synthetic purpose of activating an intermediate in a preceding step.
There in 1875, he discovered and named hydrazines, including unsymmetrical dimethylhydrazine, which became important much later during the Space Race, and phenylhydrazine. [2] The latter compound reacts with carboxylic compounds (aldehydes and ketones) producing crystalline solids. The phenylhydrazones of sugars allowed him to develop his work ...