Stollé synthesis

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]

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.

Zdroj:https://en.wikipedia.org?pojem=Stollé_synthesis
Text je dostupný za podmienok Creative Commons Attribution/Share-Alike License 3.0 Unported; prípadne za ďalších podmienok. Podrobnejšie informácie nájdete na stránke Podmienky použitia.

[1] 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.

[2] Stollé, R. (1914). "Über Phenyl-oxindol". Ber. (in German). 47 (2): 2120–2122. doi:10.1002/cber.191404702112.

[3] 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.

[4] 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.

[5] Sumpter, Ward C. (1944). "The Chemistry of Isatin". Chem. Rev. 34 (3): 393–434. doi:10.1021/cr60109a003.

[6] Sumpter, Ward C. (1945). "The Chemistry of Oxindole". Chem. Rev. 37 (3): 443–479. doi:10.1021/cr60118a003. PMID 21013427.

[7] 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.

[8] 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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

See also

References