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Nenitzescu indole synthesis
The Nenitzescu indole synthesis is a chemical reaction that forms 5-hydroxyindole derivatives from benzoquinone and β-aminocrotonic esters.
This reaction was named for its discoverer, who first published it in 1929. It can be performed with a number of different combinations of R-groups, which include methyl, methoxy, ethyl, propyl, and H substituents. There is also a solid-state variation in which the reaction takes place on a highly cross-linked polymer scaffold. The synthesis is particularly interesting because indoles are the foundation for a number of biochemically important molecules, including neurotransmitters and a new class of antitumor compounds.
==Mechanism==
The mechanism of a Nenitzescu reaction consists of a Michael addition, followed by a nucleophilic attack by the enamine pi bond, and then an elimination.
The reaction was first published by Nenitzescu in 1929,〔 and has since been refined by Allen ''et al.''〔 In his 1966 publication, Allen and coworkers investigated the effects that different substituents on the benzoquinone starting material had on the arrangement of the final product. These steric effects also gave evidence that one of the two current proposed mechanisms was more likely than the other, which led to the publication of the mechanism shown above.
抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』
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