From Wikipedia, the free encyclopedia
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 Stollé synthesis
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)" .
Ber. (in German). 46 (3): 3915–3916.
doi :
10.1002/cber.191304603186 .
^ Stollé, R. (1914).
"Über Phenyl-oxindol" .
Ber. (in German). 47 (2): 2120–2122.
doi :
10.1002/cber.191404702112 .
^ Stollé, R.; Bergdoll, R.; Luther, M.; Auerhahn, A.; Wacker, W. (1922).
"Über N -substituierte Oxindole und Isatine" .
J. Prakt. Chem. (in German). 105 (1): 137–148.
doi :
10.1002/prac.19221050111 .
^ Stollé, R.; Bergdoll, R.; Luther, M.; Auerhahn, A.; Wacker, W. (1930).
"Über N -substituierte Oxindole und Isatine" .
J. Prakt. Chem. (in German). 128 (1): 1–43.
doi :
10.1002/prac.19301280101 .
^ 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 ; Collected Volumes , vol. 4, p. 620 .