Stollé synthesis

Stollé synthesis

The Stollé synthesis is a series of chemical reactions that produce oxindoles from anilines and α-haloacid chlorides (or oxalyl chloride). [Stollé, R. "Ber." 1913, "46", 3915.] [Stollé, R. "Ber." 1914, "47", 2120.] [Stollé, R. "J. Prakt. Chem." 1923, "105", 137.] [Stollé, R. "J. Prakt. Chem." 1930, "128", 1.]

The first step is an amide coupling, while the second step is a Friedel-Crafts reaction. [Sumpter, W. C. "Chem. Rev." 1944, "34", 396. (Review)] [Sumpter, W. C. "Chem. Rev." 1945, "37", 446. (Review)] An improved procedure has been developed. [Julian; Pikl "J. Am. Chem. Soc." 1935, "57", 563.] [Rutenberg, M. W.; Horning, E. C. "Organic Syntheses", Coll. Vol. 4, p.620 (1963); Vol. 30, p.62 (1950). ( [http://www.orgsyn.org/orgsyn/prep.asp?prep=cv4p0620 Article] )]

References

ee also

*Indole
*Hinsberg oxindole synthesis


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