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Definition: What is Fischer Indole Synthesis?
The Fischer indole synthesis is an organic reaction used to convert a phenylhydrazine and an aldehyde or ketone to an indole using an acid catalyst, like Brønsted or Lewis acids. An application of this reaction is the synthesis of antimigraine drugs belonging to the triptan class.
The history of this reaction goes back to 1883 when the reaction was first discovered by a German chemist Emil Fischer.
Examples of Fischer Indole Synthesis
The Fisher indole synthesis is used to synthesize 2-phenylindole and tetrahydrocarbazole.
Mechanism of Fischer Indole Synthesis
Phenylhydrazone is formed from a condensation reaction of phenylhydrazine and an aldehyde or ketone. The phenylhydrazone converts into an indole in the presence of an acid catalyst.
Question for Fischer indole synthesisTry yourself: What is the purpose of Fischer indole synthesis?View Solution
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FAQs on Fischer indole synthesis - Chemistry Optional Notes for UPSC
| 1. What is Fischer Indole Synthesis? |  |
Ans. Fischer Indole Synthesis is a chemical reaction used to synthesize indole compounds. It involves the cyclization of an aryl hydrazine and a carbonyl compound, typically an aldehyde or ketone, in the presence of an acid catalyst. The reaction proceeds through the formation of a reactive imine intermediate, which undergoes intramolecular cyclization to form the indole ring.
| 2. What are some examples of Fischer Indole Synthesis? | |
Ans. Some examples of Fischer Indole Synthesis include the synthesis of indole-3-carboxaldehyde from hydrazine hydrate and isatin, the synthesis of 2-phenylindole from acetophenone and phenylhydrazine, and the synthesis of 5-methylindole from 2-methylbenzaldehyde and methylhydrazine.
| 3. What is the mechanism of Fischer Indole Synthesis? | |
Ans. The mechanism of Fischer Indole Synthesis involves several steps. Firstly, the aryl hydrazine and carbonyl compound react to form an imine intermediate. This reaction is catalyzed by an acid, such as sulfuric acid. The imine then undergoes intramolecular cyclization, forming a five-membered imine intermediate. This intermediate tautomerizes to the final indole product through a series of proton transfers and rearrangements.
| 4. What are the key reagents and conditions required for Fischer Indole Synthesis? | |
Ans. The key reagents required for Fischer Indole Synthesis are an aryl hydrazine, a carbonyl compound (aldehyde or ketone), and an acid catalyst. Commonly used acid catalysts include sulfuric acid, hydrochloric acid, and phosphoric acid. The reaction is typically carried out at elevated temperatures, often under reflux conditions.
| 5. What are the applications of Fischer Indole Synthesis? | |
Ans. Fischer Indole Synthesis is widely used in organic synthesis to access various indole derivatives, which have diverse biological activities and pharmaceutical applications. Indole compounds are found in many natural products and can serve as building blocks for the synthesis of complex molecules. They are often utilized in medicinal chemistry for the development of drugs targeting a variety of diseases, including cancer, neurological disorders, and infectious diseases.
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