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.
This reaction can be catalyzed by Brønsted acids such as HCl, H2SO4, polyphosphoric acid and p-toluenesulfonic acid or Lewis acids such as boron trifluoride, zinc chloride, and aluminium chloride.
Several reviews have been published.[3][4][5]
^Fischer, E.; Jourdan, F. (1883). "Ueber die Hydrazine der Brenztraubensäure". Berichte der Deutschen Chemischen Gesellschaft. 16 (2): 2241–2245. doi:10.1002/cber.188301602141.
^Fischer, E.; Hess, O. (1884). "Synthese von Indolderivaten". Berichte der Deutschen Chemischen Gesellschaft. 17 (1): 559–568. doi:10.1002/cber.188401701155.
^van Order, R. B.; Lindwall, H. G. (1942). "Indole". Chemical Reviews. 30 (1): 69–96. doi:10.1021/cr60095a004.
^Robinson, B. (1963). "The Fischer Indole Synthesis". Chemical Reviews. 63 (4): 373–401. doi:10.1021/cr60224a003.
^Robinson, B. (1969). "Studies on the Fischer indole synthesis". Chemical Reviews. 69 (2): 227–250. doi:10.1021/cr60258a004.
and 24 Related for: Fischer indole synthesis information
The Fischerindolesynthesis is a chemical reaction that produces the aromatic heterocycle indole from a (substituted) phenylhydrazine and an aldehyde...
by Emil Fischer. Although the synthesis of indole itself is problematic using the Fischerindolesynthesis, it is often used to generate indoles substituted...
The Bartoli indolesynthesis (also called the Bartoli reaction) is the chemical reaction of ortho-substituted nitroarenes and nitrosoarenes with vinyl...
rearrangement, Claisen rearrangement, Carroll rearrangement, and the Fischerindolesynthesis. Sigmatropic rearrangements are concisely described by an order...
Emil Fischer (1886) "Indole aus Phenylhydrazin" (Indole from phenylhydrazine), Annalen der Chemie, vol. 236, pages 126-151; for Fischer'ssynthesis of skatole...
The Nenitzescu indolesynthesis is a chemical reaction that forms 5-hydroxyindole derivatives from benzoquinone and β-aminocrotonic esters. This reaction...
atoms including one quaternary one. The synthesis of ring II was accomplished with a Fischerindolesynthesis using phenylhydrazine 1 and acetophenone...
[(CH3)2N]2CH2 + H2O Aminals are encountered in, for instance, the Fischerindolesynthesis. Several examples exist in nature. Naturally occurring aminals...
hydralazine. In the course of his classic investigation on the Fischerindolesynthesis, Emil Fischer prepared the first pyridazine via the condensation of phenylhydrazine...
structurally and pharmacologically related to metralindole. The Fischerindolesynthesis between p-Tolylhydrazine Hydrochloride [637-60-5] (1) and 1,2-Cyclohexanedione...
C6(CH3)6 + 3 CH4 + 15 H2O Other examples include catalyzing (A) the Fischerindolesynthesis, and also (B) Friedel-Crafts acylation reactions involving activated...
Phenylhydrazine is used to prepare indoles by the Fischerindolesynthesis, which are intermediates in the synthesis of various dyes and pharmaceuticals...
hydrazine derivatives. This reaction is particularly useful in the Fischerindolesynthesis of triptan compounds and indometacin. The use of sodium dithionite...
azoxy-compounds and, with her husband, postulated a mechanism for the FischerIndoleSynthesis. Based on this mechanism and working off the pyrrole syntheses...
PMC 3151320. PMID 21661087. Jewett, John C.; Bertozzi, Carolyn R. (2011). "Synthesis of a fluorogenic cyclooctyne activated by Cu-free click chemistry". Organic...
Pyrrolidine, the saturated hydrogenated analog Derivatives of pyrrole include indole, a derivative with a fused benzene ring. Wikimedia Commons has media related...
was the first to propose the correct formula for indole in 1869, after publishing the first synthesis three years earlier. His contributions to theoretical...
hypocotyl fragments. Wine chemistry Indole-3-carbinol Indole-3-butyric acid Tryptophol has known uses in the synthesis of Prodolic acid & Methindizate. Cornford...
reaction, as well as in the synthesis of indoles, for example: Baeyer–Emmerling indolesynthesis, Bartoli indolesynthesis. In the Saville reaction, mercury...
its use in the synthesis of banana oil, isoamyl alcohol is also an ingredient of Kovac's reagent, used for the bacterial diagnostic indole test. It is also...