Chemistry:Stollé synthesis
From HandWiki
The Stollé synthesis is a series of chemical reactions that produce oxindoles from anilines and α-haloacid chlorides (or oxalyl chloride).[1][2][3][4]
The first step is an amide coupling, while the second step is a Friedel–Crafts reaction.[5][6] An improved procedure has been developed.[7][8]
See also
References
- ↑ Stollé, R. (1913). "Über eine neue Methode zur Darstellung N-substituierter Isatine. (Vorläufige Mitteilung)" (in German). Ber. 46 (3): 3915–3916. doi:10.1002/cber.191304603186. https://zenodo.org/record/1426535.
- ↑ Stollé, R. (1914). "Über Phenyl-oxindol" (in German). Ber. 47 (2): 2120–2122. doi:10.1002/cber.191404702112. https://zenodo.org/record/1426551.
- ↑ Stollé, R.; Bergdoll, R.; Luther, M.; Auerhahn, A.; Wacker, W. (1922). "Über N-substituierte Oxindole und Isatine" (in German). J. Prakt. Chem. 105 (1): 137–148. doi:10.1002/prac.19221050111. https://zenodo.org/record/1428064.
- ↑ Stollé, R.; Bergdoll, R.; Luther, M.; Auerhahn, A.; Wacker, W. (1930). "Über N-substituierte Oxindole und Isatine" (in German). J. Prakt. Chem. 128 (1): 1–43. doi:10.1002/prac.19301280101. https://zenodo.org/record/1428064.
- ↑ Sumpter, Ward C. (1944). "The Chemistry of Isatin". Chem. Rev. 34 (3): 393–434. doi:10.1021/cr60109a003.
- ↑ Sumpter, Ward C. (1945). "The Chemistry of Oxindole". Chem. Rev. 37 (3): 443–479. doi:10.1021/cr60118a003. PMID 21013427.
- ↑ Julian, Percy L.; Pikl, Josef (1935). "Studies in the Indole Series. IV. The Synthesis of d,l-Eserethole". J. Am. Chem. Soc. 57 (3): 563–566. doi:10.1021/ja01306a053.
- ↑ Rutenberg, M. W.; Horning, E. C. (1950). "1-Methyl-3-ethyloxindole (Oxindole, 3-ethyl-1-methyl)". Organic Syntheses 30: 62. doi:10.15227/orgsyn.030.0062. http://www.orgsyn.org/demo.aspx?prep=cv4p0620.; Collective Volume, 4, pp. 620
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