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Indole is an organic compound with the formula C 6 H 4 CCNH 3. Indole is classified as an aromatic heterocycle. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring. Indoles are derivatives of indole where one or more of the hydrogen atoms have been replaced by substituent groups.
The first indole alkaloid, strychnine, was isolated by Pierre Joseph Pelletier and Joseph Bienaimé Caventou in 1818 from the plants of the genus Strychnos. The correct structural formula of strychnine was determined only in 1947, although the presence of the indole nucleus in the structure of strychnine was established somewhat earlier.
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Despite its long history, this classical reaction had received relatively little attention in comparison with other methods for indole synthesis, owing to the reactions harsh conditions, poor yields and unpredictable regioselectivity. Recently, milder methods have been developed, including the use of lithium bromide as a catalyst and an ...
Indole-3-acetic acid (IAA, 3-IAA) is the most common naturally occurring plant hormone of the auxin class. It is the best known of the auxins, and has been the subject of extensive studies by plant physiologists. [1] IAA is a derivative of indole, containing a carboxymethyl substituent. It is a colorless solid that is soluble in polar organic ...
Baeyer–Emmerling indole synthesis is a method for synthesizing indole from a (substituted) ortho-nitrocinnamic acid and iron powder in strongly basic solution. [ 1 ] [ 2 ] This reaction was discovered by Adolf von Baeyer and Adolph Emmerling in 1869.
For example, a phenylhydrazone product can be heated in the presence of strong acid to produce an indole via the Fischer indole synthesis. [7] [8] If there is a leaving group elsewhere in the Japp–Klingemann product, the hydrazone instead can cyclize at that site via a substitution reaction to give a pyrazole.
3,3′-Diindolylmethane (DIM) is a compound derived from the digestion of indole-3-carbinol, found in cruciferous vegetables, such as broccoli, Brussels sprouts, cabbage and kale. [1] It and its parent compound – indole-3-carbinol – are under laboratory research to determine their possible biological properties, particularly in anti-cancer ...