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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 ...
[7] [8] Hydrazone-based coupling methods are used in medical biotechnology to couple drugs to targeted antibodies (see ADC), e.g. antibodies against a certain type of cancer cell. The hydrazone-based bond is stable at neutral pH (in the blood), but is rapidly destroyed in the acidic environment of lysosomes of the cell.
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 .
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 ...
When exposed to an amine, reaction with acetaldehyde produces the enamine, which subsequently reacts with sodium nitroprusside to the imine. Finally, the iminium salt is hydrolysed to the bright blue [1] Simon-Awe complex. [3] [5]
Phenylacetaldehyde is an aldehyde that consists of acetaldehyde bearing a phenyl substituent; the parent member of the phenylacetaldehyde class of compounds. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an alpha-CH2-containing aldehyde and a member of ...
Acetaldehyde is a common electrophile in organic synthesis. [31] In addition reactions acetaldehyde is prochiral. It is used primarily as a source of the "CH 3 C + H(OH)" synthon in aldol reactions and related condensation reactions. [32] Grignard reagents and organolithium compounds react with MeCHO to give hydroxyethyl derivatives. [33]
[1] [2] The reaction has been variously termed a disulfiram-like reaction, alcohol intolerance, and acetaldehyde syndrome. [ 3 ] The prototypical drug of this group is disulfiram (brand name Antabuse), which acts as an acetaldehyde dehydrogenase inhibitor , preventing the metabolism of acetaldehyde into acetic acid , and is used in the ...