What is indole formation?
What is indole formation?
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. The reaction was discovered in 1883 by Emil Fischer.
How is indole synthesized?
Indole can still be synthesized, however, using the Fischer indole synthesis by reacting phenylhydrazine with pyruvic acid followed by decarboxylation of the formed indole-2-carboxylic acid. This has also been accomplished in a one-pot synthesis using microwave irradiation.
How many method are there for synthesis of indole system?
In Type 7, the benzene ring has been derived from an existing cyclohexane, and in Type 8, the benzene ring has been built onto an existing pyrrole. Finally, in Type 9, both rings have been constructed. The nine types of indole synthesis. There are several name reactions associated with indole synthesis.
What is a indole in chemistry?
indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter.
How is indole prepared by Fischer indole synthesis?
The synthesis of Fischer indole is an organic reaction used by an acid catalyst to convert phenyl hydrazine and an aldehyde or ketone to an indole. By the acid catalysed reaction of the hydrazine with the carbonyl, the cycle starts with the formation of a phenylhydrazone.
Where are indoles found?
Overview. Indole-3-carbinol is a substance found in vegetables such as broccoli, Brussels sprouts, cabbage, collards, cauliflower, kale, mustard greens, turnips, and rutabagas. It can also be produced in the laboratory.
How do you make phenylhydrazine?
Phenylhydrazine is prepared by oxidizing aniline with sodium nitrite in the presence of hydrogen chloride to form the diazonium salt, which is subsequently reduced using sodium sulfite in the presence of sodium hydroxide to form the final product.
What are the properties and occurrence of indole?
General properties and occurrence. Indole is a solid at room temperature. It occurs naturally in human feces and has an intense fecal odor. At very low concentrations, however, it has a flowery smell, and is a constituent of many flower scents (such as orange blossoms) and perfumes. It also occurs in coal tar.
What are some examples of indolic compounds?
Other indolic compounds include the plant hormone auxin (indolyl-3-acetic acid, IAA), tryptophol, the anti-inflammatory drug indomethacin, and the betablocker pindolol. The name indole is a portmanteau of the words ind igo and ole um, since indole was first isolated by treatment of the indigo dye with oleum.
What is the Vilsmeier Haack formylation of indole?
Vilsmeier–Haack formylation of indole will take place at room temperature exclusively at C3. Since the pyrrollic ring is the most reactive portion of indole, electrophilic substitution of the carbocyclic (benzene) ring generally takes place only after N1, C2, and C3 are substituted.
Where does indindole undergo electrophilic substitution?
Indole undergoes electrophilic substitution, mainly at position 3 (see diagram in right margin).
