Movatterモバイル変換

Stollé synthesis

From Wikipedia, the free encyclopedia

TheStollé synthesis is a series ofchemical reactions that produceoxindoles fromanilines and α-haloacid chlorides (oroxalyl chloride).^[1]^[2]^[3]^[4]

The first step is anamide coupling, while the second step is aFriedel–Crafts reaction.^[5]^[6] An improved procedure has been developed.^[7]^[8]

^Stollé, R. (1913)."Über eine neue Methode zur DarstellungN-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)."ÜberN-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)."ÜberN-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.Bibcode:1935JAChS..57..563J.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.

Hidden categories: